Questions Chapter 1-10
-
Upload
priyaranjan -
Category
Documents
-
view
218 -
download
0
Transcript of Questions Chapter 1-10
-
7/25/2019 Questions Chapter 1-10
1/107
SECTION - I : STRAIGHT OBJECTIVE TYPE
1.1 IUPAC name of compound
CI
Br
is
(A) 3-Bromo7-chloro-7ethyl-5-(1,1-dimethyethyl)-5-(2-methylpropyl)-3-methylnonane(B) 3-Bromo7-chloro-5-(1,1-dimethyethyl)-7-ethyl-3methyl-5-(2-methylpropyl)nonane(C) 3-Bromo7-chloro-7ethyl-3-,methyl-5-(1,1-dimethyethyl)-5-(2-methylpropyl)nonane(D) 3-Bromo-5-(1,1-dimethyethyl)-5-(2-methylpropyl)-7-chloro-7ethyl-5--3-methylnonane
1.2 Which of the following structure\s is the correct structure of 3-ethyl-5, 5-diisopropyl-7-methlnonane
(A) (B)
(C) (D)
1.3 The correct IUPAC name of the folllowing compound is
(A) 5,6-Diethyl-8-methyl dec-6-ene (B) 5,6-Diethyl-3-methyl dec-4-ene(C) 5,6-Diethyl-3-methyl dec-4-ene (D) 2,4,5-Triethylnon-3-ene
1.4 Correct IUPAC name of the following compound is :
HO
Br
(A) 3-(Hepta-2,4,6-trienyl)-4 bromo cyclopenta-2, 4, -dien-1-ol
(B) 7-(2-Bromo-4-hydroxy cyclopenta-1,4-dienyl)hepta-1,3,5-triene
General Organic Chemistry-I
(GOC-I)
1
-
7/25/2019 Questions Chapter 1-10
2/107
(C) 7-(5-Bromo-3-hydroxycyclopenta-1,4-dienyl)hepta-1,3,5-triene(D) 3-Bromo-4-(hepta-2,4,6-trienyl)cyclopenta-2,4-dien-1-oll
1.5 The IUPAC name of the compound
Br
will be :
(A) Tropyluim bromide (B) 1-Bromocyclohepta-2,4,6-triene(C) 3-Bromocyclohepta-1,4,6-triene (D) 7-Bromocyclohepta-1,3,5-triene
1.6 Correct IUPAC name of the co,pound H C CH O C3 2 O C CH CH2 3
O O(A) 4-(Ethyl methanolyonxy)phenylpropanoate(B) Ethyl 4-propanoyloxybenzenecarboxylate(C) 4-(1-Oxo-2-oxabutyl)phenylpropanoate
(D) 1-(1-Oxo-2-oxbutyl)-4-(1-oxopropoxy)benzene
1.7 Correct IUPAC name of the compound
Et
Me
O
O is
O
(A) 2-Ethyl-3-methylbut-2-ene-1,4-dioic anhydride(B) 3-Ethyl_2-methylbut-2-enedioic anhydride(C) 2-Ethyl-3-Methyl-1,4-diketobut-2-enoic anhydride
(D) 2-Ethyl-3-methylcyclopenatanoxy-1,4-dione
1.8 The IUPAC name of the following compound is
COCl
COOC H2 5
(A) 2-(Ethoxycarbonyl) benzalychloride (B) Ethyl 2-(Chloroformyl)benzoate(C) Ethyl 2-(chloromethanoyl)benzoate (D) Ethyl2-(Chorocarbonyl)benzene carboxylate.
1.9 IUAC name of
Cl
Br
CH3
C H52
(A) 4-Bromo-6-chloro-2-ethyl-1-methylcyclohex-1-ene(B) 5-Bromo-1-chloro-3-ethyl-2-methylcyclohex-2-ene(C) 5-Bromo-3-chloro-1-ethyl-2-methylcyclohex-1-ene(D) 1-Bromo-5-chloro-3-ethyl-4-methylcyclohex-3-ene
1.10 A hydrocarbon (R) has six membered ring in which there is no unsaturation. Two alkyl groupsare atttached to the ring adjacent to each other. One group has 3 carbon atoms with branchingat 1st carbon atom of chain and another has 4 carbon atoms. The larger alkyl group has mainchain of three carbon atoms of which second carbon is substituted. Correct IUPAC name ofcompound (R) is
(A) 1-(1-Methylethyl)-2-(1-methylpropyl)cyclohexane(B) 1-(2-Methylethyl)-2-(1-methylpropyl)cyclohexane
-
7/25/2019 Questions Chapter 1-10
3/107
(C) 1-(1-Methylethyl)-2-(2-methylpropyl)cyclohexane(D) 1-(1-Methylethyl)-2-butylcyclohexane
1.11 Identify the structure of x,
CH C CH3 C H + H C H + CH C C CH C H2 2
O O O O O O
CH3 CH3
CH3
H /Ni2
Zn/H O2
O3
X
(A) (B) (C) (D)
H C3
1.12 In the given sequence reaction which of the following is the correct structure of compounds A.
O O
OO
H
H+ HCHO
H / Ni2
(i) O3
(ii) Zn / H2O
A(C H )10 14
(A) (B) (C) (D)
H
1.13 For the following reactions sequenceHOOCCOOH
O3H2O2
C7H10H2 / Niexcess
Y
C7H12X
The structure consistent with X and Y are:
(A)
(B)
(C)
(D)
'Y' 'X'
-
7/25/2019 Questions Chapter 1-10
4/107
1.14 An organic hydrocarbon on oxidative ozonolysis produces oxalic acid and butanedioic acid. Itsstructure is
(A) (B) (C) (D)
1.15 CO
O
HCO
O
and are
(A) Position isomers (B) Chain isomers(C) Functional isomers (D) Metamers
1.16 In which reaction a chiral reactant is giving a chiral product.
C = O + H2 H C OHHint :
(D)
H Cl
C = O
CH3
H Cl
CH3
H / Ni2H CH CH2 3
CH = CH2
CH2OH
O / Zn / H O3 2
H C = C
HOC
CH3
(B)
H CHO
CH3H
HKMnO / OH /4
C C H2 5
CH3
H Reductive ozonolysis
(i) O
(ii) Zn / H O
3
2
1.17 Which of the following statements is true abnout the follownig conformer (X)?
I
CH3
COOH
I
COOH
(X)
CH3
(A) (X) is the most stable conformer of meso-2,3-Diiodo-2,3-dimethylbutanedioic acid
(B) The most stable conformation will beCH3
CH3
COOH
COOH
I
I
(Y)
(C) The dipole moment of (X)is not zero but that fo Y is zero.(D) None
1.18 An unsaturated hydrocarbon on jcomplete hydrogenation gives 1-isopropyl-3 methylcyclohexane,after ozonolysis it gives one mole of formaldehyde, one mole of acetone and one moleof2,4-Dioxohexanedial. The possible structure\s of the hydrocarbon maybe
-
7/25/2019 Questions Chapter 1-10
5/107
(A) (B) (C) (D)
1.19 How manyh assymmetric carbon atoms are present in
(i) 2-Dimethyl cyclohexane(ii) 3-Methyl cyclopentene(iii) 3-Methylcyclohexene(A) 2,1,1 (B) 1,1,1 (C) 2,0.2 (D) 2,0,1
1.20 Which of the following statements is not correct?(A) A compound whose molecule has D configuration will always be dextrorotatory(B) A compound whose molecule has D configuration may be dextrorotatory or levorotatory(C) A compound whose molecule has R configuration may be dexrotatory or levorotatory(D) A compound whose molecule has L configuration may be dextrorotatory or levorotatory
1.21 Identify the pair of enantiomers amongst the given pairs:
(A) D OH,
COOH
CH3
HOOC OH
CH3
D
(B) HO CH ,3
Ph
H
HO Ph
CH3
H
(C) H OH ,3
COOH
CH
HOOC CH3
OH
H
(D) H OH,
CH3
HO Ph
CH3
CH3 CH3
1.22 The stereochemical formula of deiastereomer 'Y' of optically active compound 'X' is:
X=2,3-Dihydroxbutanedioic acid.
(A) HOOC HOH
OH
H COOH
(B) HOOC H
OH
H
COOH
OH
(C) H OH
COOH
HO
COOH
H
(D) HO COOH
H
H
OH
COOH
SECTION-II : MULTIPLE CORRECT ANSWER TYPE1.23 Which of the followning statements are not correct?
(A) A meso compound has chiral centres but exhibits no optical activity(B) A racemic mixture is optically inctive becaure of two equal and opposite rotation of same
molecules in mixture.
(C) A meso compound has molecules which are superimpossable on their mirror images eventhough they contain chiral centres
(D) A meso compound is optically inctive because the rotation caused by any molecule iscancelled by and equal and opposite rotation caused by another molecules that is the mirrorimage of the first
1.24 Consider following compounds
OH
C H2 5(I)
OCH3
CH3(III)
OH
CH CH3
(II)
CH2OCH3
(IV)
-
7/25/2019 Questions Chapter 1-10
6/107
Choose the correct statement(s)from the following(A) I,II and III are functional isomers (B) I and II re position isomers(C) III and IV are chain isomers (D) III and IV are metamers
1.25 Which of the following statement\s is \are true about the following compounds
O
(I) (II) (III)O O
(A) (I)and (III)are structural isomers. (B) (I)and (II)are geometrical diastereomers(C) (II)and (III)are strukctureal isomers (D) (I)and (II)are jidentical
1.26 Which of the following is\are a meso compoumd.
(A)
OHOH
O
CH OH2
CH OH2 (B)
COOH
H
COOHNH2NH2H
(C)
CI
F
Br
CI
Br
F
COOH
(D)
COOH
H OH
HO H
1.27 Which of the following pair represents the correct relationshipI II
(A)
NH2
CI
OH CI OH
NH2
Relationship
(B)
Positional Isomers
Chain Isomer
(C)
(D)
NH C H3 7 H C N C H3 2 5
Functional Isomers
Metamer IsomersCH CH CH COCH3 2 2 3
O
CH CH3 2 2 3COCH CH
O
SECTION-III:REASONING TYPE
1.28 Statement-1:Restricted rotation about a bond is the necessary condition for geometricalisomerism.Statement-2:Two different orientations are possible due to restricted rotation about a bond iftheend groups are different.(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Statement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement -2 is True.
-
7/25/2019 Questions Chapter 1-10
7/107
1.29 Statement-1:Aracemic mixture of 2-Chloropropanoic acid is treated with excess of (+)-2-Butanol.The reaction can be represented as follows:
CH3CHCOOH + CH3CHCH2CH3 CH3CHCOOCHCH2CH3+CH3CHCH2CH3
CI OH(+)excess CI OH(+)(Left unreacted)
Statement-2:The solution kjof reaction mixture at time(t = 0), will be dexterorotatory becauseof (+)2-butanol(A) Statement-1 is True, Statement-2 is True; Statement-2 is a correct explanation for Statement-1(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Statement-1 is True, Statement-2 is False.(D) State,emt-1is False, Statement-2 is True.
SECTION-IV : TRUE & FALSE STATEMENT TYPE1.30 The products(ester)of following reactiongive diastereomers
Me
HD
Me
EtH
COOH + HO H SO2 4
Comprehension #1
Compound X(C7H14O4)on ozonolysis gives (Y) and (Z),(Z) is the aldhyde which gives only oneoxime with NH2-OH. On treatment with I2\NaOH,(Y)gives yellow solid CHI3alongwith compoundgiven below.
HO
HH OH
OH
H
COONa
CH OH2
When (X)is treated with D2\Ni, it gives two optically active compound.(V)and (W).
1.31 compound(V)and (W)are(A) Enantiomers (B) Diastereomers (C) Identical (D) Nuclear Isomers
1.32 Compound (Y)can give........ type of oximes on treatment with NH 2-OH(A) 2 (B) 6 (C) 8 (D) 7
1.33 Which of the following statement is true(A)'X' gives positive test with 2,4-DNP and Br2solution(B)Y gives positive with both 2,4-DNP and tollens reagent(C)Compound(V)give positive test with NaHCO3
(D)
CH3 NH2C
O is the isomeric amide of oxime of next higher homolog of Z.
Comprehension#2
Structural isomers have different covalent linkage of atoms. Stereoisomers are compounds thathave same sequence of covalent bonds but differ in the relative dispositions of their atoms in
space. Geometrical and optical isomers are the two important types of configurational isomers.The compound with double bonds or ring structure have restricated rotation, so exist in two
-
7/25/2019 Questions Chapter 1-10
8/107
geometrical forms. The double bonds in larger rings (ring size 10 carbon or large) can alsocause geometrical isomerism. The optical isomers rotate the plane of plane-polarised light. Asp3
hybridised carbon atom bearting four different types of substituents is called and asymmericcentre or chiral centre. A chiral object or molecule cannot be superimposed on its mirror image.Stereoisomers that are mirror images of each other are called diastereomers. Deastereomersw
have different physical properties.A racemic mixture is optically inctive and contains equal amounts of both the enantiomers .Resolution refers to method of separating a racemic mexture into two pure enantiomers. Amesocompound is and opticall incactive stereoisoker, which is achiral due to the presence ofand internalk plane of syummetry or centre of symmetry within the molecule.
1.34 The pair showing identical species is
H
H
COOH
OHOH
HOOC
(C) and
COOHOH
H OHHHOOC
CCH3
Cl
Br
H
CH3C
Cl
Br
Hand(D)
(B)H
D
OH
Br
Me
Et
D
H
Et
OH
Br
Me
and(A) H
Cl
H
Cl
and
1.35 Observe the following reaction
H
CH3
NH2
*+
HOOC CH3
Cl H
C*
(R')-1-Phenylethylamine (R+S)-2-Chloropropanoic acid
(R' R) + (R' S)(1)
(R')+ (R)
(R')+ (S)
(R'R)
(R'S)hydrolysis
hydrolysis
(3)
(3)
separation by
recrystallisation(2)
Which statement is not correct about the above observation.(A)The product mixture os step-1 is optically active(B)The products R'R and R' S have identical structural formul.(C)R'Ris nonsuperimposable on R' S(D)R'Rand R' S have same solubillity in water.
1.36 The number of chiral centres present in the following compound is
HH
OH
H
H
H
HO
O
OH
CH OH2
O
OHOH C2
H
H
OH H
OH
CH OH2
D (+) - Sucrose
-
7/25/2019 Questions Chapter 1-10
9/107
(A) 7 (B) 8 (C) 9 (D) 10
SECTION-VI:MATRIX-MATCH TYPE
1.37 Column I may match with more than one conditions of column II.
Column I Column II
Ph CH = CH Ph(A) (p) Ozonolysis followed by reaction withNH2 OH leads to more than one oximeproduct
(CH ) C = CH CH = Cl23
CH3
(B)
(q) Can exhibit geometrical isomers
CH = CH CH = CH2 2 (r) Compounds with this structure formula
can be separated into different fractionsupon fractional distillation
CHO CH CH CHO
OH OH(s) Is capable of showing stereoisomerism
1.38 Column I Column II
(A)HO
D
D
D
OH
CH3 OH
D
D
D
OH
H3C(p) can be separated by fractional
crystallisation
(B)CHO
C CCH3
CH3
CHO
CHO
C CCH3
CHO
CH3
(q) Can not be separated by
fractional crystallisation
(C)
COOH
OH
OHCOOH
H
H
H
HOH
OH
COOH
COOH
(r) Optically resolvable
Cl
OH3
OH2ID
Br
H
CH3
Br
CH2ClI
D
H
(D) (s) donot have identical boilling point
-
7/25/2019 Questions Chapter 1-10
10/107
SECTION-VII: SUBJECTIVE ANSWIR TYPE
SHORT SUBJECTIVE:
1.39 Total number of stereoisomes possible for molecule A will be
H C3 CH = CH CH = CH
1.40 A BCl / hv2Fractional
distillation
Number of possible fractions of B are:
1.41 The number of isomers for the compound with molecular formula C2HDFCI is :
1.42 Number of sp2
-sp2
sigma bonds in viven compound A is:
1.43 Write lowest molecular weight of saturated cyclic hydrocarbon which has four substtituents.Molecular weight=98.
-
7/25/2019 Questions Chapter 1-10
11/107
SECTION-I: STARINGT OBJECTIVE TYPE
2.1 Choose the correct statement
(A) I effect transfers e from one carbon atom to another
(B) I effect operates in both \p bond(C) I effect creates not charge in moecule(D) I effect cteates prtial cjarges and it is distance dependent
2.2 The correct stability order of following species is :
(x) (y) (z)
C
(w)
(A)x>Y>w>z (B)y>x>w>z (C)x>w>z>y (D)z>x>y>w
2.3 Which of the following does not represent the resonating structure of
(A) (B)
+
+ + (C) (D)
2.4 The most stable resonating structure of CH O = CH = CH3 2:
(A) (B) H C O = CH CH3 2 (C) H C O = CH CH3 2 (D) H C O = CH CH3 2+ + + +
2.5 Ordinarily the barrier to rotation about a carbon-carbon double bond is quite high but in compoundP double bond between two rings was observed by NMR to have a rotational energy barrier ofonly about 20 cal.\mol., showing that it has lot of single bond charcter.
nC H3 7
nC H3 7
The reason for this is(A) Double bond having partial triple bond charcter because of resonance(B) Doule bond undergo flipping(C) Double bond having very high single bond charcter because of aromaticity gained in both
three and five membered rings.
(D) +I effect of nC3H7groups makes double bond having partial single bond charcter.
General Organic Chemistry-II
(GOC-II)
2
-
7/25/2019 Questions Chapter 1-10
12/107
2.6 Most contributing structure in nitroethene is
(A) CH = CH N2+ O
O
CH = CH N2+ O
O
+ CH CH N2
+ O
O
+CH CH = N2
+ O
O
+(B) (C) (D)
2.7 In which of the followig molecules all the effects namely inductive, mesomeric and hyperconjjgationoperate:?
(A) Cl (B) CH3
CH3
(C) COCH3
CH3
(D)
2.8 Between
N
CH3CH3H3C +
N
HHH +
and
(l) (ll)
(A) N(I)has more 's' charcter in NCH3 bonds(B) N(II)has more 's' charcter in NH bonds(C) N(I)has less 's' charcter in NCH3 bonds(D) None of these
2.9 The acid strength order is:
O
O OH
OH
I II
OH
C
O
OHHO
III
C
O
CH3CH3
IV
(A)I> IV> II> III (B)III> I> II> IV (C)II >III> I>IV (D)I >III >II> IV
2.10 Acid strenght of the conjugate acids of the following are-
N NH N NH N
H
(l) (ll) (lll) (lV)
N
(A)I> II> III >IV (B)III> II> I> IV (C) IV> III> II> I (D)None of these
2.11 The acid dissociation constants of the following acids are given as under:Compound Ka
CICH2COOH 136 X 105
CH3CH2
CI
C HCOOH 139 X 105
CH3
CI
C HCH2COOH 8.9 x105
CI
C H3CHCH2COOH 2.96 x105
CH3CHCH2COOH 1.52 X 105
-
7/25/2019 Questions Chapter 1-10
13/107
From this data, the following obnservations can be made. Mark the correct statements for abovementioned compoumds.(i) The above variation in acidities of the above acids are due to inductive effect only.(ii) The above variation are both due to inductibve and resonance effects.(iii) Inductive effect varies shrply with distance.
(iv) -I effect of chlorine is not much.(A) i and ii (B) i and ii (C) ii and iii (D) iii and iv
2.12 The correct order of acidic strength is :
(l)
COOH
OH(ll)
COOH
OHOH(lll)
COOH
CH3
COOH
CH3
OH
(lV)
(A) III> IV> I> II (B) II> I> III> IV (C)II> III> I> IV (D)II> I> IV> III
2.13 Which one of the following reaction is not possible?(A) CH3COONa + HCI CH3COOH + NaCI(B) CH3SO3 H + H C = C Na CH3SONa + H C = C H(C) R C = C H + PhONa PhOH + R C = C Na(D) H C = C H + NaH2 H C = C Na + NH3
2.14 IfS
O
P
OQR
H
CH3is mixed with NaOH solution. Acid base reaction occurs and HO snatches H from
organic molecule. Which carbon will loose H easily?
(A) P (B) Q (C) R (D) S
2.15 OH
COOH (x)OH
COOH (y)
(z) HOOC
HO
The correct acidic strength order of acidic hydrogen x,y and z is respectively.(A) x > z > y (B) x > y > z (C) z > y > x (D) y > z > x
2.16 H
N(p)
NH(r)
N
H
OO
(q)
The correct basicity order of atoms p,q and r is :(A) p > q > r (B) r > p > q (C) r > q > p (D) q > p > r
-
7/25/2019 Questions Chapter 1-10
14/107
2.17N
HI
N
H
II
O
N
H
III
N
IV
The order of basicity is(A) I > IV > II > III (B) I > II > IV > III(C) III > II > IV > I (D) II > III > IV > I
2.18 The correct basic strengtyh order is:
C
O
CH3
H2NC
O
CH2
NH2CH3
NH
ONH
C
O
CH3
I II III IV
(A) I > II > IV > III (B) IV > III > II > I(C) III > II > IV > I (D) III > IV > II > I
2.19 The correct order of acid and basic strength for the following pair of compounds should be?COOH COOH
CH3and
COOH COOHCH3
andAcid strength :
(I) (II) (III) (IV)
;
Basic strength :
NH2 NH2CH3
and
NH2 NH2CH3
and
(V) (VI) (VII) (VIII)
;
(A) I > II ; III > IV ; V > VI ; VII < VIII(B) I < II ; III > IV ; V < VI ; VII > VIII(C) I > II ; III > IV ; V > VI ; VII > VIII(D) I < II ; III > IV ; V < VI ; VII < VIII
2.20 Observe the foolowing reaction :
COOH
+
COONa OH
NO2
+
O Na
NO2
+
OH
NO2
ONa
NO2
+ NaHCO3 + H CO32
ONa OH
+ H CO32 + NaHCO3
-
7/25/2019 Questions Chapter 1-10
15/107
Which of the following is the correct order of acid strength :
COOH
(A)
OH
NO2
OH
> > H CO >2 3
COOH
(B)
OH
NO2
OH
> > > H CO2 3
COOH
(C)
OH
NO2
OH
> >H CO2 3 >
COOH
(D)
OH
NO2
OH
> > H CO2 3>
2.21. Which of the following statement is CORRECT regarding the inductive effect?(A) electron-donating inductive effect (+ l effect) is generally more powerfull than electron-
withdrawing inductive effect (l effet t)(B) it implies the shifting of s electrons from more eletronegative atom to the lesser eletronegative
atom in a molecule.(C) it implies the shifting of r electrons from less electronegativbe atom to the more electronegative
atom in a molecule(D) it increases with increase in distance.
2.22 Which of the following statement regarding resonance is NOT correct?(A) the different resonating structures of a molecule have fixed arrangement of atomic nuclei.(B) the different resonbating strcutues differ in the arrangement of electrons.(C) the hybrid structure has equal contribution from all athe resonationg structures always.(D) None of the individual resonating structure explains all charcteristics of the molecule.
SECTION-II: MULTIPLE CORRECT ANSWER TYPE2.23 Which of the following statements would be incorrect about this compoud?
NO2
NO2
NO2
Br
1 5
3
(A) All three C N bond are of same length(B) C1 N and C3 N bonds are of same length but longer than C 3 N bond(C) C1 N and C5 N bonds are of same length but longer than C 3 N bond
(D) C1 N and C3 N bonds are of different length but both are longer than C5 N bond
2.24 Choose the incorrect statement:(A) Salicylic acid (oHydroxybenzoic acid) is much stronger than its m-,p-isomers and benzoic
acid itself.(B) Acidity of salicylic acid is due to steric inbibition of re3sonance, as OH group forces
COOH out of the plane of ring(C) The orbitals which are in the same plane take part in resonance(D) All the resonating structures have real existence
2.25 In which of the following pairs the first one is the stronger base than second.
(A) CH3CHOO, HCOO (B) HO,NH(C) CH2=CH: , H C = C (D) CH3NH2, CH3,OH
-
7/25/2019 Questions Chapter 1-10
16/107
2.26 Which statement among the followijng are corect?(A) Hydration effect stabilises dimethyl ammonium ion more than trimethyl ammonium ion(B) In chlorobenzene as there is no hydration effect so, trimethyl ammonium ion gets less
stabillised than dimethyl ammonium ion(C) RCONH2 is feebly acidic with respect to RCOOH
(D) CH3> NH2> OH is the basicityh order
2.27 Resonance structures of a molecule should have.(A) Identical arrangement of atoms (B) Nearly the same energy content(C) The same number of paired electrons (D) Identical bonding
SECTION-III : ASSERTION AND REASON TYPE
2.28 Statement-1:Ortho iodobenzoic acid is strongest acid among all ortho halobenzoic acids.Statement-2: Iodine exerts maximum ortho effect (steric effect) so the acid weakening resonaceeffect of aromatic romg os decreased/(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True
2.29 Statement-1:Salicylic acid is much stronger than its m-, p-isomers adnsf benzoic acid itself.Statement-2:It is due to steric inhibition of resonance, as OH group forces COOH out ofthe plane of ringt.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1
(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True
SECTION - IV : TURE AND FALSE TYPE
2.30 Give the correct order of initials T or F following statements. Use T if statement is true and Fif it is false .S1 : Both the C O bond lengths in HCOOK are equalsNH2both have same dipole moment value.
S2 : HO OH NH2 NH2and
S3: Propyl chloride shows maximum dipolemoment in anti conformer.
S4 :N
N
NH2
is stronger base then
(A) T T T T (B) T F T F (C) T T F F (D) F F T T
SECTION - V : COMPREHENSION TYPE
comprehension # 1
The concept of resonance explains various properties of compounds. The molecules withconjugated system of p bons, are stabilized by resonace and have low heat of hydrogenation.
-
7/25/2019 Questions Chapter 1-10
17/107
Hyperconjugative stabilization also decreases heat of hydrogenation. In aromatic rings a functionalgroup with a lone pair of electron exerts +m effect. Some functional groups like NO, NC,CH= CH2 can function both as electron releasing (+m, +R) or electron withdrawing (m, R)groups. More extended conjugation provides more stabilization.
2.31 The correct heat of hydrogenation order is(p) 1,3-Pentadiene (q) 1,3-Butadiene(r) 2,3-Dimethyl-1, 3-butadiene (s) Propadiene(A) p > q > r > s (B) s > q > p > r (C) q > s > p > r (D) s > q > p > r
2.32 The most stable carbocation is
(A)
(C)
(B)
(D)
2.33 The most stable resonating structure of following compound is O = N N = O
N = OO N(A)
N = OO = N(C)
N OO N(B)
N = OO N(D)
Comprehension # 2
The key concepts of resonance are :Resonance occurs because of the overlaping of orbitals. Double onds are made up of pi bonds,formed from the overlap of 2p orbitals. The electrons in these pi orbitals will be spread over mor4than two atoms, and hence are delocalized . Both paired and unshared electrons may bedelocalized , but all the electrons must be conjugated in a pi system. If the orbitals do not overlap(such as in orthogonal orbitals) the sturctures are not true resonance structures and do not mix.Molecles or species with resonance structures are generally considered to be more stable thanthose without them. The delocalization of the electrons lower the orbital energies, imparting thisthis stability. The resonhance in benzene gives rise to the property of aromaticity . The gain instability is called the resonance energy. All resonance structures for the same molecute musthave the same sigma framework (sigma bond form from the "head on' overlap of hybridizedorbitals). furthermore, they must be correct Lewis structures with the same number ofelectrons(and consquent charge) as well as the same number of unpaired electrons.Resonancestructures with arbitrary separation of chargfe of charge are unimportant, as arethose with fewer covalent bonds . theese unimportant resonance structures only contributeminimum (or not at all) to the overall. From the above theory of resonance answer the followings.
2.34 The correct resonation structre of 1, 3-butakiene is -
(A) CH CH CH = CH2 2
(C) CH CH = CH CH2 2
+
+
(B) CH CH CH = CH2 2
(D) None of these
+
-
7/25/2019 Questions Chapter 1-10
18/107
2.35 The correct stable resonating structure of benzene is -
(B)
(A) +
+
(C)
+
+
+ (D) None of these
2.36 Which resonating sturcture is not correct
CH =CHCH2 2(A) CH CH = CH2 2++
(C) CH CNH3 CH C=NH3
O O
NH CNH2 2
+NH2
NH C = NH2 2
NH2
(B)
(D)
N
H
N
H
+
SECTION - VI : MATRIX - MATCH TYPE
2.37 Match the following
(A)
CH3
CH3
CH3
CH3N
(B)
Cl
Cl
O
N=O+
O N2
(C)
CH3
CH3
NH2O N2
(C)
CH3
CH3
NO N2CH3
CH3
(p) is more
(q) is less
(r) Larger C N compared to C NO2
(s) Larger C N bond largteer compared to aniline
-
7/25/2019 Questions Chapter 1-10
19/107
2.38 Match the pKavalues with the given compoundsAcid pK a
NO2
OH
NO2
NO2
(A)
(B)CH COOH3
(C)
O
O
NH
Phthalimide
COOH
(D)
(p) 4
(q) 9
(r) 5
(s) 0.74
SECTION - VII : SUBJECTIVE ANSWER TYPE
SHORT SUBJECTIVE :
2.39 For the compound :
OH
Give the number 1 for presence of resonance only, 2 for presence of resonance andhyperconjugation only, 3 for presence of resonance, hyperconjugation and inductive effect and4 for presence of resonance hyperconjugation, inductive effect and electromaric efffect.
2.40
OH
CHCH
2
Br
Br
OHC
HOOC
x mole NH2
value of X used for complition of reaction will be :
2.41 Incorrect statement among these four :(i) I effect is prermanent polarisation of sigma bond pair of electrons in the molecule.(ii) In resonation structures the hybridisation of atoms do not change.(iii) In Hyperconjugative structures the hybridisation of carbon atom change.(iv) Presence of methyl group on an anion always destabilises ith anion.
2.42 Maximum number of hyperconjugtation forms of structure :
-
7/25/2019 Questions Chapter 1-10
20/107
2.43 In the following set of resonationg structures which sets have the second resonation structuremore contributing than first :
NH2
OCH3+
NH2
OCH3
+
N
O+
N
O
O OOO
+ClCl
N
O
N
O
I :
II :
III :
IV :
-
7/25/2019 Questions Chapter 1-10
21/107
SECTION - I : STRAIGHT OBJECTIVE TYPE
3.1 Read the following road map carefully
CH3PhCH2CHOK + gas
EtOTsII
CH3PhCH2CHOTs
IV C H52 OK
CH3
PhCH2CHOH
K I III TsCl1-Phenyl-2-propanol
S.R = +33.02
CH3
PhCH2CHOC H2 5ethyl1phenyl2propylether
CH3
PhCH2CHOC H2 5Ethyl1phenyl2propylether
(A) Both the ethers obtained by the two routes have opposite but equal optical rotation.(B) One of the ether is obtained as a recemic mixture.(C) Step II & III both are SN2 reaction and both have inversion.
(D) Step II has inversion but step III has retention.
3.2 A compond A has the molecular formula C5H9CI. It does not react with bromine in crabontetrachloride. On treatement with strong base it produces a single compound B. B shas amolecular formula C5H8 and reacts with bromine in carbon tetrachloride. ozonolysis of B producesa compound cC which has a molecular formula C5H8O2. Which of the following structures isthat of A?
(A)Cl
(B)
Cl
CH3
(C)
Cl
CH3 (D)
Cl
3.3 2 4Me SONaOH
PhOH P, P is
(A) PhOSO2OMe (B) PhOMe (C) PhOSO2OPh (D) PhMe
3.4
P =Br
COCH COCH2 3
HD
NaOHP
Reaction Mechanism3
-
7/25/2019 Questions Chapter 1-10
22/107
Which of the following statement is correct
P = C CH3
O
O
HD
(B)P =OH
COCH COCH2 3
D
(A)
H
P =
O
D
(D)
H
P =(C) CH3
O
O
DH
3.5
OH
Br
NaOH
(B)
O
(C)
OH
OH
(D)O
(A)
OH
OH
3.6CH CH SH3 2
(i) CH O3(ii) ethylene oxide(iii) H O2
Product, Product is :
(A) CH CH S CH 3 2 2 CH OH2
( ) CH CH CH C O3 2 2 CH OH2 ( ) CH CH D S3 2
( ) CH CHB O3 2
CH2
CH2
3.7 Br
Ph + Ph CH NH2 2
O
EtOProduct, Product is
(A)
OEt
Ph
O
(B) Ph
O
NH Ph
(D) Ph NH Ph(C)
Br
Ph
OH
NH Ph
3.8 In the reaction A.
OHOH
CH3
CH3conc. H SO2 4
The product is -
-
7/25/2019 Questions Chapter 1-10
23/107
-
7/25/2019 Questions Chapter 1-10
24/107
3.11 The products of hydrolysis ofO C H2 5O
, isH O3
(A) HOCH2CH2CH2CH2 CHO + CH3CHO (B) HOCH2CH2CH2CH2OH + CH3CHO(C) HOCH2CH2CH2CH2CHO + C2H5OH (D) HOCH2CH2CH2CH2CH2OH + C2H5OH
3.12
CH OH2
A.H SO2 4/H The product A is :
CH HSO2 4 CH2 CH2CH2
(A) (B) (C) (D)
OH
3.13 (CH3)3CCI + (CH3)3COK+
Product(A) SN Product will be more (B) E2Product will be more(C) both will be same (D) None of these
3.14 Neopentyl iodide is treated with aq. AgNO3solution, a yellow precipitate is formed along withother compound which is
(A) (CH ) CCH ONO3 2 23 (B) (CH ) C CH CH3 2 2 3
OH
(C) (CH ) CCH OH3 3 2 (D) (CH ) CCH CH3 2 2 3
ONO2
3.15 The major end product of the following reaction is
OH
CH Cl2
H C3
aq. AgNO3
OHH C3
C OHH2
(A)
CH3
H3C
O(B) (C)H3C O (D)
CH3
O
3.16 The major product P of the following reaction is
NH2 CH3
CH CH = C
CH3
NH2(D)
NH2 CH3
CH CH CH
CH3
NH2(C)
OCH3
NH2 CH3
CH CH C2
CH3
OCH3
NH2(B)
NH2 CH3
C CH CH2
CH3
NH2(A)
OCH3
NH2 CH3
CH CH CH
CH3
NH2
Cl
CH OH3 (P)
-
7/25/2019 Questions Chapter 1-10
25/107
3.17 The product of following reacting is
14
Ar
O
OH
(A)
14
ArO
O
H O3
14
OH
(C) + ArOH
O
14 + ArOH
OH
O
(B)
14
O
(D) + ArOH
O
3.18
O
CH2H2C14 H /H O
+ 182
Which can not be the product.
H C214
CH2
18OHOH
(A)
CH214
CH2
18OH OH
(B)
CH2 CH2
18OH
(C)18
OH(D) A and B both
3.19 The correct order of SN2 \ E2 ration for the % yield of product of the following halide is -
CH CH C CH3 3
Ph
I
CH CH CH CH3 3
IPh
CH CH 3 I2 CH CH CH CH3 3(P) (Q) (R) (S)
I
(A) R > S > Q > P (B) R > Q > S > P (C) P > R > S > Q (D) Q > P > R > S
3.20 The poduct in the given reaction is
H ONa +
Me
Ph
H Me
Ph
Br
I II
P
H O
Me
Ph
Me
Ph
H
(A)
H O
Ph
Me
Me
H
(C)
Ph
H O
Me
Ph Me
Ph
H
(B)
H O
Me
Ph H
Me
Ph
(B)
-
7/25/2019 Questions Chapter 1-10
26/107
3.21
Ph
reaction Rearranged most stable Carbocation is
Ph Ph PhPh
(A) (B) (C) (D)
3.22 H Br
Ag+Rearranged Carbocation + AgBr
Rearranged carbocation is :
+(D)(C)(B)(A)
CH3
SECTION - II : MULTIPLE CORRECT ANSWER TYPE
3.23 The correct statement(s) about solvent effect is\are :(A) Decreasing solvent polarty causes a large increase in therate of the SN2attack by ammonia
on an alkyl halide
RX + NH3 RNH3 + X+
(B) Increasing solvent polarity causes a large decrease in the rate of the SN2attack by hydroxideion on trimethyl sulphonmium ion
HO (C+ H3 3) S CH OH + (CH ) S3 3 3
DMSTrimethylsulphonium
ion
(C) Increasing solvent polarty causes a small decrease in the rat3e of the SN2 attack bytrimethylamins on trimethylsulfonium ion.
(CH ) N (C3 3 3+ H ) S3 CH N(CH ) + (CH ) S3 3 3 3 2+ +
(D) all ar3e incorrect
3.24 Which of the following reaction(s) is\are posible
(A) CH C ClCH NEt3 2 2H CH C (NEt )CH OH3 2 2HOH
(B) Either CH C3 H C H SEt or CH CH(sEt)CH OH2 3 2 CH C ClCH3 2H SEtHCl
OH
(C) Treatment of either epoxide I or epoxide II with aqueous OHgives the same product III
CH CH CH CH Br3 2 CH CH CH CH3 2or
O BrI II III
O
CH CH CH CH3 2 OH
O
OH
-
7/25/2019 Questions Chapter 1-10
27/107
(D)
OH
OEt
OH
OEt
+
OH
OEtEtOH
EtO
3.25OH
OH
NaOH
1eq P Q R 'S'O
CH CCl2
Cl
NaOH LiAlH4
O
O
O
R =(A)
O
Q =
OH
C = O
CH Cl2(C)
Q =OH
CH C Cl2
O(B)
S =
OH
OH
OH(D)
3.26OH
NH2
CH3C H6 4Ph
H
Ph
?HNO2
H
Ph
O
Ph
pCH C3 6 5H O Ph
HPh
pCH C3 6 5H
(A) (B)
H
Ph
O
Ph
pCH C3 6 5H (C)Ph O
HPh
pCH C3 6 5H
(D)
3.27 Which of the following reaction will go faster if the concentration of the nucleophile is increased?
H Br
+ CH O3
(CH ) CCl3 3 CH COOH3
H O2
+ CH S3
Br
Br Acetone
KI
(A) (B)
SECTION - III : ASSERTION AND REASON TYPE
3.28 Statement-1 : (CH ) C CH3 3
OH
CH3
(CH ) CCH=CH +3 3 2 CH3
CH3
CH3
CH3C=C + CH2=C
CH3
CH(CH3)2
H SO2 4
40% 20% 40%
Statement-2 :It follows Hofmann's elimination by E2.
-
7/25/2019 Questions Chapter 1-10
28/107
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True
3.29 Statement-1 : Ethers are prepared from alcohols in acid medium through SN1or SN
2mechanismsdepending upon nature of alcohol.
Statement-2 : ROH + H+ R OH2+
R O
H
R OH2+
R O R + H O2 ROR + H O3+
slow +
H
or, R OH + H+
R R + H O+
2OH2+
R + O R R O R+ +
slow
H H
R OR + H O3+H O2
fast
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True
SECTION - IV : TRUE AND FALSE TYPE
3.30Ph
OH
CH3 PhCH3 (Elimination follows E mechanism.)1H SO2 4
Heat
SECTION - V : COMPREHENSION TYPE
Comprehension # 1
Read the following reaction
O
H+P
Cl2
hQ R S T
NaOEt / NBS NaOH
3.31 Compound 'T' is
OH
OH
OH
OH
OH
HO
OH
OH
(A) (B) (C) (D)
-
7/25/2019 Questions Chapter 1-10
29/107
3.32 Compound 'Q' is
OlOH
Cl
OH
Cl
OH
Cl
(A) (B) (C) (D)
3.33 When treation 'S' with strong base, product obtained is
OH OH OHOH
Br
Comprehension # 2A hydrocarbon (X) of the formula C6H12 does not react with bromine water but reacts withbromine in presence of light, forming compound (Y) . Compound (Y) on treatment with A|c. KOHgives compound [Z] which on ozonolysos gives (T) of the formula C6H10O2. compound (Treduces Tollens reagent and gives compound (W).(W) gives iodoform t4st and produce compound(U) which when heated with P2O5 forms a cyclic anhydride (V).
3.34 Compound V isO
O
O
CH3
O
O
O
CH C CH 3 2 CH CH = O2
O
(A) (B)
(C) (D) CHO CH = CH CHO
3.35 Compound W is
(A) COOH (CH ) COOH2 2 (B)COOH
COOH
(C)COOH
COCH3(D) CH CH CH COOH3 2
CH = O
3.36 Compound 'X' is
(A)
(C)
(B)
(D)
CH3CH3
CH3
CH3 CH3
-
7/25/2019 Questions Chapter 1-10
30/107
SECTION - VI : MATRIX - MATCH TYPE
3.37 Match the column I with column II
CH3H
ClPh
C = CKNH2
CH3
OH
Ph
HSOCl2
CH3N
CH3
CH3
C
O
Ph +NaOH
CH CH CH2 2 3
CH NCH CH3 2 3CH3
CH2CH3
+ NaOH
(P) -elimination
(Q) SN2
(R) -elimination
(S) SN1
(Y)
(Z)
(W)
(X)
Column - ( )
Reactions
I Column - ( )
Reactions
II
3.38
CH CH CH3 2 2
CH CH2 3
CBr + H O2
H C3
CH CH2 3
CBr + H O2
H C3
CH =CHC Cl + SH / (CH COCH2 3 3)
CH3
CH3
(A)
(B) CH CHDCl + OH3
(C)
(D)
(p) Retention
(q) Racemisation
(r) Inversion
(s) Product with -bond shift
Substrate Stereochemistry of product
-
7/25/2019 Questions Chapter 1-10
31/107
SECTION - VII : SUBJECTIVE ANSWER TYPE
SHORT SUBJECTIVE :
3.39 Correct statement about nucleophiles and leaving groups is/are
(i) Nucleoghiles have an unshared electron pair and can make use of theis to react with andelectron rich species.
(ii) The nucleophillicity of an element generally inhcreases on goiing left to right in periodictable.
(iii) A nucleophile is an electron deficient species(iv) Leaving group ability kincreased in moving from L R and T B in periodic table.
3.40CH CH3 CCH Br2
CH3CH3
CH3NaOH/H O2
Which of the following stat4ements is incorrect about the given reaction
(i) The reation is SN1 reaction(ii) The reaction intermediate is planar (sp2)(iii) The major product will be 2-ethyl-3-methylbutan-2-ol(iv) The major product has two stereogenic centre
3.41 which of the following will not give SN1reaction with aq. AgNO3.
(i) (ii)CH Br2
Br
Ph
PhBrPh
Ph
Br
(iii) (iv)
Br
3.42 In the given reaction following products are expected.
CH Br2CH3
+
CH2OCH3
CH3
OCH3
+ ++
OCH3
(I) (II) (III) (IV) (V)
CH OH3
Which observetions seen to be incorrect(i) Ist is the major product obtained by E1 reaction(ii) IV is the major product obtained by SN1 reaction(iii) formation of II or V involves a strained carbocation intermediate(iv) In the solvolysis reactions a carbocation intermediate is formed.
3.43 Observe the following flow chart and answer the number of x,y, z, w.
PositionalIsomers = (X)
MonochloridesIsopentane
TotalIsomers = (Y)
Total number of 1 alcohols = (Z)including stereoisomers
KOH/DMSO
(SN )2
X Y Z
-
7/25/2019 Questions Chapter 1-10
32/107
SECTION - I : STRAIGHT OBJECTIVE TYPE
4.1 2-Phenylcycloprop-2-en-1-one is allowed to react with phenylmagnesium bromide and kthe reactionmixture is hydrolysed with prechloric acid. The product formed is
(A) Ph C C CHO
Ph
OHO
(B)
Ph
Ph
O
(C)OH
Ph
Ph
Ph
Ph
(D)
4.2 Which of the following reactions will give 2 chiral alcohol as one or more of major organicproducts?
(A)
H
D
CH3
MgIO2 H O3 (B) CH MgI3 + H C OCH
O
CH3
C H2 5H O3
(excess)
(C)
H
CH3
MgBr + CH2
O
CH2
H O3(D) None
4.3CH3 C C CH3
O O
PhMgBr
(excess)
H O2 No of product (X)Fractional distillation
no. of fractios (Y)
(A) 3,2 (B)3,3 (C) 4,2 (D) 4,3
4.4 The end product of following reaction is
O
O
OCH MgBr3 PhMgBr
(1) (2) (3)
H
(A) ,-diketone (B) -Hydroxy acid (C)1,2-Diol (D) -Hydroxy acid
4.5 Observe the following reaction sequence
X Br / hv2 Y Mg / Ether Z
O
Wdil.H SO2 4 U
O /Zn/H O3 2 O
X can be
(A) (B) (C) (D)CH3
Grignard Reagent
Reduction & Alkane4
-
7/25/2019 Questions Chapter 1-10
33/107
4.6
O(x) CH OH2
pyridine,
SOCl2 Mg
(C H ) O2 5 2 H+
O
CH C(CH )2 3 2
Product
Product of the reaction is
CH C CH CH2 2 3
OH
CH3
O CH C CH2 2H C( )3O
O
CH C H2 H C O2 O
CH3
CH3
CH C H2 C OH2O
CH3
CH3
(A) (B)
(D)(C)
4.7 Observe the following sequence of reactions.
CH CH CH3 2 3 (X) (Y)(1)Br / hv2
(2)
Mg/ether
(3)
CH Br3(4)
Cl / hv2
(5)
CH OH3(Z) (W) (R)
The product R is :
(A) CH CH 3 CH OCH (B) CH CH CH CH OH (C) CH CCH (D) CH C CH2 3 3 2 2 2 3 3 3 3
CH3 CH3 CH3
OHOCH3
4.8Ph N = C = O
(i) CH MgBr3(i ) Hi O2
LiAlH4P Q
(A) P is PhNHC CH and Q is PhNHCH CH3 2 3
( ) P is Ph NH CH and Q is HB N3 3
O
( ) P isC PhN=C OH and Q is Ph NH CH3
CH3
( ) P isD Ph NH CH and Q is Ph NH C CH3CH H 3
CH3OH3
4.9 Which of the following reduction methods is not suitable for preparing and alcohol?
(A) CH COOC H +3 2 5 NaBH4
( )C CH C O3 H C Cl+2 LiAlB4
( )B CH COOC H +3 2 5 Na/EtoH
( ) CH COO HD H +3 2Ni
4.10 C C C C
Ph CH
Br H
C = CH
CH Ph
Br
Li / NH3 Br2 (1equivalent)X,
'X' is :
(A) (B) (C) both (D) none of these
-
7/25/2019 Questions Chapter 1-10
34/107
4.11 Compound
OO
O
N
C
ClO
on reduction with LiAIH4produces
HON
CH OH2
CH OH2
CH OH2
(A)
HOO
OH
N
CH OH2
(B)O
OH
N
CH OH2
(C)N
CH OH2
CH OH2
CH OH2(D)
4.12 Which one is the correct energy profile for CI reaction ?
(A)
R.coord
Energy
(B)
R.coord
Energy
(C)
R.coord
Energy
(D) All of these
4.13 Which of the following is correct statement regarding relative acidic charcter of cyuclopropaneand propane ?(A) Cyclopropane is more acidic than propane(B) Propane is more acidic than cyclopropane(C) Both are equclly acidic(D) Bothe are neutral
4.14
No . of products and No. of fractions are respectively
(A) 6,5 (B) 6,4 (C) 5,4 (D) 6,3
4.15 Which of the following is correct potential energy diagram for the given chin propagatiog step.
CH H+F3B.E.=435kJ/mol
CH + H F3B.E.=569kJ/mol
= 32 kcal/mol
-
7/25/2019 Questions Chapter 1-10
35/107
4.16 Consider the following reaction
CH CH3 CHCH + Br3
D CH3
'X' + HBr, X can be
CH CH3 CHCH2
CH3D
CH CH3 CCH3
CH3D
CH C3 CHCH3
CH3D
CH CH3 CHCH3
CH3
(A) (B) (C) (D)
SECTION - II : MULTIPLE CORRECT ANSWER TYPE
4.17 Br
Mg NBSBA C D E + F
Zn
AgNO / H O3 2 O / H O3 214
(i) CH COCH3 3(ii) H(iii)
(A) Product C is
Br14
(A) Product D is
OH14 OHOOH
O 14
&only (D) F is
(B) E is CH = O & CH = O2 214
4.18
Ph CH CH CH2 3
CH3
(monochlorination)
Cl2 / h
Which statements is /are correct about photochemical chlorination of theabove compound [Morethan one correct](A) The major product wil be chiral carbon atom having optically inactive compound(B) The intermediate free radical of the major product is resonance stabilised(C) The intermediate free radical is tertiary(D) THe intermediate free redical is planer , and stabilised by only hyperconjugation
4.19 Which reaction is/are correct.
(A)C N
tertiary alcohol(i) Mg / Ether
(ii) H O3
(B)
Cl COOH
Mg
ether
CO2 H O3+
F
Cl
MgF
MgCl
Mg
ether(C)
(D) + CH C3
O
CH CH MgBr3
HO C C CH3
H O3
+
+
-
7/25/2019 Questions Chapter 1-10
36/107
4.20 Point out the following incorrect Grignard synthesis.
N
H
Br
N
H
CH Ph
OH
(i) Mg, ether
(ii) Ph CH = O
(iii) H O3
Br
OO
HOCH2
OO
MgBr(C) OH
(B)
(A)
(i) Mg, ether
(ii) PhCH = O
(iii) H O3
OH
(D)
O CH CH2 3HO
OH
(i) CH C CH3 3
(i i) H O3
O
(i) CH CH MgBr (1eq.)3 2
(i i) H O3
SECTION - III : ASSERTION AND REASON TYPE
4.21 Stetement-1 :Cyclopropane has the highest heat of combustion per methylene group.Statement-2 :Its potential energy is raised by angle strain.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Satement-1 is True, Statement-2 is False.
(D) Statement-1 is False, Statement-2 is True.
4.22 Statement-1 :Branched alkanes have lower boiling point than their unbranched isomers.Statement-2 :Branched alkanes has relatively small surface area, so less London's dispersionforce act among molecules.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True
4.23 Statement-1: Alkanes float on the surface of waterStatement-2 :Density of alkanes is in the ranbe of 0.6 0.9 g/ml, which is lower than water.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True
4.24 Statement-1 :Grignard reagent can be prepared in all nonpolar solvent.Statement-2 :Diethyl ether solvates the Grignard reagent.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True
-
7/25/2019 Questions Chapter 1-10
37/107
4.25 Statement-1 : The preparation of G.R. occurs in solution phase.Statement-2 :Teh reaction will be explosive in solid phase. GR. is stable only in solution phase.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1
(C) Satement-1 is True, Statement-2 is False(D) Statement-1 is False, Statement-2 is True
SECTION - IV : TRUE AND FALSE TYPE
4.26 Observe the following natural product and choose the correct statement
(x)HOOC
COOCH3
C H56
N (w)H
(y) O N2O(z)
O(r)
(1) LiAIH4will reduced x, y, z, w, r(2) NaBH4will reduced r(3) Na/C2H5OH will reduced r, w(4) (CH3)2CHOH + [(CH3)2CHO]3AI, (MPV) will reduced r(A) TFTF (B) TTTT (C) FTFT (D) FFFT
4.27 Diethyl ether is the solvent for Griganrd reagent but not for RLi, because RLi reacts withC2H5OC2H5 and givesw CH2 = CH2.
SECTION - V : COMPREHENSION TYPE
Comprehension # 1
Read teh following reaction
CH CH P QMg
Ether
NaOClR S
Cl
2CH CHO2
KOH NaOHH O2
T(ii) Dil.KMnO4
(i) H / Pd. BaSO2 4
4.28 'S' in the above reaction
(A) CC
CH2O
H
CH2
OH
(B) C
C
CH2O
H
MgBr
(C)
C
CMgBr
CH2OH
OHH(D)
C
C
OHH
CH2 OH
HHO
CH2 OH
4.29 'U' is
H OH
H
H
H
OH
OH
OH
CH OH2
CH OH2
(A)
H OH
H
H
H
OH
HO
HO
CH OH2
CH OH2
(B)
H OHHO
OH
OH
H
H
H
CH OH2
CH OH2
(B) OHH
COOH
CH OH2
(D)
-
7/25/2019 Questions Chapter 1-10
38/107
4.30 'Q' is(A) CIMgC CMgCI (B) CH C MgCI(C) CIOC CMGCI (D) CIOC COCI
Comprehension # 2
considering the following reations(I,II,III)and give your answer for following questions
HO CCl
O
(i) CH MgBr3
(ii) H O3+
COEt
O
(i) CH MgBr (excess)3
(ii) H O3+
CH Cl2
EtO C OEt
O
(i) Ph MgBr (excess)
(ii) H+
(a)
EtO C OEt
O(i) CH MgBr (excess)3
(ii) H+
(b)
H C OEt
O(i) Ph MgBr (excess)
(ii) H+(c)
H C OEt
O(i) CH MgBr (excess)3
(ii) H+
(d)
ClCH COOEt2
(i) CH MgBr (excess)3
(ii) H+
(e)
4.31 If CH3MgBr is taken in excess in reaction (I), how many moles of CH3MgBr will be consumedin reaction (I)
(A) 2 (B) 3 (C) 4 (D) 5
4.32 The product in the reaction (II) will be
CCH3
O
Cl
CCH3
Cl
OEt
OH
CH C CH3 3
OH
CH2Cl
CH C CH3 3
OH
CH2 CH3
(A) (B) (C) (D)
4.33 In which seft of the reactions in (III) the product will be 2 alcohol ?
(A) a, b, c (B) b,c,d (C) c,d (D) c,d,e
-
7/25/2019 Questions Chapter 1-10
39/107
4.34 Match teh following consider the reaction of CH3MgBr with the compounds in column A andproduct are written in column B.
Column A Column B
(A) CINH2 (p) CH3CN
(B) CICN (q) CH3NH2(C) CH3COCI (r) C2H5COCH3(D) C2H5COOC2H5 (s) CH3COCH3
4.35 Match the following :
O
Cl C
O
C
COOH
O C CH3
CH = CH2
O
(i) [Al(OiPr) ] + CH CH CH3 3 3(ii) H O2 OH
(1)
(2)
(P)
(Q)
NaBH (C H OH + H O)4 2 5 2
Na/EtOH (low temp.)(3) (4) (ii) H O2
(R)(i) LiAlH / Et O4 2
(S)
H C OH
COOH
HOH C2
O
O C CH3
CH = CH2
HC
OH
COOH
Cl C
O
O C CH3
CH = CH2
O
HC
OH
COOH
HOH C2
O
O C CH3
CH = CH2
O
HC
OH
COOH
HOH C2
OH
CH = CH2
O
(X)(P)
(Y)
(Z)
(Q)
(R)
(W)(S)
Column - I Column - II
-
7/25/2019 Questions Chapter 1-10
40/107
4.36 Match the following :Column A Column B
(A) CH3CHCI 3 2Li CH CH CI
Cul? (p) (CH3)2CHCH2CH(CH3)2
(B) (CH3)2CHI 3 2Li (CH )CH Br
Cul ? (q) CH3CH2CH2CH3
(C) CH3CH2C(CH3)2Br 3 2Li CH CH Br
Cul(r) (CH3)3CCH2CH3
(D) (CH3)3CI 3 2Li CH CH Br
Cul(s) CH3CH2C(CH3)2CH2CH3
4.37 Match the following :Process Graph
(A) Fluorination (p)
Potentialenergy
Reaction CO-ordination
A
B
C
(B) Chlorination (q)A B
C
(C) Bromination (r)A
B
C
(D) Iodination (s)
A
B
C
Position(A) is for CH4,X, (B) is for CH3, HX, (C) is for CH3X,X
SECTION - VII : SUBJECTIVE ANSWER TYPE
SHORT SUBJECTIVE :
4.38 An isomer of C5H12 gives total six isomeric products on monkochlorination. Calculate thepercentage yield of the primary monochloride which is chiral. Consider the following relativereactivity of CH bonds for chlorination.
1 3 5
2 C H 3 C H1 C HDegree of C H
Relative reactivityfor chlorination (RR)
-
7/25/2019 Questions Chapter 1-10
41/107
4.39 How many molar equivalent of R-MgX is required in reaciton with formic anhydride completely?
4.40
HS
C NH2 C CH
O
C OH
O
excessCH MgBr3 the numbers of CH gas formed in this reaction4
4.41 Observe the following experiment
Mgpowder
An alkyl halide (P)ethereal solution
(lce)
A sweetsmelling liquid (Q)
H O2
(R)(1) (2)
(I)(II) (III)
(a) If the reactant 'P' is ethl chloride then the product R has the numbers of optically activecompound:
(b) If the loquid Q isH C OC H2 5
O then the product R can be (P can be any other halide)
CH CH CH3 3
OH
(1) CH C CH3 3
OH
(2)CH3
H C C H52
OH
(3)H
C H C C H2 5 2 5
OH
(4)C H2 5
(c) If R is C CH3
CH3
OH
then the numbers of monochlorination product are:
4.42 O
O
O
1 mole CH Mg X3
+ H O2X
The numbers of stereoisomers of 'X' is :
-
7/25/2019 Questions Chapter 1-10
42/107
SECTION - I : STRAIGHT OBJECTIVE TYPE
5.1 The major product of the following reaction would be
NH
Br2
NH
BrBr
N
H Br
N
H Br
N
Br
(A) (B) (C) (D)
5.2 In the following series of reactions the major products P and S are respectively.
Br2 / h (P)tBuO ,
(Q)(i) HOBr/H+
(ii) ThO2,
(iii) alc.KOH,
(R)(i) HOBr/H+
(ii) ThO2,
(iii) alc.KOH,
(S)
(A)Br
;
(C)
Br
;
(B)
Br
;
(D) ;Br
5.3 End product D of the following reaction will be
ClA B C D
H O2 ZnCl HCl2 Mg/ether D O2
D(A) (B) OD (C) D (D) D
OD
5.4 consider the following reactions
H C5 2 C2H5
H
C2H5
HC = C
H C5 2 H
HC = C
C2H5CH2CH C5 2
O2CH
3
CH2
COOH
R1 R2
R3
R4
H C C5 2 CC H2 5
The correct set of reagents for these reactions is
Alkenes & Alkynes
5
-
7/25/2019 Questions Chapter 1-10
43/107
R(A) H /Lindlar catalyst(B) H /Lindlar catalyst(C) (i) O , (ii) H O(D) H O,H SO ,HgSO
1
2
2
3 2
2 2 4 4
RNa / Iiq.NHNa / liq.NHH O,H SO ,HgSOH /Lindlar catalyst
2
3
3
2 2 4 4
2
R(i) O , (ii) H OH O,H SO ,HgSONa / Iiq.NH(i) O , (ii) H O
3
3 2
2 2 4 4
3
3 2
RH O,H SO ,HgSO(I) O , (ii) H OH /Lindlar catalystNa / Iiq.NH
4
2 2 4 4
3 2
2
3
5.5 The major product of the following reaction is :
Br Cl(1)
Na / ether
(2)
Br2 / h C H O2 5 / C H OH,2 5(3)
(A) (B) (C) (D)
5.6 Themost ap0propriatew major product of the followning sequence of reactions would be.
CH CH3 2
H3C
C C
CH3
H
CH C O O H3
O
LiAlD4 H3+
O
Me
Me
D
OH()
Et
H(A)
Me
CH3
DH
H()
Et
D(B)
Me
Me
OH
D()
Et
H(C)
CH3
CH3
DH
OD
CH CH3 2
H(D)
5.7 Compound'P' of the following reaction swequence can be
(P) [C H O ]8 6 3O O
O
H O2
+
COOH
[C H O]8 8 CH COOH2CrO / Acetone / H O3 2
[C H ]16 21B
HOO
BH
C C(A) CH2 C CH(B) C CH(C) (C) CH = CH2
-
7/25/2019 Questions Chapter 1-10
44/107
5.8 The alkene limonene has the following structure,
Which product resutls from the reaction of limonene and 1 molar equivalent chlorine water?
OH
CI(A) OH
CI
(B)
OH
CICI
(C)HO
OH (D)CI
CI
5.9 The end product 'W' in the follownign sequence of reactions is :
CH CH2 3
NBS(X) W
alc. KOH
aq. KOH
Y
Z
Hg(OAc)2NaBH4
(A) Ph CH CH O CH Ph2 2
CH3
( ) Ph CH CH PhC 2 2O CH2
( ) Ph CH B O CH Ph
CH3CH3
(D)
Ph CH CH3
CH = CH2
5.10 Which of the following corrently represents tthe rate of acid-catalysed hydration of followningalkenes.
C = CH CH3
CH3
CH 2= CH C H5 PhCH = CH C H2 5 CH C = CH3 2
CH3
(l) (ll) (lll) (lV)
(A) lll > l > ll > IV (B) lV > lll > l > Il (C) l > lll> lll > IV (D) lV > lll > lll > I
5.11 PhC CPhHOCl/H
+Na/NH3
Ph
Ph
A B ; B is
H
Cl
OH
H
(A) (B)
Ph
Ph
HO
Cl
H
H
(C)
Ph
Ph
H
H
OH
Cl
(D) B and C both
5.12 The most stable conformation of the product of followning reaction
C CHHBr / R O2 2
(1 eqivalent)
HBr / dark
H
Br
Br
HH
Ph(A)
Ph
Br
Br
HH
H(B)
Ph
Br
Br
BrH
H(C)
H
H
H
BrPh
Br(D)
-
7/25/2019 Questions Chapter 1-10
45/107
5.13 In the given reaction,
CH3
(X)
B H , THF2 6 H , NaOH2O2 TSCl tBuO K +
(Y)
The product 'Y' is(A) A positional isomer of X (B) Identical to X(C) Chain isomer of X (D) An oxidation product of X.
5.14 Which of the following compouinds would liberate two moles of methane when treated withmethyl magnesium bromide?
CH CH CH C CH3 2(A)
OH
CH C CH C CH3 3(C)
O
CH3
O
(B)
(D)
CH C CH 3 2 CH OH2
O
OH
COOC H2 5
5.15 The best yiest of product 'X' ca be obtained byt using which one of the foloowing sequence ofreagents and reactants
X = CH C C CH CH (CH )3 3 2
OH
(A) CH C CH3NaNH2 (CH ) CHCHO3 2 H3O
+
(A) CH C CH3NaNH2 (CH ) CHCHO3 2 H3O
+
( ) CH C CB ( 3) CH H C H2CH3I
NaNH2
( ) CH C CC 3 H HC H C C2 3CH3INaNH2
OH
OH
( ) CH C CD ( 3) CH H C H2
CH3ICH3MgI
OH
5.16
H C CH CH3 2 3C
CH3
H CH 3 2C NCH2
H C CH3 3C
CH3
CH3 C Cl
O
X, X isAlCl3
(i)CH 3I
(ii) AgOH,
In the above reaction the product will be
-
7/25/2019 Questions Chapter 1-10
46/107
(A) CH CH CH Cl3 2
COCH3
( ) CH CH CH CB 3 2 CH3
Cl O
( ) CH CH CH C 3 2C CH3
Cl
( ) CH CH CH CB 3 2 CH3
Cl OO
CH3
5.17 Fastest rate of electrophilic addition will take place in
(A) HO CH = CH2
(C)CH3O CH = CH2
(B)ON CH = CH2
(D) CH = CH2
5.18 Which of the following will be the correct product (P) for the given reaction ?
OH
Conc. H PO3 4(P)
OH
(A)
OH
(B) (C) (D)
5.19 CH2 X (major)HBrR O2 2
aq NaOHY (major)
H2SO4/ Z (major)
Identify the correct option
BrCH3
BrCH3
OHCH3
OHCH3 CH3
CH3
CH2
OH
CH3Br
CH3
OH
CH2 CH3
Br
CH3
X Y Z
(A)
(B)
(C)
(D*)
-
7/25/2019 Questions Chapter 1-10
47/107
5.20 X HOOC C CH CH CH CH COOH2 2 2 2
O(i) KMnO4 / H O2 /
(i i) H O3+
X may be
(A)COOH
(B)
COOH
(C)COOH
O
(D)
O
5.21
CH3CH3 CH3
CC = C
H(1) C H CO H6 5 3 ( )2 CH MgBr 3 ( )3 H O/H2
+
Product; Product is :
D CC H(CH ) C3 3 D
OHOH
(A) D CC H(CH ) C3 3 D
OH3OH3
(B) D CC H(CH ) C3 3 D
OH3OH
(C) D CC H(CH ) C3 3 D
OHOH3
(C)
5.22 The final product of the following reaction is
MeHH oCOCH3
Ph
Ph
BrCl/CCl4
BrMe
H Cl
Ph
Ph
(A) ClMe
H Br
Ph
Ph
(B) MeBr
H Cl
Ph
Ph
(C) MeBr
H Br
Ph
Ph
(D)
SECTION - II : MULTIPLE CORRECT ANSWER TYPE
5.23 Which statement is correct about the end product of the following reaction series,
C CHHOCI (excess)
(1) (2)
conc. NaOH,
(A) It is optically inctive hydroxy detone (B) It is a resolvable hydroxy acid(C) It is a nonresolvable aldehyde (D) It is an optically inactive hydroxy acid
5.24 The following synthesis can not be carried out be:
CH = CH2 CH = CH2
I
CI I
(A)CI2(1) (2)
ICI / CH COOH3 ICI / CH COOH3(3)
Zn dust
(4)
(B)HOCI / H
(1) (2)
CI / Fe2(3)
ICI / ZnCI (excess)2
(4)
NaOH,
-
7/25/2019 Questions Chapter 1-10
48/107
(C)
(B)
(1)
HOBr / H
(2)
CI / Fe2(3)
ICI / ZnCl (excess)2(4)
Zn dust, CH COOH3
Br / CH COOH2 3
(1) (2)
CI / Fe2
(3)
ICI / CH COOH (excess)3
(4)
NaNH2
5.25 Bu C CHLiNH2 A
(i) PhCHO
(ii) H O2
BMnO2 C
Compound C of the above reaction can not be :
(A)
CHO
C CBu(B)
CHO
C CBu(C)
CHO
C CBu
(D)
O
C C CBu
5.26 Acetone (CH3COCH3) is the major product in :
I
II
III
CH = C = CH2 2H O3
CH C CH3H SO / HgSO / H O2 4 4 2
CH C CH3BH THF3-
H O / OH2 2
(A) I (B) II (C) III (D) none
SECTION - III : ASSERTION AND REASON TYPE
5.27 Statement-1 :
CH2
CH2
HBr
40CCH3
Br
CH2
MinorMajor
CH2+
CH2Br
MinorMajor 20C CH
3
Br
CH2 CH3+
CH2Br
Statement-2 :
CH2CH2 H
+
CH3
CH2+
Allyliccation
Br
Br
CH3 CH2
CH2CH3
+
Br
major at low tempmajor at of high temp
CH3
CH2
Br
-
7/25/2019 Questions Chapter 1-10
49/107
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
5.28 Statement-1 : Me
MeNBS
Me
Me
Br
+
Me
MeBr
Statement-2 : Me
Me
Br.HBr
Me
Me
Me
Me
Br2
Br
Br2
Me
MeBrMe
Me
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
5.29 Statement-1 : Reduction of but-2-yne by Na/liq. NH3given 'trans' but-2-ene.Statement-2 :It is an example of 'anti' addition.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
5.30 Statement-1 : But-1-ene gives 2-Bromobutane with HBr/PreroxideStatement-2 : The reaction involves formation of more stable free radical and in that respect theaddition is Markovnikof although the product obtained appears as anti Markovbnidof product.
(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
SECTION - IV : TRUE AND FALSE TYPE
5.31 The addition of HBr to butadiene at 80C to give 1, 2-adduct is kinetically controlled while thatat 40C to give 1, 4-adduct is thermodynamically controlled.
5.32 In preparation of terminal alkynes from vicinal dihalides, at least 2 equivalents of sodium amide
must be added per mole of vicinal dihalide.
-
7/25/2019 Questions Chapter 1-10
50/107
SECTION - V : COMPREHENSION TYPE
Comprehension # 1
Demercuration allows Mardownikoffs addtion of H, OH without re arangement. The net result isthe addition of H2O. Answer the following question.
5.33 CH3
CH3
CH3 CH2CH =C i)Hg(OAc) . THF2
ii)CH OH, NaBH NaOH3 4A
HI (Conc.)B, Product B is :
(A) (CH ) CCH CH3 3 3
OH
(B) CH3I (C) CH CH3 2I (D) (CH ) CCH CH3 3 3
I
5.34
CH CH = CH3 2
O
NBr
OA
1) Hg)OAc) , THF2) H O
2
2
3) NaBH , NaOH4B C.
OH
The product 'C' formation from B occurs throuth(A) enol formation (B) SN
1mechanism(C) Neighbouring group particitation (D) SNAR mechanism
5.35
OHi) Hg(OAC) .THF2
ii) NaBH , NaOH4A,
Product 'A' is :
(A)
OH
HO (B) OH (C)
OH
(D)
OH
OH
Comprehension # 2
(A)AI O2 3
250C(B)
HI
(ii) AgOH(C)
AI O2 3
150C(B) (A)
(i) B H2 6
(ii) H O ,OH2 2
In the above reaction sequence (A) and (c)are isomers. MOlecular formula of B is C5H10, which
can also be obtained from the product of the reaction with CH3CH2MgBr and (CH3) CO andfollowed followed by acidification.
5.36 Identify the structure of A(A) CH3CH2CH2CHCH3(B) (CH3)2CHCHOHCH3(C) (CH3)3CCH2OH (D) CH3CH2CHCH2CH3
OH
OH
5.37 Identify th structure of B
(A) (CH ) CHCH=CH3 2 2 (B)
CH3
CH2
CH3
CH3 C C=
(C)(CH ) CH= CHCH3 2 3 (D) CH =CHCHCH2 3CH3
-
7/25/2019 Questions Chapter 1-10
51/107
5.38 Identify the structure of C
OH OHOH
CH3
(A) CH CH CH CHCH (B) CH CH CCH (C) (CH ) CCH OH (D) CH CH CHCH CH3 2 2 3 3 2 3 3 3 2 3 2 2 3
SECTION - VI : MATRUX - MATCH TYPE
5.39 Match the column Iwith column II
Column -(I) Column -(II)
(A) C CDHgSO4
D SO , D O2 4 2
(B)
CH3
*14 H SO2 4
H O2
(C)
CH3
*14 B H /THF2 6
OH /H O2 2
(D) C CDB D /THF2 6
OD /H O2 2
(p)
CH3
OH
CH3
*14
(q)
CH3
CH OH2
*14
H
(r) CD CDO2
(s) C CD3
O
SECTION - VII : SUBJECTIVE ANSWER TYPE
SHORT SUBJECTIVE :
5.40 (a) CH3 CH3
OH OH(X)
CH C C CH
Total no. of stereoisomers of the product when above compound(b) Total no. of stereoisomers of the product when above compound (X) is reduced by lindlar
catalyst.(c) Total no. of stereoisomers of the product when (X) is reduced by Na/liq NH3(Birch reduction)(d) No. of products that we wil kjget when optically inctive form formed in part (B) reacts with
PhCOOH followed by hydrolysis.
5.41 CH3 CH = CH CH3 reacts with Cl2at 500C. Find out total no. of possible products.
-
7/25/2019 Questions Chapter 1-10
52/107
5.42
Et
CHCIBr2
(CH )3 3 COKm no. of products.
5.43CH3 CH3
CH
CH
+ CH N2 2U m Total no. of products.
5.44
CH3 Cold Dil
KMnO4
KMnO4HIO4
NH OH2
(excess) Total no. of isomers (including stereo) are formed in
the products.
-
7/25/2019 Questions Chapter 1-10
53/107
SECTION-I : STRAIGHT OBJECTIVE TYPE
6.1
CH = CH COOH
HOCI / H
The major product is :
(A)
CH = CH COOH
CI
(B)
CH = CH COOH
CI(C)
CH = CH COOH
CI(D)
CH CH COOH
CI
OH
6.2 MeO OH CI
O
O
S MeHCI(1)
Br / Fe
(2)2 H
(3)
+
The major product is
(A) MeO
Br
(B) MeO
Br
OH (C) MeO
Br
(D) MeO
Br
OH
6.3 The product is :
OHO
O
O
||
||
product.
O
O
OH
OH
(A) (B)
O O
O
O O
(C)
O
O
OO
(D) None
6.4
Ph
Me
Me
OH
PhC C
I
AgNO3
Aromatic Compounds
6
-
7/25/2019 Questions Chapter 1-10
54/107
Major product is
(A)Ph
NO3OH
MeC C
PhCH3
(B) Ph
Me
C
Ph
C
O
Me (C) Ph C C Me
PhO
Me
(D) None of these
6.5
CH3
Me CCI3
AICI3
PhCOCI
AICI3
Br / AICI2 3Product is
(A)
Me O
C Ph
(B)
Me O
C PhBr
C(Me)3
(C)
Me O
C Ph
Br
(D)
Me O
C Ph
Br
C(Me)3
6.6 Why does the reaction produce stable salt?
OHCI
A
OHCI+
Because(A) In 'A' the ring is aromatic(B) 6 p electrons are present(C) Ring in a is stabilised by closed loop conjugation(D) All of these
6.7 The major product of reaction
O
C
OMe
O
HNO + H SO3 2 4
O
C O
(A)
NO2
OMe
(B)
O
C O
OMeNO2
(C)
O
C O
OMe
NO2
(D)
O
C O
NO2
OMe
6.8 The end product of the folloowing reaction sequence is:OCH3
+
O
O
O
||Dry. AICI3 Zn Hg / HCI SOCI / Pyridine2
OH (tautomerises)H O2
Dry. AICI3
-
7/25/2019 Questions Chapter 1-10
55/107
(A)
OCH OH3
(B)
OCH3OH
(C)
CH O3 OH
(D)
CH O3
OH
6.9 The end product of following reaction is
CH COCI / AICI3 3(1)
C H COCI / AICI2 5 3(2) (3)
CIO
COO
(A) O = C
C H2 5
(C)
OOC(B) C C H2 5
O
OOC(D) COOCOO
||
OC
C H2 5
6.10 The product of the followiing reactions is
O
C CH3
|| CH C CI3
||O
AICI3
(A) C CH3
||O
OC =
CH3
(B) C CH3
||O
O
C CH3
(C) C CH3
||O
O
H C C3
(D) C CH3
||O
H C C3
O
6.11 Which of the following is best sequence of reagents for the conversion of
Br
CH3
(A)Br / Fe2 conc. H SO2 4 CH CI / AICI3 3 H O3
(B)CH CI / AICI3 3 conc. H SO2 4 Br / Fe2 H O3
(C)CH CI / AICI3 3 3CI /2 h Br / Fe2 Zn / HCI
(D)HNO + conc. H SO3 2 4 CH CI / AICI3 3 Sn / HCI NaNO / HCI2 CuBr
6.12 The intermediate product 'X' of following synthesis is identified as :
CI /FeCI2 3 conc. H SO2 4 Fuming HNO3
'X'
NH3/Cu2O/
120C 100C
dil.H So ,2 4
2, 6-Dinitroaniline
-
7/25/2019 Questions Chapter 1-10
56/107
(A)
HO S3
CI
NO2
(B)
O N2
CI
NO2
SO H3
(C)
SO H3
NO2
CI
O N2(D)
NO2
CIHO S3
SO H3
6.13 The major product of the following reaction sequence will be
OHPhCOCI / Pyridine
(1)
CH COCI/AICI3 3(2) (3)
Zn Hg / HCI /
(4)
Br /Fe2
(A) O CCH CH3 2
OBr
(C) Br O C
O
CH CH2 3
(B) H CCH3 2
Br
O C
O
(D) CH CH3 2
Br
O CH2
6.14 In the following reactions X, Y and Z are respectively :
(x) H /Ni2
NH2
OMe
Br /KOH,2 (Z)
(Y)
NaNH /NH ( )2 3 l
X Y Z
(A)
CH = NOH
OMe
CONH2
OMe
, ,
OMe
CI
(B)
OMe
NO2
,
OMe
CI
,
OMe
CONH2
(C)
MeO
CONH2,
MeO
CN,
MeO
NO2
(D)
CN
OMe
,
COO NH
4
OMe
,
OMe
CI
-
7/25/2019 Questions Chapter 1-10
57/107
6.15
NH2
CH COCI3 ABr + H O2 2 B C
H O3+
C (major product) is
(A)
NH2
Br
(B)
NH2
Br(B)
NH2
Br
(D) none of these
6.16 Which of the following is regenerated at the end of the reaction
p Nitro phenol
(X)
(C H ) SO / NaOH2 5 2 4
(1) (2)
Sn / HCI
(3)
NaNO / HCI2(Y)
C H OH6 5
(4)
(?) HI
(9) CuNO2(8)
NaNO2 NaNO2/ HCI
(7) (6)
Sn / HCI(W)
(5)(Z)
NaOH / C H Br2 5
(A) X (B) Y (C) Z (D) W
6.17 Consider the following reaction sequence
Product is:-
HNO +H SO3 2 4 Sn+HCI NaNO +HCI2
(6H)
Cu (CN) +HCN2 2 H O2 Product
(A)
CH OH2
(B)
CN
OH
(C)
COOH
(D)
NH2CN
6.18 The products R and S are respectively
NO2(X) (W)
KMnO /4 OH / Br / Fe2(R)
(Y)
Sn/HCI
KMnO /4 OH / (Z)Br / Fe2 (S)
(A)
HOOC
HOOC
Brand
HOOC
HOOC
Br
NH2HOOC
HOOC
Br
(B) : R and S are same products
(C)
HOOC
HOOC
NO2
Brand
HOOC
HOOC
Br
(D)
HOOC
HOOC Br
NO2
and
HOOC
HOOC
Br
NO2
-
7/25/2019 Questions Chapter 1-10
58/107
6.19 The end product 'Z' of the reaction sequence is
CI O
CIAICI3
XZn/Hg
Conc. HCIY
Se/Z
(A) (B)
(C) (D) Both A and B
6.20 NO2
Br
KCN/C H OH2 5A
H O3+
C. Product 'C' isNaOH+CaO
distilation
(A)
COONa
Br
(B)
Br
COONa
(C)
NO2
(D) None of these
6.21NH2
NH2HNO2 A B, Product 'B' is
(A)
N CI2+
(B)
N
N
N
H
(C)
N
N
N
H
(D) All of these
-
7/25/2019 Questions Chapter 1-10
59/107
SECTION - II : MULTIPLE CORRECT ANSWER TYPE
6.22B A
NO2(1) Sn/HCI
(2) KMnO4'x'
'y'KMnO4
[O]
'x' and 'y' are respectively :
B A(A)
COOH
COOH
and
COOH
COOH
NO2
A
COOH
COOH
NH2
(B) and B
COOH
COOH
A
COOH
COOH
NH2
(C) and A
COOH
COOH
NO2
(D) B
COOH
COOH
and B
COOH
COOH
6.23 Which of the following electophilic substitution reaction represent correct product.
(A)
NO2
OCH3
Br /FeBr2 3
NO2
OCH3
Br
(B)
O O
Br /FeBr2 3
O O
Br
(C)
COOCH3
OCH3Br /FeBr2 3
Br /FeBr2 3
COOCH3
OCH3
Br
(D) CCH3
O
CCH3
O
Br6.24 Which of the followning reactions give alkylation product:
(A)
(C) + CH COCI3
+
OH
H
AICI3
(B)
(D)
+ H
+ AICI3Me C COCI3
-
7/25/2019 Questions Chapter 1-10
60/107
6.25 The following conversion reafction can be carried out by using reaction sequence/s.
O
OH
O COOH
(A)
(B)
(C)
(D)
Zn / Hg / HCI, Br2 / h KCN H3O+,
NaBH4 AI O ,2 3 O / H O (oxidative)3 2
Heat I2/NaOH, H+
KMnO / OH / heat4
6.26 Which of the following ion will be aromatic in nature?
(A)
N|H
(B)CI
HH (C)
N
(D)
NH
+
H
SECTION - III : ASSERTION AND REASON TYPE
6.27 Statement-1 : Benzene and ethene both give reactions with electrophilic reagents.Statement-2 :Benzene and ethene both have loosely bound electrons, which can be donatedto vacant orbital of the electrophile.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
6.28 Statement-1 :
H
C
(Triphenylmethane)
is less Acidic than (Fluordane)C
H
Statement-2 : coplanar arrangement of three rings in fluordane, allows more extensivedelocalisation in conjugate anion.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation forStatement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
6.29 Statement-1 :Polycylation in benzene does not occur during friedel Craft's acylation.Statement-2 :As the product ketone is much more reactive than starting material.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
6.30 Statement-1 : 3AIBr3 3 2 3 22Ar C(CH ) Br ArBr CH C CH
-
7/25/2019 Questions Chapter 1-10
61/107
but 3AIBr
2 3 2 6 4 2 3ArCH CH Br o,p BrC H CH CH
Statement-2 : In the first case ipso substitution takes place in which Br displaces (CH 3)3C+, a
stable cation but removel of CH3CH2cause large amount of energy.(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.
(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation forStatement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
6.31 Statement-1 :1, 3, 5 trihydroxybenzene reacts with NH2OH togive oximino derivative where as1, 3 dihydraxy benzene do not
Statement-2: Former exist in
||
||
O
OO
which gives
NOH
NOH
NOH
where at later exists in
OH
OH
no substantial keto form is present which can give oximino derivative(A) Statement-1 is True, Statement-2 is True; Statement-2 is acorrect explanation for Statement-1.(B) Statement-1 is True, Statement-2 is True; Statement-2 is NOT a correct explanation for
Statement-1.(C) Satement-1 is True, Statement-2 is False.(D) Statement-1 is False, Statement-2 is True.
SECTION - IV : TRUE AND FALSE TYPE
6.32 The product of reaction
CH OH2
of with conc. H2SO4 is
6.33 The best position for ArSE in pyridine
4
3
2
1N
is 4
SECTION - V : COMPREHENSION TYPEComprehension # 1
COOH
SOCI2 QSolid N O2 5 R
(CH ) CuLi3 2 SFe / H
T(i) NaNO2 / H
(ii) PhOH / OH(U)
6.34 The product U is
(A) C
H
CH3
N = N OH
(B) H C 3
O
C N = N||
OH
(C)
N = N OH
C
O
H C 3(D)
CH CH2 3
N = N OH
-
7/25/2019 Questions Chapter 1-10
62/107
6.35 S on reaction with CI2/ NaOH or on reaction with CI2/ NaOH followed by acidification will not givewhich of the followong
(A)
NO2
COONa(B)
CH COONa2
NO2
(C) CHCI3 (D)COOH
NO2
6.36 T on reaction with NaNO2/HCI followed by reaction with H3PO2will give.
(A)
CH COCH2 3 COCH3
(B)
CH3
(C)
COCH3
(D)
OH
COCH3
Comprehension # 2
The compound C8H9CI (A) on treatments with KCN followed ny hydrolysis gives C9H10O2 (B).Ammonium salt of B on dry distillation yields C. Which reacts with alkaline solution of bromineto gives C8H11N. (D) Another compound E (C8H10O) is obtained by the action of nitrous acid onD. or by the action of aquous potash A. E on oxidation gives F (C8H6O) Which gives the inneranhydride G on heating.
6.37 The compound A is
(A)CH CH CI2 2
(B)
CH CI2
CH3
(C)
CH CI2
CH3
(D)
CH CI2
CH3
6.38 The compound D is reacts with CHCI3+ NaOH gives a compound H. The structrure of H.
(A) (B)CH CH NC2 2
CH3
(C)
CH CN2
CH3
CH NC2
CH3
(D)
CH3
CH NH CH2 3
6.39 The compound A on reaction with AgCN gives.(A) co,pound H. (B) Compound B (C) compound G. (D) compound D
Comprehension # 3
CH CO2
CH CO2
OAICI3
(1)(X)
(C H O )10 12 2C H O10 10 3(2)
Zn(Hg) HCI/
(Y)
SOCI2
(3)
(Z) (C H OCI)10 11
(C H ) + H10 8 2(T) (S) (R)
Pt, heat(7)
(C H )10 10(6)
H SO /2 4 (C H O)10 12(5)
H / Pt2 (C H )10 10O
(W)(4)
AICI3
-
7/25/2019 Questions Chapter 1-10
63/107
6.40 What product will be obtained if 'W' is treated with C 6H5MgBr followed by D3O and then byheating?
(A)
OD
Ph Ph
(C)
(B)
(D)
OD Ph
6.41 What product is obvtained when (X) is heated with conc. H 2SO4
(A) (B) (C) (D)
O O O
O
O
O O O
6.42 What product is obtained when W is heated with KMnO4 / OH.
(A)
(C) (D)
(B)
COOHCOOH
COOHCOOH
O O
O
SECTION - VI : MATRIX - MATCH TYPE
6.43 Match the following
Column - I Column - II
(A)
(B)
(C)
(D)
(p)
(q)
(r)
(s)
Anti aromatic
Aromatic
Non aromatic
G.F = C Hn n
e:
:e
(Non-Planar)
(Planar)
(Planar)
:e
-
7/25/2019 Questions Chapter 1-10
64/107
6.44
NO2
(1)Sn/HCI(2) (CH CO) O3 2
A B C
Br2
HNO3 Dil.
H SO2 4
H SO2 4
H SO2 4
G
(1) CuBr(2)Sn/HCI
(3) NaNO , HSO2 4F E D
H PO3 2 NaNO2
HBF ,4
H
Write the correct combinations
Column-I Column-II
(A) A(p)
Br
Br Br
(B) B(q)
Br
F
Br Br
(C) G
(r)
NHCOCH3
NO2
(D) H
(s)NHCOCH3
-
7/25/2019 Questions Chapter 1-10
65/107
6.45 Match the correct properties of compounds of column I with column II.
(I) (II)
(A)
OCH=CH2
(p) Gives Benzoic acid with hot alkaline KMnO4
(B)
CH=CH2
(q) o/p directing and activating for E
(C)
CHCH3
OH (r) Gives fastest reaction with an electrophile
(D) CH3
O
C(s) Gives an ester on reductive ozonolysis
SECTION - VII : SUBJECTIVE ANSWER TYPE
SHORT SUBJECTIVE:
6.46
NO2
(I) (II) (III) (IV) (V)
OH
(C H ) SO2 5 2 4 Zn/HCI/ NaNO , HCI2 Phenol Br /H O2 2NaOH (4) (5)OH (1)
(2) 5C (3)
The steps involved in the above reaction can be arranged as.Electrophilic substitution = step (w)Nucleophilic substitution=step (x)Reduction reaction = step (y)Diazocoupling reaction = step (z)
Assign the correct numbers to the type of reactions as follows w x y z
6.47 Observe the following reaction sequence
Phenol(1)
(X) (Y) (Z)NaOH (1 eq) HCN, HCI/AICI3 NH NHPh2
Me
D I
H
(3) (4)
(2)
Answer the following questions in the given format :
P Q R S
P = Number of organic products formed in step-1Q = Number of organic products formed in step-2 (singnificant products)
R = Number of organic products formed in step-3 (singnificant products)S = In which step aromatic electrophilic substitutiion has taken place
-
7/25/2019 Questions Chapter 1-10
66/107
6.48 CH CI/AICI3 3