UNIT 4.8 ORGANIC REVISION QUESTIONS 1. Draw all the possible structural isomers of C5H11Br (there are 8 in total).

Label the isomers A H and name them. a) b) c) 2. Identify two molecules which are positional isomers. Identify two molecules which are chain isomers. Identify two molecules which are chiral and draw the two optical isomers of each. Explain briefly how they could be distinguished.

Draw all the possible structural isomers of C5H10 which contain a double bond (there are five in total). Label the isomers A E and name them. a) b) c) d) Identify two molecules which are positional isomers. Identify two molecules which are chain isomers. Identify one molecule which shows stereoisomerism, state the type of stereoisomerism shown and draw and name the two stereoisomers. Draw the structure of a molecule which is a functional isomer of all the molecules A to E. Draw the two possible structures of a molecule with molecular formula C4H8O2 and containing a carboxylic acid group. Name both of the isomers. Draw four possible structures of molecules with the same molecular formula but containing a different functional group. Name the functional group and the molecules containing it. What is the type of isomerism shown between these molecules and the molecules drawn in 3 (a)? Draw the structure of pentan-2-one Draw a positional isomer of pentan-2-one Draw a chain isomer of pentan-2-one Draw a functional isomer of pentan-2-one (not an aldehyde)

3. a) b)

4.

a) b) c) d)

5.

State whether the following preparations will produce a racemate or a single enantiomer: a) b) c) butan-2-ol from but-2-ene butan-2-ol from 2-bromobutane 2-hydroxybutanenitrile from propanal

6.

Name and draw the structures of the organic products obtained by the following reactions. If there is no reaction, state no reaction. a) b) propanal with acidified potassium dichromate propanal with NaBH4

c) d) e) f) g) h) i) 7.

propanone with acidified potassium dichromate propanone with NaBH4 propanone with HCN butanal with Fehlings solution methylpropanal with Tollens reagent butanone with Fehlings solution butanone with HCN

Write equations and give the mechanism for the reaction of butanone with a) b) NaBH4 HCN

8.

Suggest starting materials for the production of the following hydroxynitriles: a) b) c) 2-hydroxybutanenitrile 2-methyl, 2-hydroxybutanenitrile 3-methyl, 2-hydroxybutanenitrile

9.

Write equations for the following reactions: a) b) c) d) e) propanoic acid with sodium hydroxide butanoic acid with sodium carbonate sodium methanoate with hydrochloric acid sodium ethanoate with sulphuric acid 2-methylpropanoic acid with sodium carbonate

10.

Write equations for the following reactions and name any organic products: a) b) c) d) propanoic acid with methanol ethanoic acid with propan-2-ol methanoic acid with propan-1-ol butanoic acid with butan-1-ol

11.

Write equations, using displayed formulae, for the following reactions: a) b) c) d) ethyl methanoate with conc. H2SO4 methyl propanoate with NaOH methylethyl ethanoate with H2SO4 propyl methanoate with NaOH

12.

Write equations for the reaction of the following oil with sodium hydroxide:

H
O

H H H

C C C H

C O

C15H31

C O

C15H31

C15H31

13.

Write equations for the following reactions and name any organic products: a) b) c) d) e) propanoyl chloride with ammonia butanoic anhydride with propan-2-ol methanoyl chloride with aminoethane ethanoic anhydride with 2-aminopropane 2-methylpropanoyl chloride with water

14.

Draw the structures for two possible starting materials for the following products: a) b) c) d) ethyl ethanoate N-methyl propanamide methylethyl propanoate N-ethyl methanamide
Consider the following pair of isomers. O H C O C H 2C H 2C H C (i) Name compound C. ........................................................................................................ (ii) Identify a reagent which could be used in a test-tube reaction to distinguish between C and D. In each case, state what you would observe. Reagent ......................................................................................... .....
3

15.

(a)

O H O C C H 2C H 2C H D
3

Observation with C ......................................................................................... Observation with D.......................................................................................... (4) (b) Consider the following pair of isomers. O H 3C C C H 2C H 2C H E (i) Name compound E. ........................................................................................................
3

O H C C H 2C H 2C H 2C H F
3

(ii)

Identify a reagent which could be used in a test-tube reaction to distinguish between E and F. In each case, state what you would observe. Reagent ......................................................................................... ..... Observation with E ........................................................................................ Observation with F.......................................................................................... (4)

(c)

Draw the structure of the chain isomer of F which shows optical isomerism.

(1) (Total 9 marks)

16. (a)

Butenedioic acid has the formula HOOC-CH=CH-COOH Describe a simple test in each case to show that butenedioic acid is an acid; Test . Result .. (i) unsaturated. Test .. Result .. (4) (b) Draw the structure of the cis-isomer of butenedioic acid and give two reasons which together explain why butenedioic acid shows geometrical isomerism Structure

Reason 1 . Reason 2 . (3) (c) Draw the structure of the organic product formed when butenedioic acid is warmed with an excess of ethanol in the presence of a small amount of concentrated sulphuric acid

(2) (d) Outline a mechanism for the reaction of butenedioic acid with hydrogen bromide.

TOTAL 13 marks

17.

(a)

Outline a mechanism for the reaction of CH3CH2CH2CHO with HCN and name the product. Mechanism

Name of product ......................................................................................................

(5)

(b)

Outline a mechanism for the reaction of CH3OH with CH3CH2COCl and name the organic product. Mechanism

Name of organic product .........................................................................................

(5) (Total 10 marks)

18.

(a)

(i)

Write an equation for the reduction of pentan-2-one by aqueous NaBH4 to form pentan-2-ol Use [H] to represent the reductant. .

(ii)

Name and outline the mechanism for this reaction. Name of mechanism Mechanism

(i)

State why the pentan-2-ol produced in this reaction is not optically active .
(7) (TOTAL 7 marks)

19.

Esters can be hydrolysed by heating with dilute hydrochloric acid to form an alcohol and a carboxylic acid. (a) (i) Name the ester CH3COOCH3 ................................................................................................................... (ii) Write an equation for the hydrolysis of this ester. ................................................................................................................... (iii) Suggest the role of hydrochloric acid in this hydrolysis. ...................................................................................................................
(3)

(c)

State one use of esters other than as a flavouring in foods. ..............................................................................................................................

(1)

(d)

(i)

State how you would find the relative molecular mass of an ester from its mass spectrum. .................................................................................................................. ...................................................................................................................

(ii)

An ester formed by a reaction with butanol has a relative molecular mass of 116. Deduce the molecular formula of this ester. ................................................................................................................. .................................................................................................................. ...................................................................................................................
(3) (Total 12 marks)

20.

The molecular formulae of some compounds that can be prepared trom ethanoic acid are given in the scheme below. C 2H 4O
2

e th a n o ic a c id

e th a n o l/c o n c H 2 S O 4 /h e a t

PC l

C 4 H 8O P (a) (i)

C 2H 3O 2N a Q

C 2H 3O C l R

C 2H 5O N S

Give the name and displayed formula of P. Name.......................................................................................................... Displayed formula

(2)

(ii)

Give the name of the type of reaction which occurs when P is formed from ethanoic acid. ...................................................................................................................
(1)

(b)

Ethanoic acid can be obtained from P. (i) Give the name of the reagent(s) and state the conditions required. ..................................................................................................................

...................................................................................................................
(2)

(ii)

Write a balanced equation for the reaction ...................................................................................................................

(1)

(c)

State the reagent and reaction conditions that could be used for converting ethanoic acid into Q. ................................................................................................................... ...................................................................................................................
(2)

(d)

Give the name and Displayed formula of the amide S. Name........................................................................................................ Displayed formula...................................................................................

(2) (Total 10 marks)

21.

(a)

Name and outline a mechanism for the reaction between propanone and hydrogen cyanide. Name ................................................................................................................... Mechanism

(5)

(b)

Carbonyl compounds can be reduced to alcohols. Write an equation for the reduction of propanone to the corresponding alcohol and identify a suitable reducing agent. In the equation you may use the symbol [H] for the reducing agent. Equation .................................................................................................... ..... Reducing agent ............................................................................................... ..
(2) (Total 7 marks)

22.

(a)

P, Q and R have the molecular formula C6H12 All three are branched-chain molecules and none is cyclic. P can represent a pair of optical isomers. Q can represent a pair of geometrical isomers. R can represent another pair of geometrical isomers different from Q. Draw one possible structure for one of the isomers of each of P, Q and R. Structure of P

Structure of Q

Structure of R

(3)

(b)

Butanone reacts with reagent S to form compound T which exists as a racemic mixture. Dehydration of T forms U, C5H7N, which can represent a pair of geometrical isomers. (i) State the meaning of the term racemic mixture and suggest why such a mixture is formed in this reaction. Racemic mixture ................................................................................................................... Explanation................................................................................................ ................................................................................................................... ................................................................................................................... (ii) Identify reagent S, and draw a displayed formula for each of T and U. Reagent S ..................................................................................................... Compound T

Compound U

(6) (Total 9 marks)

23.

(a)

Terylene is a condensation polymer that can be formed from benzene-1,4dicarboxylic acid and ethane-1,2-diol. Draw displayed formulae to represent: (i) benzene-1,4-dicarboxylic acid;

(1)

(ii)

ethane-1,2-diol;

(1)

(iii)

the polymer Terylene.

(2)

(b)

Give the name of the type of condensation polymer of which Terylene is an example. .............................................................................................................................
(1)

(c)

Outline the difference between the formation of an addition polymer and a condensation polymer. .............................................................................................................................. ..............................................................................................................................

..............................................................................................................................
(2)

(d)

Give the name of one addition polymer. ..............................................................................................................................

(1) (Total 8 marks)

24.

(a)

Draw the structure of each of the three ketones which have the molecular formula C5H10O.
(3)

(b)

Draw the structure of each of the four aldehydes which also have the molecular formula C5H10O. Label with the letter Z the compound which shows optical isomerism.
(5)

(c)

When carbonyl compounds react with HCN, racemic mixtures are often produced. Name the type of mechanism involved and explain what is meant by the term racemic mixture. Choose any carbonyl compound which does not form a racemic mixture when it reacts with HCN and draw the structure of the product formed by the reaction of this carbonyl compound with HCN.
(4)

(d)

Explain why aldehydes react with Tollens (or Fehlings) reagent but ketones do not.
(3) (Total 20 marks)

25.

Simple organic compounds, including structural isomers, can be distinguished from each other by chemical tests, or by spectroscopic methods, or by a combination of both. This question concerns the four compounds whose structural formulae are shown below. CH3(CH2)2CHO A (a) (CH3)2CHCHO B CH3COC2H5 C CH3COOC2H5 D

Draw displayed formulae for A, B, C and D, clearly indicating which is which. Give the names of A, B, C and D.
(8)

(b)

Compound D can be made by a reaction called esterification. State the names of two compounds needed for the reaction and give a condition used in the reaction.
(3)

(c)

Give the name and draw the graphical formula of an isomer of compound D that is not an ester.
(2)

(d)

Describe one chemical test that would distinguish between B and C, and state what you would observe in each case.
(3)

(e)

Compound C reacts with HCN. Give the name of the type of mechanism, and an outline of the mechanism for this reaction.
(5) (Total 21 marks)

ANSWERS TO UNIT 4.8 ORGANIC REVISION QUESTIONS 1.

CH3
CH3 CH2 CH2 CH2 CH2 Br

CH2

CH2

CH Br

CH3

1-bromopentane A
CH3 CH2 CH Br CH2 CH3

2-bromopentane B
CH3 CH2 CH CH3 CH2 Br

3-bromopentane C
Br CH3 CH2 C CH3 CH3

1-bromo,2-methylbutane D
CH3 CH Br CH CH3 CH3

2-bromo,2-methylbutane E
Br CH2 CH2 CH CH3 CH3

2-bromo,3-methylbutane F
CH3 CH3 C CH3 CH2 Br

1-bromo,3-methylbutane G a) b)

bromodimethylpropane H

any two from A, B, C or any two from C, D, E, F two from A, D or G, H or B and E or F

c)

B, D and F are chiral B:

CH3 H Br C CH2 CH2 CH3 CH3 C CH3 CH2 CH2 Br H

and
CH2Br

D:
CH2Br
CH3 C CH3

CH2

C CH3 CH2

H CH3

and
Br C

F:

Br

CH3

CH CH3

H CH3

C CH3

CH CH3

CH3

and

The isomers could be distinguished because they rotate the plane of plane-polarised light in opposite directions. 2.
H H C C H H H C C H

H H C H

H C H

H C

H C

H C H H
H

H C H

H C H

H C H

H C C

H H

C H H

A: pent-2-ene
H H C H H C C H H H C H C H H

B: pent-1-ene
H H C H C H H H H C C

C: 3-methylbut-1-ene
H C H H

D: 2-methylbut-2-ene a) b) c) A and B or two from C, D, E A and D or B and C or E A shows geometrical isomerism

CH3CH2 CH2CH3

E: 2-methylbut-1-ene

CH3CH2

H C C
CH2CH3

C H

C H

cis pent-2-ene

trans pent-2-ene

d)
H H H H C H H H C H C C C H H

3. a)
H H H C H H H H C C C H C OH H O

H H C H

H C H

H C H C

OH

methylpropanoic acid b)
CH3
C O

butanoic acid
O

they are esters

O

CH3 CH2 CH3

CH2

C O

CH3

ethyl ethanoate
O
H

methyl propanoate
O

C O CH

C O

CH3

CH2

CH2

CH3

CH3

propyl methanoate

methylethyl methanoate

They are functional isomers of the carboxylic acids 4. a) pentan-2-one:

H H C H O C H C H H C H H C H H H

b)

positional isomer:
H C H H O C H C H H C H H C H

c)

chain isomer:
H H
C C

d)
H

functional isomer
H HO
C
H
C

O
C

H
C

H C C H

H H

H H

5.

a)

racemate

b)

single enantiomer

c)

racemate

6. a) propanoic acid
H H C H H C H C OH O

b) propan-1-ol
H H C H H C H H C H OH

c) no reaction

d) propan-2-ol
H H C H OH H C H C H H

e) 2-hydroxymethylpropanenitrile
OH CH3

C
CH3

f) butanoic acid

g) methylpropanoic acid
H H C H H H O C OH H C C H

h) no reaction

H H C H

H C

H
O C C OH

i) 2-hydroxy,2-methylbutanenitrile
OH CH3 CH2

C
CH3

7.

a)

CH3CH2COCH3 + 2[H] CH3CH2CH(OH)CH3

O +

O:
CH3 CH2
C

OH

O CH3 CH2

CH3

CH2

C
CH3

+ OH

CH3 CH3

H:

b)

CH3CH2COCH3 + HCN CH3CH2CH(CH3)CN

+
H

+
C

O:

OH

CN

CH3CH2

H+
CH3CH2
CN

CN

CH3

CH3CH2

:CN-

CH3

CH3

8. 9.

a) propanal and HCN

b) butanone and HCN

c) methylpropanal and HCN

a) CH3CH2COOH + NaOH CH3CH2COO-Na+ + H2O b) 2CH3CH2CH2COOH + Na2CO3 2CH3CH2CH2COO-Na+ + CO2 + H2O c) HCOO-Na+ + HCl HCOOH + NaCl

d) 2CH3COO-Na+ + H2SO4 2CH3COOH + Na2SO4 e) 2CH3CH(CH3)COOH + Na2CO3 2CH3CH(CH3)COO-Na+ + CO2 + H2O 10. a) b) c) d) 11. a)
O

CH3CH2COOH + CH3OH == CH3CH2COOCH3 + H2O organic product = methyl propanoate CH3COOH + CH3CH(OH)CH3 == CH3COOCH(CH3)CH3 + H2O organic product = methylethyl ethanoate HCOOH + CH3CH2CH2OH == HCOOCH2CH2CH3 + H2O organic product = propyl methanoate
CH3CH2CH2COOH + CH3CH2CH2CH2OH == CH3CH2CH2COOCH2CH2CH2CH3 + H2O

organic product = butyl butanoate

O

H
b)

C O

+
CH2 CH3

H2O

C OH

CH3

CH2

OH

CH3

CH2

C O

+
CH3

NaOH

CH3

CH2

O Na

+ - +

CH3

OH

c)
OH
O

CH3

O C OH

C O
CH

CH3

H2O

C H

CH3

C
H

CH3

CH3

d)
O

C O

CH2

CH2

CH3

NaOH

+ O- Na

CH3

CH2

CH2

OH

12.
H
O

H H H

C C C H

C O

C15H31

C C C H

OH OH OH

C O

C15H31

+ 3NaOH

H H

Na +O

C15H31

C15H31

13.

a) b)

CH3CH2COCl + NH3 CH3CH2CONH2 + HCl organic product: propanamide

(CH3CH2CH2CO)2O + CH3CH(OH)CH3 CH3CH2CH2COOCH(CH3)CH3 + CH3CH2CH2COOH

c) d) e)

organic products: methylethyl butanoate and butanoic acid HCOCl + CHCHNH HCONHCHCH + HCl organic product: N-ethyl methanamide
(CH3CO)2O + CH3CH(NH2)CH3 CH3CONHCH(CH3)CH3 + CH3COOH

organic products: N-methylethylethanamide and ethanoic acid CH3CH(CH3)COCl + H2O CH3CH(CH)COOH + HCl organic products: methylpropanoic acid

14.

a)
H H C H C Cl O

CH3

CH2

OH

b)
H H C H

O
C
H

C Cl

+
OH

CH3

NH2

c)
O
CH3 CH2

C Cl

CH3

C
H

CH3

d)
O
H

C Cl

CH3

CH2

NH2

15.

(a)

(i)

propyl methanoate (1) not propanyl

A wrong reagent or no reagent scores zero An incomplete reagent such as silver nitrate for Tollens, or potassium dichromate loses the reagent mark, but can get both observation marks penalise observations which just say colour change occurs or only state starting colour
(ii) Reagent: NaHCO3 (1) Observation with C: no reaction (1)

Observation with D: effervescence (1) for C and D NOT Tollens Test an identified (hydrogen) carbonate no reaction bubbles or CO2 acidified K2Cr2O7 goes green no change acidified KMnO4 goes colourless no change correct metal no reaction bubbles or H2 UI or stated indicator no change

4 PCl5

Observation with C observation with D

no reaction (misty) fumes

red or correct colour pH 3 6.9

(b)

(i)

Reagent: pentan-2-one (1) or 2-pentanone but not pent-2-one or pentyl Reagent: Tollens or Fehlings (1) Observation with E: no reaction (1) Observation with F: silver mirror or red ppt (1) for E and F 4

(ii)

Test observation with E observation with F

Tollens no reaction silver or mirror or grey or ppt H

Fehlings or Benedicts no reaction red or ppt not red solution

iodoform or I2/NaOH yellow (ppt) no reaction

acidified K2Cr2O7 no change goes green

Schiffs no reaction goes pink

(c)

3H

C C

H
3H

(1)

must be aldehyde. Allow C2H5 for CH3CH2 otherwise this is the only answer 16(a) (i)

Test Result (ii)

n a m e d c a r b o n a te N a2C O 3 p H /u n iv e rs a l in d ic a to r p H m e te r o r N a H C O 3 r e d /p in k /o ra n g e /y e llo w v a lu e < 7

M g (1 ) H 2 or or C O 2 e ffe rv e s c e n c e e ffe rv e s c e n c e (1 )

Test Result

B r2 d e c o lo u riz e d (b ro m id e C E = 0)

(a c id ) K M nO

(1 )

c o lo u rle s s o r b ro w n (1 )

H O
(b)

H O O C C H C

C O O H H [1 ]

p e n a liz e or

C CO O H C

cannot rotate double bond (1) 2 different groups on each C (1) (c) C2H5 C2H5 CH3CH2OOC CH = CH COOCH2CH3 (2) monoester scores 1 wrong alcohol 0 penalise 3

(sticks) once per paper (1 ) C H H C O O H

H O O C (d)

CH (1 )

C H H B r

CO O H (1 )

H O O C (1 ) .. Br

CH

penalize first mark : if wrong acid (unless if same error as in (b)) or if Br2 4
[13]

17.

(a)

Mechanism

( 1 M ) O ( C
3

O
3

H + : M ( 1 )

4
3 2 2

O C C H

H C N H C

( H N C ( :1 )

2C

( 1 C) N

M 3 M 1 Allow C3H7 if structure shown elsewhere penalise HCN splitting if wrong Name of product: 2-hydroxypenta(ne/o)nitrile (1) or 1-cyanobutan-1-ol (b) Mechanism M 2 ( 1 O) ( C
3

O
3C 2

: C l
3 2

( C

H ) ( 1 ) . . O M H) H

O + C
3H

O C O

H C3

C M M

H 3 4

( C. .

s t r u c( 1 t u) r e 3 a r (r 1o ) w s

Name of organic product: methylpropanoate (1)

5 [10]

18.

(i)

C H

C H 2C H 2C H

O or C5H10O
QoL

+ 2 [H] CH3CH(OH)CH2CH2CH3 (1)

or C5H11OH

(ii)

Name of mechanism: nucleophilic addition (1) Mechanism: (C H 3 ) C (C H 3 C H 2 C H 2) [C

(1 ) O

:H

C H

(1 )
3

H O :

C (1 ) (1 ) or C 3H 7 if s tr u c tu re s h o w n in (i) C H 3CH 2C H
2

O a lo n e lo s e s th is m a r k ]

(iii)

racemic (racemate) mixture formed (1)

OR explained e.g. 2 enantiomers in equal amounts

[7]

16.

(a)

(i) (ii) (iii)

methyl ethanoate (1) CH3COOCH3 + H2O CH3COOH + CH3OH (1) Catalyst (1) 3

(b) (c)

solvents/plasticizers (1) (i) Line with the highest m/z (1) 1

(ii)

C 101

O O C 4H
9

R = 116 101 = 15 CH3COOC4H9 (1) Molecular formula = C6H12O2 (1) 19. (a) (i) (ii) (iii) (b) (c) methyl ethanoate (1) CH3COOCH3 + H2O CH3COOH + CH3OH (1) Catalyst (1)

3
[7]

solvents/plasticizers (1) (i) Line with the highest m/z (1) 1

(ii)

C 101

O O C 4H
9

R = 116 101 = 15 CH3COOC4H9 (1) Molecular formula = C6H12O2 (1)

3
[7]

20.

(a)

(i)

ethyl ethanoate

H H C H C

O H O C H H C H 2 1 H

(1) (ii) (b) (i) esterification / condensation / addition - elimination (1) aqueous / dilute sulphuric / hydrochloric acid (allow HCl(aq); H2SO4(aq) not water) (1) temp. < 100 / warm / heat / reflux (this mark dependent on sensible reagent) (1) 2 (ii) CH3COOC2H5 + H2O CH3COOH + C2H5OH (allow C4H8O2, C2H4O2 but must have C2H5OH) (1) (c) sodium hydroxide / sodium carbonate / sodium hydrogen carbonate (allow formula) (1)

room temperature / aqueous (2nd mark dependent on correct reagent) (1) 2 (d) ethanamide not ethylamide.

H H C H H
(1)

O C N H

2
[10]

21.

(a)

Name

nucleophilic addition (1)

Mechanism (1 ) CH
3

H O : C C N (1 )

(1 ) C H
3

O CH C H
3 3

C (1 ) Equation Reducing agent

N C:

(b)

CH3COCH3 + 2[H] CH3CH(OH)CH3 (1) NaBH4 (1) 2

[7]

CH 22. (a) Structure of P:

C H 2C H C C H

(1) C H
2 3

H Structures of Q and R: CH 3 CH 3 C C CH 2CH H

and
3

C H H

H C C C H (C H 3)2 N O T C 3H
7

(1 )
Q and R in any order

(1 )

(b)

(i)

Racemic mixture: equal mixture of optical isomers / enantiomers

OR in explanation

Explanation: planar ( >C=O) (1) attack from either side is equally likely (1)

(ii)

Reagent S: HCN or (KCN / HCl or H2SO4) (1)

O H C C N
3 2

Compound T: C H 3 C H
C H

C H

(1)

CH CN

Compound U:
H

O
23. (a) (i)

O C C O H
(1) 1

H O

H
(ii)

H C H O H C H H C H n O H allow HOCH2CH2OH (1)

1

C H

O C
(iii)

C O

ester linkage correct ie COOCH2 shown as fully graphical structure (1) rest of molecule correct including
n

(1)

repeat unit may start and finish in different place allow e.c.f. from (a)(ii) (b) (c) polyesters (1) addition: joining together (of monomers with double bond) one product only (1) condensation: also involves the elimination of a small molecule (1) allow specific example e.g. H2O, HCl, CH3OH (d) poly(ethene) / poly(propene) condone missing brackets (1)

2 1

1
[8]

24.

(a)

3 Ketones: C H C H 3C H 2C H 2C C H O
3 3

(1 )

CH

CH

C O

C H

(1 )

C H 3C H 2C C H 2C H O 3

(1 )

(b)

4 aldehydes:

H C H 3C H 2C H 2C H
2

CH (1 ) C H
3

H C H
2

O H

CH CH
3

(1 )

C H 3C H

CH CH
3

(1 )

H C O

C H

C CH
3

(1 )

Y (1 )
(c) nucleophilic

Z (1 )
addition (1)

X (1 )

equal (1) mixture of optical isomers (1) C H 3C H e.g C H 3C H (d)

2 2

O H C C N (1 ) 4

Reagents are oxidizing agents (1) Aldehydes can be (easily) oxidized (1) Ketones are not (easily) oxidized (1) 3
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25.

(a)

H A H C H

H C H

H C H C

H B O (1 ) H

H C H

C H C H

H C O (1 )

H C H C H C O

H C H

H C H H (1 ) D H

H C H C O O

H C H

H C H (1 ) H

A = butanal B = methylpropanal C = butanone D = ethyl ethanoate (1) Ignore numbers in names unless they make them incorrect spellings must be correct accept alternative trivial names correctly spelled (b) ethanol / correct formula (1) ethanoic acid / ethanoyl chloride / ethanoic anhydride / correct formula (1) temperature less than 100 C / reflux heat / concentrated sulphuric acid (1) dilute sulphuric acid / acid conditions / H+ (this mark dependent on sensible answers for first two marks) for ethanoyl chloride, room temperature / dry / anhydrous for ethanoic anhydride, heat / up to 100 C (c) H H C H (1) butanoic acid methylpropanoic acid (1) 2 H C H H C H C O H O or H H C H C H C H
3

3 O C O H (1 )

(d)

heat with Fehlings solution / ammoniacal silver nitrate / Tollens reagent / other suitable oxidising system eg acidified dichromate / Schiffs reagent B gives red, green or brown (precipitate) / silver (mirror) or black/grey (1) precipitate / other, dependent on reagent C shows no change (1) B and C can be referred to as aldehyde and ketone only if names correct in (a) or if there is some other valid identification 3

(e)

nucleophilic addition (1) C H C H 3CH

3

C H C O

O H CN
+

C H CH 3C H (1)

O H C CN

C C N CH 3C H
2

(1 )

(1) for intermediate for product allow ve charge on N but curly arrow must come from C

allow H from HCN or H2O 5

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