Topic 10 Questions KEY

Topic 10 Organic Chemistry ANSWERS 10.1

Functional Groups and Isomerism SL/HL

1.Which of the following pairs represent members of an homologous series? ;

A. C2H4 and C2H6

B. C2H5Cl and C2H4Cl2

C. CH3OCH3 and CH3CH2OH

D. C3H7COOH and C4H9COOH

2. Which names are correct for the following isomers of C6H14?

2-methylpentane

2ethyl-2-methylpropane

2,3-dimethylbutane

A. I only

B. I and II only

C. I and III only

D. I,II and III

3. Which compound is a member of the same homologous series as 1-chloropropane?

A. 1-chloropropene

B. 1-chlorobutane

C. 1-bromopropane

D. 1,1-dichloropropane

4. Which formula represents an amide?A. CH3CH2NH2

B. CH3CH2N(CH3)2

C. H2NCH2CO2H

D. CH3CONH2

5. Which of the following is an amine?

A. CH3CH2NH2

B. CH3CONH2

C. -[CH2CONHCH2CO]n_

D. CH3CH2C ≡ N

6. How many different structural isomers have the formula C4H9C1?

A. 2

B. 3

C. 4

D. 5

7. How many different isomers have the formula C4H10 ?

A. 1

B. 2

C. 3

D. 4

8.

9. The alkanes are a homologous series of saturated hydrocarbons.

(a) State the meaning of each of the following terms.

(i) homologous series [1]

(ii) saturated [1]

(b) (i) State and explain the trend in the boiling points of the first five alkanes. [2]

(ii) Give the structural formulas for the isomers of molecular formula C4 H10 and state the name of each one [2]

Have a general formula

Contain only C-C single bonds

Increases Increase in mass leads to greater Van De Waal forces

CH3CH2CH2CH3 = Butane

CH3CH(CH3)CH3 = 2-methyl propane

10. (i) List three characteristics of an homologous series, and explain the term functional group. [3]

(ii) Draw the four structures of alcohols of formula C4H9OH. Name each one and label them as either primary, secondary or tertiary alcohols. [4]

(iii) Many organic compounds can exist as isomers. Draw and name an isomer of ethanoic acid,

[2]

General formula/differ by CH2 grp/gradual change in phys props/similar chem. Props (any 2)

Func grp = atom or grps of atom responsible for chem. Props of homologeous series (reactive part of molecule)

CH3CH2CH2CH2OH = butan-1-ol = primary

CH3CH(CH3)CH2OH = 2-methyl propan-1-ol = primary

CH3CH(OH)CH2CH3 = butan-2-ol = secondary

CH3C(CH3)(OH)CH3 = 2-methyl propan-2-ol = tertiary

HCOOCH3 = methyl methanoate

Topic 10 Organic Chemistry 10.2

Physical Properties of Organic Compounds SL/HL

1. When the compounds below are listed in order of decreasing boiling point (highest to lowest) what is the correct order?

1. ethane

A. 4,3,1,2

B. 4,3,2,1

C. 3,4,1,2

D. 2,1,3,4

2. fluoroethane 3. ethanol 4. ethanoic acid

2. Which of the following is expected to be a gas at 25° C?

3. Which compound is the most soluble in water?

A. Methane

B Propane

C. Propan-1-ol

D. Pentan-1-ol

4. Statement (S): Solubility of alcohols in water decreases with increase in Mr.

Explanation (E): The relative proportion of the hydrocarbon part in alcohol increases with increasing Mr.

A. Both S and E are true.

B. Both S and E are false.

C. S is true but E is false.

D. S is false but E is true.

5. Explain why the boiling points of ethanol and ethanoic acid are considerably higher than the boiling point of ethanal.

[3]

6. Discuss the factors which affect the boiling points of covalently bonded compounds by reference to the following pairs of organic substances, whose boiling points are given:

• ethane (184 K) and butane (273 K);• ethane ( 184 K) and bromoethane (311 K);• bromoethane (311 K) and ethanol (352 K). [6]

Ethanol and ethanoic acid both contain H bondsSince H is attached to electroneg O atom.Ethanal has only dipole forces due to C=O

Greater van de waals forces in butane Caused by larger Mr increases bp.

Dipole forces in bromobutane Due to polarity of C-Br bond….these are stronger than Van De Waals…higher bp.

Ethanol contains H bonds Due to O-H bond….these are stronger than dipole…higher bp.


Reactions of Alkanes and Alkenes SL/HL

1. Which statement is correct about the reaction between methane and chlorine?

A. It involves heterolytic fission and ions. Cl−

B. It involves heterolytic fission and Cl* radicals.

C. It involves homolytic fission and ions. Cl−

D. It involves homolytic fission and Cl * radicals.

2. Which are characteristics typical of a free radical?

I. It has a lone pair of electrons.II. It can be formed by the homolytic fission of a covalent bond.III. It is uncharged.

A. I and II only

B. I and III only

C. II and III only

D. I, II and III

3. Which is the best description of the following reaction?

C2H4 + H2O → C2H5OH

A. Addition

B. Condensation

C. Dehydration

D. Hydrogenation

4. Which chemical is most likely to be a starting material for a common polymer?

A. CH3CH2CH3

B. CH3CH2OH

C. CH3CHCH2

D.

5. What will be formed when CH2 = CH2 reacts with Br2 in the dark?

A. CH2Br —CH2Br

B. CH3—CHBr2

C. CH2=CHBr + HBr

D. CHBr = CHBr + H2

6. (a) Describe a chemical test to distinguish between alkanes and alkenes, giving the result in each case. [2]

(b) Name the type of polymerization reaction which C3H6 undergoes and draw the structure of a section of the polymer chain formed from three monomer molecules.

[3]

7. Give an equation for the complete combustion of methane, CH 4. Identify two products formed by the incomplete combustion of methane and identify one harmful effect caused by one of the products.

[4]

8. The plastic PVC, poly(chloroethene), is made from the monomer chloroethene, C2H3C1, by a

Bromine waterAlkanes = stays orange….alkenes = turns clear

Addition polymerization-(CH(CH3)CH2 ) --(CH(CH3)CH2 ) --(CH(CH3)CH2 ) - (2 marks)

CH4 + 2 O2 = CO2 + 2 H2OCarbon monoxide (poisonous/internal suffocation)Carbon (respiratory problems/asthma/bronchitis)

polymerization reaction.

(i) Draw the structural formula of chloroethene. [1]

(ii) State the type of polymerization reaction that occurs to make poly(chloroethene) and

identify the structural feature needed in the monomer. [2]

(iii) Draw the structure of the repeating unit of poly (chloroethene). [1]

(iv) Explain why monomers are often gases or volatile liquids, whereas polymers are solids. [2]

9. Alkanes are often described as having low reactivity, although they do react with halogens.

(i) Explain why alkanes are unreactive. [2]

(ii) The first step in the reaction of propane with bromine can be represented by the equation.

Br2→ 2Br∙

State the type of species formed in this step and name the type of bond fission. [2]

10. Under certain conditions ethene can be converted to ethanol.

(i) Give a chemical test to identify ethene and state what would be observed.

(ii) Give a balanced equation for the reaction to form ethanol from ethene.

(iii) State the conditions necessary for the reaction in (ii). [4]

CHCl = CH2

Addition polymersC=C (unsaturated)

-( CHClCH2 )-

Monomers are small molecules…low Mr…weak Van de waal forces..low bpPolymers are v large molecules…high Mr…stronger Van De Waals..high bp

Non polarStrong C-C and C-H bonds

Free radicalHemolytic fission

Bromine waterOrange to clear

CH2 = CH2 + H2O = CH3CH2OH

Heat + (almost conc) sulfuric acid (as a catalyst)


Reactions of Alcohols SL/HL

1. Which compound is converted to butanal by acidified potassium dichromate(VI) solution?

A. butan-1-ol

B. butan-2-ol

C. butanone

D. butanoic acid

2. What is the final product formed when ethanol, CH3CH2OH is reacted with acidified potassium dichromate(VI)?

A. ethanal

B. ethane

C. ethanoic acid

D. ethene

3. Which compound will undergo oxidation when treated with acidified potassium dichromate(VI)?

A. CH3CH2CHO

B. CH3COCH3

C. CH3COOH

D. (CH3)3COH

4. (a) Propan-1-ol, in the presence of a small amount of oxidising agent, forms compound X, and when refluxed with an excess of oxidising agent, forms compound Y.

(i) Identify a suitable oxidising agent and state the colour change. [2]

(ii) Draw the structural formulas of both compound X and compound Y. [2]

(b) Some alcohols are oxidized by heating with acidified potassium dichromate(VI). If oxidation does occur, identify the possible oxidation products formed by each of the alcohols below. Indicate if no oxidation occurs.

Butan–1–ol

Butan–2–ol

2–methylpropan–2–ol

[4]

5. This question is concerned with compounds having the molecular formula C3H8O.

(a)Draw the full structural formulas of the three possible isomers and give the name of each. [5]

(b) Predict how each of these isomers would behave when reacted with limited (i.e. not inexcess) acidified potassium dichromate(VI) solution and describe any observation thatcould be made. Write the structures of any organic products formed and give their names. [6]

Cr2O72- / H+ Orange to (dirty) green

X = CH3CH2CHO Y = CH3CH2COOH

Butanal and then butanoic acid

Butanone

No oxidation (tertiary alcohol)

CH3CH2CH2OH = propan-1-ol

CH3CH(OH)CH3 = Propan-2-ol

CH3-O-CH2CH3 = methoxy ethane (extension)

Propan-1-ol = propanal CH3CH2CHO

Propan-2-ol = propanone CH3C=OCH3

Observations =orange to dirty green.

Methoxy methane = no reaction.


Reactions of Halogenoalkanes SL/HL

1. The reaction between 1-bromopropane and warm dilute sodium hydroxide solution is described as an SN 2 nucleophilic substitution reaction.(i) Explain each of the terms in SN 2. [3](ii) Write an equation and a mechanism for the reaction. [5]

2. (i) 1-bromopropane is described as a primary halogenoalkane and 2-bromopropane isdescribed as a secondary halogenoalkane. Explain these terms with reference to thetwo examples given. [2]

(ii) Give the structural formula of a tertiary halogenoalkane.

[1]

(iii) State the type of substitution reaction undergone by tertiary halogenoalkanes. [1]

3. Give the structural formulas of the four isomers of molecular formula C4H9Cl. State thename of each one and classify it as primary, secondary, or tertiary.

[8](b) Each of the isomers reacts with aqueous sodium hydroxide. State what class of compound isproduced by this reaction.

[1](c) (i) Identify the type of isomer (primary, secondary or tertiary) which will react withaqueous sodium hydroxide almost exclusively by an SN1 mechanism. State the meaning of the symbols in the term SN1 mechanism.

Substitution, nucleophilic, second order

CH3CH2CH2Br + NaOH = CH3CH2CH2OH + NaBr

Polarity of C-Br bond curly arrow from OH- nucleophile

Correct activated complex formed Curly arrow from Br- leaving group

Primary = 1 carbon group attached to functional groupSecondary = two carbon groups attached to functional group

CH3C(CH3)2Br

SN1

CH3CH2CH2CH2Cl = 1-chlorobutane = primary

CH3CH(Cl)CH2CH3 = 2-chlorobutane = secondary

CH3CH(CH3)CH2Cl = 2-methyl 1-chloropropane = primary

CH3C(CH3)2Cl = 2-methyl 2-chloropropane = tertiary

alcohols

TertiarySub, nucleophilic 1st order reaction


Reaction Pathways SL/HL

1. This question refers to the compounds in the following reaction scheme.

C3H7Br Na0H C3H8O 0xidation C3H6O 0xidation C3H6O2

A B C D

(a) State a suitable reagent for the oxidation of B to C and C to D. Explain how the oxidation of B to C could be achieved without further oxidation to D. [3]

(b) The conversion of A to B takes place by an SN 2 mechanism. State what is meant by the term SN2 and describe, by using "curly arrows" to show the movement of electron pairs, the mechanism of this conversion. [6]

2. This question is about four compounds A, B, C and D, which can be made from ethene by the following reactions. All four compounds are liquid at room temperature, and each compound's molecular formula is shown.

C2H4 C2H5O C2H4O C2H5O2

A B C D

(a) Use the information above to identify each of the compounds A, B, C and D giving the name and structural formula of each one. [8]

(b) State the type of reaction occurring when A is converted to B and state the reagent required.

[2](c) Compound A can react with bromine. Write an equation for this reaction andname the product. State a visible change which accompanies the reaction.

[3]

→ →→

Acidified/H+ potassium dichromate product must be distilled off before further oxidation

Sub, nucleophilic, 2nd order (1 mark)

Polarity of C-Br bond Curly arrow showing C-Br bond breaking slowest step is first step

Forrnation of correct carbocation Curly arrow showing attack of OH- on cation

A = Ethene = CH2CH2 B= Ethanol = CH3CH2OH

C= Ethanal = CH3CH2CHO D = Ethanoic acid = CH3CH2COOH

Addition reagent = H2O (and a sulfuric acid catalyst)

CH2CH2 + Br2 = CH2BrCH2Br 1,2-dibromoethane

Orange to clear


Nucleophillic Substitution HL ONLY

1. The alkaline hydrolysis of primary halogenoalkanes usually follows an SN 2 mechanism. For which compound would the rate of hydrolysis be fastest?

A. CH3CH2CH2F

B. CH3CH2CH2C1

C. CH3CH2CH2Br

D. CH3CH2CH2I

2. Which compound reacts most rapidly by a SN1 mechanism?

A. (CH3)3CC1

B. CH3CH2CH2CH2Br

C. (CH3)3CBr

D. CH3CH2CH2CH2C1

3. What is the major product when an halogenoalkane is reacted with a large excess of ammonia?

A. An amine

B. An amide

C. An amino acid

D. An alkene

4. Which one of the chloroalkanes below will hydrolyse most rapidly?

A. CH3CH2CH2CH2C1

5. Which molecule does not act as a nucleophile in a reaction with a halogenoalkane?

A. Ethane

B. Ethanol

C. Ethylamine

D. Water

6. (i) Draw the structure of the four structural isomers of C4H9Cl.

[2]

.

(ii) Identify one isomer in (iii) that undergoes a substitution reaction mainly by an SN1 mechanism.

[1]

CH3CH2CH2CH2Cl CH3CH(Cl)CH2CH3

CH3CH(CH3)CH2Cl CH3C(CH3)(Cl)CH3 tertiary

Tertiary one

(iii) Write the mechanism for the reaction that occurs when the isomer identified in (ii) is warmed with aqueous sodium hydroxide. Use curly arrows to present the movement of electron pairs.

[3]

7. (a) (i) Draw the structures of 2-chloropropanoic acid and 2-hydroxypropanoic acid. [2]

(ii) 2-chloropropanoic acid can be converted to 2-hydroxypropanoic acid by nucleophilicsubstitution. Define the term nucleophile and state the nucleophile required for thisreaction. [2]

(b) Deduce how the rate of reaction of CH2CH2CH2Br with NaOH would compare with that of the compound CH2CH2CH2Cl with NaOH. Explain your answer by referring to the Data Booklet.

[2]

Polarity of C-Br bond Curly arrow showing C-Br bond breaking slowest step is first step

Forrnation of correct carbocation Curly arrow showing attack of OH- on cation

CH3CH(Cl)COOH CH3CH(OH)COOH

Nucleophile = electron rich species/non bonded e pair/attracted to positive species

Warm dilute NaOH

Bromo is fasterData booklet shows that strength of C-Br bond is weaker (since less polar) and so can be broken more easily.


Condensation Reactions HL ONLY

1. What is the name of the compound CH3CH2CH2COOCH3 ?

A. Butyl methanoate

B. Methyl butanoate

C. Methyl propanoate

D. Pentanone

2.

From which two chemicals could this compound be synthesised?

A. butanoic acid and pentan-1-ol

B. butanoic acid and butan-1-ol

C. butanal and pentan-1-ol

D. pentanoic acid and butan-1-ol

3. CH3OH + CH3CH2COOH → CH3CH2COOCH3 + H2O

The forward reaction represented by the equation above is

A. addition.

B. esterification.

C. hydrolysis.

D. neutralisation.

4. Consider the following reaction:heat

CH3COOH + NH3→ CH3COONH4 → CH3CONH2

What will be the final product if aminoethane (ethylamine) is used instead of NH3 ?

A. CH3CONHCH2CH3

B. CH3CONHCH3

C. CH3CONH 2

D. CH3CONH2CH2CH3

5. When ethanol is warmed with ethanoic acid in the presence of an acid catalyst a new product is formed.

(a) Write the balanced equation for the reaction that takes place using the structuralformulas of the organic reactants and products. [3]

(b) State how the organic product may be distinguished from the reactants and to whichhomologous series it belongs. [2]

(c) State two reasons why concentrated sulfuric acid is used. [2]

(d) State and explain how the solubility of the product in water compares with thesolubililty of the two reactants in water. [2]

6. (i) Draw the structural formula of methyl methanoate. State the conditions and the startingmaterials for the preparation of methyl methanoate in the laboratory. Write a balancedchemical equation for the reaction.5]

(ii) Draw the structural formula of an isomer of methyl methanoate. State two physicalproperties and one chemical property that would be different for the two compounds.State how each of these properties differ for the two compounds.

[5]

CH3CH2OH + CH3COOH CH3COOCH2CH3 + H2O

1 mar for products and reactants….1 mark for eq sign

Ester has low bp/volatile…has strong smell.

As a catalyst shifts eq to RHS (as increase acidity on LHS)

Less solubleEsters have no H bonding

HCOOCH3 materials = methanol and methanoic acidConditions = heat + acid (sulfuric) catalystCH3OH + HCOOH HCOOCH3 + H2O

Isomer = CH3COOHPhysical = solubility in water/boiling point/volatilityEsters cannot H bond but carboxylic acids canChemical = AcidityCarboxylic acids will react with carbonates/metals….esters won t.

7. Hexanedioic acid and 1,6-diaminohexane react together to form a synthetic polymer. There are many natural polymers, some of the most familiar being proteins formed from 2-amino acids.

(i) Give the structural formula of each monomer in the synthetic polymer. [2]

(ii) State the type of polymerization reaction that occurs between these two monomers and identify the structural feature needed in the monomers. [2]

(iii) Draw the structure of and state the type of linkage formed in this polymer, and identify the other product of this polymerization reaction. [3]

8. (a) Given the structures of the repeating units of the polymers below, identify the monomers from which they are formed.

[4]

-( CH2-CH2 )-

-( CO-CH(CH3) NH )-

-( NH-(CH2)6-CO-NH-(CH2)4-CO )-

(b) Describe the essential differences between the structures of monomers that form addition polymers and the structures of monomers that form condensation polymers.

[2]

NH2(CH3)6NH2 HOOC (CH3)4 COOH

Condensation polymer 2 functional groups per molecule

Amide link (-C=O – NH -) other product = water

CH2=CH2

HOOC-CH(CH3)-NH2

NH2(CH3)6NH2 and HOOC (CH3)4 COOH(2 marks)

Addition = C=C Condensation = C=O group + nucleophile (NH3,OH- CN- etc)


Stereoisomerism HL ONLY

1. Which molecule possesses a chiral centre?

A. NH2CH2COOH

B. CH3CH(NH2)COOH

C. CH3C(NH2)2COOH

D. (CH3)2C(NH2)COOH

2. Which compound is optically active?

A. CH3COCH(CH3)2

B. (CH3)3CCHO

C. CH3CH2COCH2CH3

D. CH3CH2CH(CH3)CHO

3. Which one of the following compounds is optically active?

A. CH3CH2CH2CH2NH2

B. CH3CH2CHCH3

NH

C. CH3CH2NCH2CH3

H

D. CH3CH2NCH3

CH3

4. W has the structure

(i) Give the structure of the geometrical isomer of W.

(ii) Explain why W has a geometrical isomer.

(iii) Draw two structures for CH3CH2CH(Cl)CH3, showing the relationship between them. [2]

5. There are geometrical isomers of the cyclic compound C4H6Cl2 Draw the structuralformula of two isomers and explain why these two isomers exist.

[3](b) (i) Draw the structural formulas of two isomers of but-2-ene-1,4-dioic acid.

[2] 6. (a) Consider the following compounds:

1-chloropentane, 2-chloropentane, 3-chloropentane

(i) Identify the compound which exhibits optical isomerism and draw the structures ofthe two isomers.

[3](ii) Describe how these two isomers can be distinguished experimentally.

[1]

CH3 H C=C H CH2CH3

No rotation of C=C bond

Mirror images of enantiomers drawn in 3D…(2 marks)

3 D drawing of cis and trans cyclic isomers

Restricted rotation in ring structures

drawing of cis and trans cyclic isomers

2-chloropentane

Mirror images of enantiomers drawn in 3D…(2 marks)

Rotation/effect on plane polarized light.

7. (a) Draw the structures of the two geometrical (cis/trans) isomers of C4H8 , giving their full names. [4]

(b) There are four isomers with the formula C5 H10 which contain a three-membered carbonring. Draw these isomers and label them A, B, C and D.

[2](ii) Indicate, by writing two letters (chosen from A, B, C and D) a pair of isomers that arestructural isomers and a pair that are geometrical isomers. [2]

Structural isomers:

Geometrical isomers:

(iii) From the four isomers A, B, C and D, draw the structure of an isomer that showsoptical isomerism and mark the chiral centre with an asterisk (*). [1]

(c) Use the examples from parts (a) and (b) to explain the existence of geometrical isomers. [1]

8. (a) Explain the term plane-polarized light and describe how the optical isomers of CH3CH2CHClCH3 could be distinguished using a polarimeter.

[2](b) Explain why a sample of CH3CH2CHClCH3 produced did not show optical activity.

[1](c) 2-chloropropanoic acid and 2-hydroxypropanoic acid can both show optical activity.Identify the feature which both molecules possess that accounts for this property.When 2-hydroxypropanoic acid is formed from 2-chloropropanoic acid, the productshows no optical activity. Deduce the type of nucleophilic substitution that takes placeand explain your answer. [4]

drawing of cis and trans cyclic isomers… 2 marks

correctly labeled as cis but-2-ene and trans but-2-ene

3 D drawing of cyclic isomers…. 2 marks

Chain isomers 2 x CH3 on same C’s..or CH3CH2 (2 marks)

Cis and trans isomers …2 x CH3 groups on different C’s….(2 marks)

Either of the geometric isomers

Restricted rotation of a ring structure

Light vibrating in one plane One isomer rotates it to left, other to right

Racemic mixture

SN1Formation of carbocation intermediate is planar by SN1 mechanismNucleophile can then attack with equal chance on either side of cation.Equal chance of both optical isomers being formed = racemic mixture.


Reaction Pathways HL ONLY

1. This question is about four compounds A, B, C and D. B, C and D can be made from A by the following reactions. A, B and C are liquid at room temperature, and each compound's molecular formula is shown.

Sodium was added to each liquid compound. Gas bubbles formed slowly in A but rapidly in C.

(a) Use the information above to identify each of the compounds A, B, C and D, giving thename and structural formula of each one. [4]

(b) (i) State the type of reaction occurring when A is converted to B and C, and state asuitable reagent and conditions for the reaction. [3]

(ii) Explain why B is much harder to obtain than C in this reaction. [1]

(c) Identify the gas formed when A and C react with sodium and write an equation for the reaction of C. Name the other product of the reaction between sodium and C. [4]

(d) Arrange the compounds A, B and C in increasing order of boiling point (lowest boiling pointfirst). Explain your choice. [4]

(e) None of the compounds A, B, C and D exist as optical isomers. State the structural featurewhich is present in a compound that exists as optical isomers. Draw the structural formula ofthe isomer of A that exists as optical isomers, [2]

a) A = butanol = CH3CH2CH2CH2OHB= Butanal = CH3CH2CH2CHOC = butanoic acid = CH3CH2CH2COOHD = But-1-ene = CH2=CHCH2CH3

b) i) oxidation K2Cr2O7 Acid and heat

ii) Hard to stop complete oxidation…need to distil product B away from ox agent.

c) H2 gas product = sodium butanoate

2 Na = 2 CH3CH2CH2COOH = 2 CH3CH2CH2COONa + H2 (2 marks)

d) butanal….butanol….butanoic acidbutanol = dipole (weaker intermolecular force)Butanol = H- bonds (stronger intermolecular force)Butanoic acid = stronger H-bonds + dipole

e) asymmetric carbon/4 different grps attachedCH3CH(OH)CH2CH3

2. Compound A is a bromoalkane. When compound A reacts with warmdilute sodium hydroxide solution an organic compound B is formed which has a relative molar mass of 74.12 and contains 64.81 % carbon, 13.60 % hydrogen and 21.59 % oxygen by mass. Compound B can be oxidised by an acidified solution of potassium dichromate(VI) to give compound C which contains the same number of carbon atoms as compound B.

(a) (i) Calculate the empirical and molecular formula of compound B. [3 mark]

(ii) Give four different possible structural formulas for isomers ofcompound B which are consistent with the information that it hasbeen formed from the reaction of a bromoalkane with NaOH (aq). [4 marks]

(iii) Which of the four isomers given in (ii) above is not consistentwith the fact that compound B can be oxidised by an acidifiedsolution of K2Cr2O7 to give compound C? Explain your answer. [2 marks]

(iv) Give the structures of the organic products which would beformed when the remaining three structural isomers of compoundB are fully oxidised by acidified K2Cr2O7. [3 marks]

(b) It is shown that compound B exhibits optical activity.

(i) Explain what is meant by optical activity and show clearly the twooptical isomers of compound B. [4 marks]

(ii) Give the structural formulas and names of compound A andcompound C. [4 marks]

(iii) Name the mechanism which describes the reaction betweencompound A and dilute sodium hydroxide solution. [1 mark]

(iv) Give the balanced equation for the reaction of compound B withethanoic acid in the presence of sulfuric acid and name thefunctional group present in the organic product [3 marks]

Topic 10 Questions KEY

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