NAME: Instructions: Don’t panic! Read each question ......NAME: Instructions: Don’t panic! Read...
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NAME: Instructions: Don’t panic! Read each question carefully! Partial credit will be awarded when possible, so complete as much as you can even if you cannot finish a question. Place your final answer on the line or in the box if one is provided. Good Luck! Grading Scheme:
Transcript of NAME: Instructions: Don’t panic! Read each question ......NAME: Instructions: Don’t panic! Read...
NAME: Instructions: Don’t panic! Read each question carefully! Partial credit will be awarded when possible, so complete as much as you can even if you cannot finish a question. Place your final answer on the line or in the box if one is provided.
Good Luck! Grading Scheme:
Multiple Choice 1) If benzene is subjected to Friedel-Crafts alkylation, then sulfonation, then halogenation, which of these product would be least likely to form?
B 2) Which of the following are aromatic?
A. 1 and 3 B. 1, 3 and 4 C. 2 and 4 D. 3 and 4 3) Which of the following represents an intermediate in the bromination of phenol?
D 4) Which acyclic compound was used to form this hemiacetal?
D
5) Which of the following would react the fastest with sodium methoxide?
A B
C D
BrCl
OMe
Cl
NO2
I
CH3
C
6) Which of the following reagents are used to carry out chlorination of benzene?
A) Cl2/CCl4 B) Cl2/FeCl3 C) Cl2/AlCl3 D) NaCl/Fe E) both B & C
7) Predict the major product for the following reaction.
(CH3)2CHCH2Cl
AlCl3
CH2CH(CH3)2 CHCH2CH3
CH3
C
CH3
CH3
CH3
I II III
CH2CH2CH2CH3
IV A) I B) II C) III D) IV E) none of these
8)
Which one of the following compounds does not undergo Friedel-Crafts reaction?
A) benzene B) chlorobenzene C) nitrobenzene D) toluene E) t-butylbenzene
9)
Predict the major product for the reaction between benzene and 2-chlorobutane in the presence of AlCl3.
A) chlorobenzene B) sec-butylbenzene C) ethylbenzene D) isopropylbenzene E) t-butylbenzene
10)
Which of the following halides cannot be used for Friedel-Crafts alkylation reaction?
A) bromobenzene B) vinylchloride C) 2-chloropropane D) Chloroethane E) both A & B
11)
Provide the structure(s) of the product in the following reaction sequence
12) A Which of the following reactions would produce isopropylbenzene as the major product? I
ClII
OHIII
H2SO4
IV
AlCl3
Cl
AlCl3 H2SO4
A) I B) II C) III D) IV E) all of these
13) What is the correct structure for 7-methyl-4-octanone?
O
O
O
OI IIIII
IV V
O
A) I B) II C) III D) IV E) V
14) What is the IUPAC name for the following compound?
O
A) 2,4-dimethyl-2-pentenone B) 2,5-dimethylcyclopenten-3-one C) 2,4-dimethylcyclopent-2-enone
D) 3,5-dimethylcyclopent-2-enone E) 2-methyl-5-methylcyclopent-2-enone
15) What is the structure for 5-hydroxy-2-phenyl-3-hexanone?
OH
O
OH
O
OH O
I IIIII
O
OH
IV
H
OH O
V
A) I B) II C) III D) IV E) V
16)
What is the IUPAC name for the following compound?
OBr
A) (S)-2-methyl-2-bromobutanone B) (S)-2-bromo-2-methylcyclobutanone C) (R)-2-bromo-2-methylcyclobutanone D) (S)-1-bromo-1-methyl-2-cyclobutanone E) (R)-1-bromo-1-methyl-2-cyclobutanone
17) Predict the product for the following reaction.
OH
NH
CrO3 Cl
CH2Cl2
I II III
IV
O
O
H
O
OH
Cl
V
HO
A) I B) II C) III D) IV E) V
18)
Predict the product for the following reaction.
OH
CH2OHPCC , excess
CH2Cl2
O
COH
O
O
CH
O
CH
CH
O
O
OH
COH
O
COH
O
COH
OIII
III
IV V A) I B) II C) III D) IV E) V
19) Compound A on ozonolysis yields the following two products What is the structure of compound A? O
H
O
+2. (CH3)2S
1. O3Compound A
H
H
H
I II III IV A) I B) II C) III D) IV E) none of these
20) Predict the product for the following reaction.
H2O / H2SO4
HgSO4
O
OH
HO
C
O
H
OH
HOI II
IV
III
V A) I B) II C) III D) IV E) V
21) Provide the reagents necessary to carry out the following conversion.
O
H
A) 1. H2O/ H2SO4, 2. PCC/CH2Cl2 B) PCC/ CH2Cl2 C) 1. 9-BBN, 2. H2O2/NaOH/H2O D) 1. O3, 2. Zn/acetic acid E) 1. 9-BBN, 2. H2O2/NaOH/H2O, 3. CrO3/H2SO4/H2O
22)
Predict the major product for the following reaction
O
CH3CH2CCl
O
AlCl3
O
O
O
O
O
O
O
Cl
O
I IIIV
III A) I B) II C) III D) IV E) none of these
23)
Predict the product for the following reaction
AlCl3
O
Cl
Cl
Cl
O
O
III
III
O
O
IV V A) I B) II C) III D) IV
E) V
24) Which of the following compounds is most reactive towards nucleophilic addition reaction?
O
H
O
H H
O O O
I II III IV V
A) I B) II C) III D) IV E) V
25)
Rank the following compounds in decreasing order (most to least) of reactivity towards nucleophilic addition reaction.
O
H
O
H H
O O O
I II III IV V
A) I>II>III>IV>V B) II>IV>V>III>I C) III>I>V>IV>II D) I>III>II>IV>V E) V>IV>II>III>I
26)
Which of the following compounds can be classified as an acetal?
O OH O
OH
O O O
I II III IV A) I B) II C) III D) IV E) none of these
27)
Predict the product for the following reaction.
O
CH3CH2OH
H2SO4
excess
HO OH HO OCH2CH3 CH3CH2O OCH2CH3
OCH2CH3
O
I II III IV A) I B) II C) III D) IV E) none of these
28)
Predict the product for the following reaction.
H
O
CH3OH
H2SO4
excess
OH
OH
H
HO OCH3
H
H3CO OCH3
OCH3
O
OH
O
III III
IV V A) I B) II C) III D) IV E) V
29)
Predict the product for the following reaction.
HO
O
H
H2SO4
O
OH
O
OH
O
OH
O
I II III IV V
A) I B) II C) III D) IV E) V
30)
Predict the product when pentanal reacts with CH3NH2 in the presence of an acid catalyst.
H
NCH3
HO
NHCH3
H
NHCH3
H3CHN
O
HO
CH2NH2
I II III
IV V
A) I B) II C) III D) IV E) V
31) Predict the product for the following reaction. O
NH2OH
H2SO4
NH2 HO OHONH2
NOH
I II III IV
NHOH
V
HO
A) I B) II C) III D) IV E) V
32) Predict the product for the following reaction sequence.
CH2CH2OH
PCC (CH3)2NH
H2SO4
N
N
OH
N
N
I IIIV V
N
III
A) I B) II C) III D) IV E) V
33) Predict the product(s) for the following reaction
H3O+
O
O
O
OOH
HO
OH
HO
O
H
OH
HO
H
O
OH
HO
O
OH
HO
I II III
IV V
+ ++
++
A) I B) II C) III D) IV E) V
34)
Predict the product for the following reaction sequence:
H
O
MgBr
H2O
MgBr
H2O
ether
PCC/CH2Cl2
ether
OH O HO
OI II III
IVV
A) I B) II C) III D) IV E) V
35) Predict the product for the following reaction sequence.
Br
CH3CH2CH2CH2Li CH3CCH2CH3
O
Ph3P
ether
OH O
O
I II III
IV V
A) I B) II C) III D) IV E) V
36) Predict the major product for the following reaction.
H2SO4
1. KMnO4/NaOH/H2O
2. H3O+
CH2CH2Cl
AlCl3
excess
C(CH3)3
CH2CH3
C(CH3)3
COH
O
COH
COH
O
O
CH2CH(CH3)2
COH
O
COH
CH2CH3
O
I II III IV V
A) I B) II C) III D) IV E) V
FREE RESPONSE
1) Provide a stepwise curved arrow mechanism for the following reaction.
AlCl3
Cl
THIS IS NOT THE MECHANISM; THIS IS ONLY THE PRODUCT…THE ANSWER WILL BE PROVIDED IN LECTURE
2) Predict the major product for the following reaction and provide a stepwise curved arrow mechanism for the formation of the product.
ClAlCl3+
THIS IS NOT THE MECHANISM; THIS IS ONLY THE PRODUCT…THE ANSWER WILL BE PROVIDED IN LECTURE
3) Provide a synthetic strategy for the following sequence:
NO2
Br
Br
NO2
O
OO
1. iPr-Cl, AlCl32. H2SO4, SO3
3. HNO3
4. dilute H2SO4
5. NBS, heat
1. CH3COCl, AlCl32. Br2, FeBr33. Zn-Hg, HCl
1. CH3COCl, AlCl32. HNO3
(Don't do 2 before 1)
1. Ph3P=CHCH2CH3
2. BH3THF then NaOH, H2O2
3. PCC
4) Complete the following table by filling in the boxes with the appropriate starting material, reagent, or product.
Br2
FeBr3
Mg
thenacetone
CH3Br
AlBr3
HNO3
H2SO4
excess NBS
O
O
O O OOO
OHOO
OH
OH
OH
O
Me
HBr
H2O2
Br
C6H12O
Na2Cr2O7
H2SO4 Me
PPh3
Br OH
O2N
CBr3
O2N
HOCH2CH2OH
cat. H+
LAH
dilute H+
OH O
5) When N,N-dimethylaniline is subjected to bromination conditions, ortho and para products are observed. However, when N,N-dimethylaniline is subjected to nitration conditions, only the meta products are observed. Explain.
Amine – lone pair on N makes it an ortho, para-director Amine with acid gives ammonium ion which is a meta-director 6) Determine the starting material for the synthesis of the following acetals:
O O
O
O
O
OMe
O O
OOH OH
OH
O MeOH
OH
OH O
HH
HO OH
O
or simply...
HO OH
O
7) A student set up a Wittig olefination as shown below. Upon purification, the following spectra were obtained. Mass spectrometry showed the product had a molecular ion peak at 134.2. Was the student successful in the synthesis of the tetra-substituted alkene? Determine the structure of a compound that would provide the following spectra.
The reaction did not proceed as planned. Starting material was recovered: O
