SERANGOON JUNIOR COLLEGE

H2 9647 CHEMISTRY
2014 JC2

Carbonyl Compounds
Tutorial 7

Compulsory Questions
[To be discussed during tutorial. Do all questions on foolscap paper. Show all
relevant workings.]
Fill in the structural formulae of the organic compounds A D, and state the reagents
and conditions for steps I V.

C9H10O3
K2Cr2O7 /H
heat

Tollens
reagent

No silver mirror
2,4-DNPH

Orange ppt

II
IV
III

+ CHI3
Tollens
reagent

Silver
mirror

Fehlings
solution

No ppt

9647 H2 Chemistry

Page 1 of 25

Step
I
II
III

Reagents and conditions

LiAlH4 in dry ether, r.t.p.
(H2 in Ni catalyst or NaBH4 cannot not be used)
K2Cr2O7, H2SO4(aq), heat with distillation
1. I2 (aq), NaOH(aq), warm
2. HCl(aq)

IV

HCN, NaCN (aq), 10-20oC, cold

HCl(aq), heat

9647 H2 Chemistry

Page 2 of 25

2(a)

Name and describe the mechanism of the reaction between ethanal and
hydrogen cyanide, stating and explaining the use of any other reagents
required for the reaction. Show clearly the structural formulae of any
intermediates, as well as of the products.
Mechanism: nucleophilic addition
Other reagent required: Trace amount of NaOH
Step 1 :
O -

O:
slow

C +

H
:CN

CH3

CH

CN

Step 2 :

O:
CH3 C

CN

CN

OH
CH3 C

CN

:CN

The slow (rate-determining) step involves the CN- nucleophile.

However HCN is a very weak acid which dissociates partially to give
small amount of CN-, i.e.
HCN

H+

:CN -- (1)

The trace NaOH will neutralise the H+, causing [H+] to decrease.

By Le Chateliers Principle, the equilibrium position (1) would shift right to

increase the [H+], which hence leads to increase in the [CN-] and rate of
the reaction.
The reaction is thus said to be base-catalysed.

9647 H2 Chemistry

Page 3 of 25

(ii)

The above reaction produces two isomeric products in equal amounts.

Name the type of isomerism that occurs and draw displayed formulae to
illustrate it.
The isomerism that occurs is known as optical isomerism since the
product contains a chiral carbon centre.
H
H
H

H
O

H
N

(iii)

Explain why the products are formed in equal amounts.

A chiral C atom is obtained from the nucleophilic addition then there
would be a racemic mixture formed due to the equal probability of the
nucleophile attacking the carbonyl C atom from from the top and the
bottom as the compound takes a trigonal planer shape.
FYI:
Attack from the top

O-

O:CN-

C
R'
Attack from the bottom

9647 H2 Chemistry

(50%)

and
CN

C
NC

R'
R

(50%)

Page 4 of 25

Starting from a suitable carbonyl compound of your choice, and using a cyanohydrin
as an intermediate, devise a 3-stage synthesis of compound C

.
CH3C(OH)(CH3)CO2CH2CH3
C
Suggest reagents and conditions for each step, and draw the structural formula of
every intermediate compound.

CH3 O

C O

CH3

C O CH2CH3

OH

Analysis:

Main functional groups in A : alcohol, ester

CH3 O
CH3

If final product contains

ester functional group,
always break ester
linkage first !!

CH3

C O CH2CH3

CH3

OH

C COOH

HO CH2CH3

OH
=

Acid
can be formed from a cyanohydrin

Alcohol

C CN
OH

CH3
CH3

C COOH
OH

9647 H2 Chemistry

CH3

Dilute HCl

CH3
heat

HCN in aqNaOH

CH3

C CN
OH

C CH3
O

10-20C

Page 5 of 25

N10/II/4
4
Most of the chemistry of magnesium relates to its ionic compounds. However,
magnesium does form an important group of covalent compounds which are known as
Grignard reagents.
In 1911, the French chemist F.A.V. Grignard reacted small pieces of magnesium with a
warm solution of bromoethane in a dry, non-polar solvent and obtained a solution
containing ethylmagnesium bromide, C2H5MgBr. Many Grignard reagents, with
different alkly and aryl groups, have now been prepared and are widely used in organic
syntheses.
A typical example of the use of a Grignard reagent is the two-step reaction of
C2H5MgBr with propanone as shown below.

OMgBr
C2H5MgBr + CH3COCH3

(a)

CH3

C CH3

OH
CH3

C 2H 5

C CH3

+ MgBrOH

C 2H 5

State the type of reaction taking place in step I and II.

Step I: nucleophilic addition
Step II: hydrolysis

MgBr

(b)

Suggest the structural formula of the final organic product when

reacted with ethanal in a similar two-step process.

is

OH
CH3

(c)

C H

The Grignard reagent CH3CH2CH2MgBr can be readily converted into a

carboxylic acid by using carbon dioxide.
Suggest a two-step reaction sequence for this conversion, giving structural
formulae for the compounds involved.

CH3CH2CH2MgBr + CO2

9647 H2 Chemistry

Page 6 of 25

Product from Step I:

Product from Step II:

OMgBr

OH

C O

C O

CH3CH2CH2

CH3CH2CH2

J97/I/17 (modified)
5
Three compounds E, F and G all have the molecular formula C3H6O. E is an alcohol, F
is a ketone, and G is an aldehyde.
(i) Draw possible structural formulae for E, F, and G.

CH2=CHCH2OH or CH3CH=CHOH

CH3

CH3

G
(ii)

C CH3

CH2

C H
O

Describe tests (reagents, conditions and observations with each compound) that
would allow you to show that:
1. E is an alcohol, whereas F and G are not.
2. F and G are carbonyl compounds, whereas E is not.
3. G is an aldehyde, whereas E and F are not.
Write balanced equations for all reactions that occur.

1. E is an alcohol, whereas F and G are not.

Test: Add PCl5 to three test tubes containing compound E, F and G at room temperature
and pressure. Test gas evolved with moist blue litmus paper.
Observation:
No steamy white fumes of hydrogen chloride will be observed and moist blue litmus
paper remained blue for compounds F and G.
Steamy white fumes of hydrogen chloride will be observed moist blue litmus paper
turned red for compound E.
Equation:

H2C CHCH2OH +

9647 H2 Chemistry

PCl5

H2C CHCH2Cl + POCl3 + HCl

Page 7 of 25

2. F and G are carbonyl compounds, whereas E is not.

Test: Add 2,4-dinitrophenylhydrazine to three test tubes containing compound E, F and G
and warm.
Observation:
No orange precipitate will be formed for compound E.
Orange precipitate will be formed for compound F and G.
Equation:
CH3
H3C C CH3
O

CH3

CH2

NO2

+ H2N NH

H3C C N NH

O2N

C H + H2N NH
O

NO2 + H2O

O2N

NO2

CH3

CH 2

NO2 + H 2O

C N NH
H

O2N

O2N

3. G is an aldehyde, whereas E and F are not.

Test: Add Tollens reagent to three test tubes containing compound E, F and G separately
and warm.
Observation:
No silver mirror will be formed for compound E and F.
Silver mirror will be formed for compound G.
Equation:

CH3

CH2

C H
O

2[Ag(NH3)2]+ + 2OH-

CH3

CH2

C O-NH4+ + 2Ag
O

+ H2O +

9647 H2 Chemistry

3NH3

Page 8 of 25

An alcohol J, C8H10O, burns in air with a smoky flame.

It can undergo a series of reactions with reagents giving organic products K to O as
shown below:

I2, NaOH (aq)

oxidation
PCl5
J

N
dehydration
HCl

O
(a)

What structural feature must be present in K for it to give a positive test with alkaline
aqueous iodine in forming L and M? Hence, state the class of compound K belongs
to.
J undergoes oxidation to give K

K could be a ketone

[1]

(b)

C CH3

K must contain

structure. [1]

Deduce the identity and structural formula for each of the compounds J to O.

J burns with a smoky flame and has comparable C and H atoms with no of C
atoms 6.

J contains benzene ring.

If J can be oxidised to K, a ketone.
CH3 CH
J must be a 2 alcohol containing this structure

OH
H
J is

K is

C CH3

OH
[1]

9647 H2 Chemistry

C CH3

[1]

Page 9 of 25

C OL is

and M is

O
[1]

CHI3
[1]

J undergoes nucleophilic substitution with PCl5 to form N.

N must be a halogenoalkane

N is

C CH3
Cl

[1]

J undergoes elimination to form O.

O is an alkene

H H

O is

C C H
[1]

O undergoes electrophilic addition to form N.

N is confirmed to be a halogenoalkane

(c)

State the reagents and conditions necessary to make the following conversions:
(i)
J to K
(ii)
J to O
(i)

J to K
Reagents : K2Cr2O7 in dilute H2SO4 [1]
Conditions : reflux

(ii) J to O
Reagents : concentrated H2SO4
Conditions : heat at 170C

9647 H2 Chemistry

[1]

Page 10 of 25

[Deductive Question]
A certain industrial cleaner and paint solvent was distilled to produce a single
compound D. When D reacted with 2,4-dinitrophenylhydrazine, an orange precipitate
was produced. With alkaline aqueous iodine, D gave a pale yellow precipitate. D did
not react either with warm acidified potassium dichromate (VI) or with aqueous
bromine. Reduction of D with hydrogen over a catalyst produced equimolar mixture of
two isomers, E and F, with the molecular formula C4H10O.
Suggest structural formula for D, E and F and explain the reactions involved.

D undergoes condensation with 2,4-DNPH.

D is a carbonyl compound.
Orange ppt is a hydrazone.

D undergoes oxidation with warm alkaline aqueous I2.

D contains

O
CH3

structure

OH
CH3

pale yellow ppt is CHI3

D cannot have

D has a carbonyl group and the reduction of D

gives products with only one O atom.
Therefore, D cannot have both a carbonyl and a
hydroxyl group

9647 H2 Chemistry

Page 11 of 25

D does not undergo oxidation with K2Cr2O7.

D is a ketone (not an aldehyde)
(Ketones are resistant to oxidation)

D does not undergo electrophilic addition with Br2 (aq).

D does not have

C structure.

D (ketone) undergoes reduction to give E and F. (C4H10O)

E and F has no of C atom 6, they must be 2 aliphatic
alcohols.
D must be an aliphatic ketone.

OH
E and F

CH3 C* CH2 CH3

H

Both E and F contain a chiral carbon hence they are optical isomers. A

racemic mixture is formed

OH
CH3

OH

C
H

D is

CH2CH3

CH3CH2
H

CH3

O
CH3

9647 H2 Chemistry

CH2 CH3

Page 12 of 25

[Chemical Tests]
Three different compounds of molecular formula C8H8O give precipitates with
2,4-dinitrophenylhydrazine and can be reduced by lithium aluminium hydride in dry
ether to compounds of molecular formula C8H10O.
Suggest structures for these three compounds and explain how they could be
distinguished from one another by means of chemical tests.

[The isomerism does not arise from a difference in the orientation of substituents in
the benzene ring.]
All three compounds contain comparable no of C and H atoms with no of C atom 6.
All contain benzene ring.
All three compounds undergo condensation with 2,4-DNPH to form orange ppt.
All three are carbonyl compounds
All three compounds undergo reduction with LiAlH4 to form alcohols.
3 possible structures (C8H8O) :

H O

C CH3

C C H

O
CH3

C H

H
A (aromatic ketone)

B (aliphatic aldehyde)
NOT AROMATIC!!

C (aromatic aldehyde)

Step 1: To distinguish A from B and C

Test : Add aqueous iodine and aqueous NaOH to compound A, B and C separately and
warm.
Observations: pale yellow ppt obtained Compound A
No pale yellow ppt Compound B and C

Step 2: To distinguish B and C,

Test : Add Fehlings solution to compound B and C separately and warm.
Observations: Reddish brown ppt obtained Compound B
No reddish brown ppt Compound C

9647 H2 Chemistry

Page 13 of 25

N07/P3/Q3(d)
9
In 1834 the French chemist Eugene Peligot published his investigations into the action
of heat on the Group II salts of carboxylic acids. He discovered that the salts
decomposed to give the metal carbonate and a carbonyl compound. This calcium
ethanoate produces propanone.
(CH3CO2)2Ca
CaCO3 + (CH3)2CO
When this reaction is carried out by heating a 1:1 molar mixture of calcium ethanoate
and calcium methanoate, (HCO2)2Ca, a mixture of three carbonyl compounds is
formed, all having Mr < 60.
(a)

Suggest the structures of the three carbonyl compounds, and the ratio in which they
might be produced.

O
CH3

C CH3

O
H C CH3

O
H C

Ratio is propanone : ethanal : methanal = 1:2:1

(b)

Suggest two chemical tests that could be used to distinguish the three carbonyl
compounds from each other. You should state what you would observe for each
compound in each test.

(i)

Add Tollens / Fehlings Reagent to the 3 compound in separate test tubes and
warm. A silver mirror is formed in the test tubes of methanal and ethanal, while no
silver mirror seen in the test tube containing propanone.

(ii)

Add aqueous iodine with sodium hydroxide to the 2 compounds in separate test
tubes and warm. The brown iodine decolourised and a pale yellow precipitate
appears in the test tubes containing ethanal while the test tube containing methanal
remains brown with no yellow precipitate being formed.

Alternative answer:
(i) Aq. Iodine with sodium hydroxide, warm
(ii) Tollens / Fehlings Reagent

9647 H2 Chemistry

Page 14 of 25

10

[Planning]
A student was given 4 unlabelled bottles and each bottle contains one of the
following organic compounds: cyclohexene, butan-1-ol, benzaldehyde, propanone.
Outline a sequence of simple chemical tests by which the studen could identify each
of the above organic substances. The student is not allowed to identify the
substances by elimination.

Test

Procedure

Observation

Place 1 cm3 of each of the

organic compounds to 4
separate test tubes.

Decolourisation of
reddish-brown
solution is seen
for the test tube
containing
cyclohexene.

Add 2-3 drops of Br2 in CCl4,

rtp

Chemistry Involved

No
decolourisation
of reddish-brown
solution is seen
in the other test
tubes.
2

Place 1 cm3 of each of the

other organic compounds to 3
separate test tubes.
Add 1g of PCl5(s), r.t.p

White fumes of
HCl produced,
which turn damp
blue litmus paper
red is seen for the
test tube containing
butanol
No white fumes
are seen in the
other test tubes.

Place 1 cm3 of each of the

other organic compounds in 2
separate test tubes.
Add 2 cm3 of Tollens
reagent.
Warm the mixtures in a water

9647 H2 Chemistry

Silver mirror is
observed in the
test
tube
that
contains
benzaldehyde.

Benzaldehyde
undergoes oxidation
reaction Tollens
reagent to give a silver
mirror.

No silver mirror
is observed in the

Page 15 of 25

bath for 2-3 minutes

other test tubes.

Place 1 cm3 of the remaining

organic compound in a test
tube.

Orange ppt of
hydrazone is
formed for the test
tube containing
propanone.

Add 3 cm3 of 2,4dinitrophenylhydrazine

dropwise.

Propanone undergoes
condensation with 2,4dinitrophenylhydrazine

Heat the mixtures in a water

bath for 5-10 minutes

Alternative test:
Place 1 cm3 of each of the
other organic compounds in a
test tube.
Add 1 cm3 of I2 (aq) and 1 cm3
of NaOH aqueous. Warm the
mixture

Decolourisation
of brown iodine
solution.
Pale
yellow ppt of CHI3
is formed for the
test tube containing
propanone.

THE END

9647 H2 Chemistry

Page 16 of 25

Name:

Date:

Class:

Score:

/20

Assignment Carbonyl Compounds

N07/III/4
(a)
(i)

Write an expression for the acid dissociation constant, Ka, for the weak acid
hydrocyanic acid, HCN.

H+(aq) + CN-(aq)

HCN(aq)

Ka
(ii)

H CN

HCN

[1]

For HCN, Ka = 4.9 x 10-10 mol dm-3. Use this value to calculate [H+] in a
0.100 mol dm-3 solution of HCN, and hence calculate the percentage of HCN
molecules that are ionised.

HCN(aq)

H+(aq) + CN-(aq)

4.9 1010 0.100 7.00 106 moldm3 [1]

% of HCN molecules ionized =

7 106
100% = 0.00700% [1]
0.100

(i) Explain how the addition of solid sodium cyanide, NaCN, will alter the
percentage of HCN molecules ionised.

HCN(aq)

H+(aq) + CN-(aq)

Adding NaCN will increase the concentration of CN- ions in the solution. By Le
Chateliers Principle, the equilibrium position will shift to the left [1] to reduce the
concentration of CN- ions, thus lowering the % ionisation of HCN [1].
(b)

(i) What is understood by the term order of reaction?

Order of reaction is the power to which a concentration of reactant is raised to in
the rate equation. [1]

9647 H2 Chemistry

Page 17 of 25

Cyanohydrins are useful intermediates in organic syntheses. They can be made by reacting
ketones with a solution of HCN to which a small amount of NaCN has been added.

(CH3)2CO + HCN

(CH3)2C(OH)CN

In a series of experiments, the reaction was carried out with different concentrations of the
three reagents, and the following relative initial rates were obtained.
Experiment
number
1
2
3
4

[(CH3)2CO] /
mol dm-3
0.040
0.050
0.040
0.050

[HCN] /
mol dm-3
0.040
0.040
0.040
0.050

[NaCN] /
mol dm-3
0.008
0.008
0.006
0.006

Relative initial rate /

mol dm-3 s-1
1.00
1.25
0.75
0.94

(ii) Use these data to deduce the order of reaction with respect to each of the three
reagents showing how you arrive at your answers. Hence write a rate equation
for the reaction.
Let Rate = k[propanone]a[HCN]b[NaCN]c
From Experiment 1 & 2

Rate1 k 0.040 0.040 0.008

1.00

a
b
c
Rate2 k 0.050 0.040 0.008
1.25
a

Solving, a = 1.
Order of reaction is 1 wrt propanone. [1]
From Experiment 1 & 3

Rate1 k 0.040 0.040 0.008

1.00

a
b
c
Rate3 k 0.040 0.040 0.006
0.75
a

Solving, c = 1.
Order of reaction is 1 wrt NaCN. [1]
From Experiment 1 & 4

Rate1 k 0.040 0.040 0.008 1.00

Rate 4 k 0.05010.050b 0.0061 0.94

1

Solving, b = 0.
Order of reaction is 0 wrt HCN. [1]
Rate = k[propanone][NaCN] [1]

9647 H2 Chemistry

Page 18 of 25

(iii) Describe a mechanism that is consistent with your rate equation, and indicate
which step in the mechanism is the rate determining step. Explain your reasoning.
(CH3)2CO + HCN

(CH3)2C(OH)CN (Overall eqn)

Rate = k[propanone][NaCN]

(rate eqn)

Rate equation is not based on the overall stoichiometric chemical equation but on the R.D.S.
of a multiple-step mechanism. [1] Since order of reaction wrt HCN is 0, HCN is not
involved in the slow step. Reaction is non-elementary with the rds involving 1 propanone
molecule and 1 NaCN molecule.

HCN(aq)

Step1:

H+(aq) + CN-(aq)

NaCN Na+ + CN

O-

C CH3 + CN-

CH3

CH3

C CH3
CN

Step2:

OCH3

C CH3 + HCN

OH
CH3

CN

Step3:
[3]

C CH3 + CNCN

for mechanism ( -1 for any mistake)

(iv) Hence suggest why propanal, CH3CH2CHO, reacts with HCN at a faster rate than
does propanone.
Propanone consists of 2 bulky methyl groups around the carbonyl carbon, creating more
steric hindrance for the attack of the nucleophile.
OR
The 2 electron donating methyl groups dispersed the positive charge on the carbonyl
carbon to a larger extent on propanone than pronanal, making it less susceptible to
nucleophilic attack. [1]

9647 H2 Chemistry

Page 19 of 25

(v) State the roles of HCN and NaCN in the mechanism of this reaction.
HCN is the reactant and NaCN is the catalyst. [1]
(c)

The reaction between propanal and HCN produces an equimolar mixture of two
isomers D and E. When the vapour of either isomer is passed over hot aluminium
oxide, the same mixture of two cyanoalkene isomers F and G is produced.
Describe the types of isomerism shown here.
Explain why each of the two isomers D and E produce that same mixture of
cyanoalkenes.
You should include the displayed formulae of all the compounds D - G in your answer.
Type of isomerism shown in D and E: optical isomerism [1]

H
O

O
C
N C
H
H C H

C N
H C H

H C H

H C H

[1] for both

Type of isomerism shown in F and G: geometrical isomerism [1]

H
C C
N

C
C C

H
H

H C C H
H H

H C C H
H H

F(cis-isomer)

G(trans-isomer) [1] for both

Both D and E undergoes elimination of H2O from the same adjacent carbon atoms
to give the same product which could exist in two different ways, due to restricted
rotation about the C=C double bond. [1]

END

9647 H2 Chemistry

Page 20 of 25

Additional Challenging/ Practice Questions

(Tutors may use these as extra practice for advanced classes)
1.

Carvone, C10H14O, is the main flavoring material in spearmint oil. It reacts with
2,4-dinitrophenylhydrazine to yield an orange precipitate but does not react with
Tollens reagent. When carvone is treated with hydrogen gas in the presence of a
nickel catalyst, it reacts to yield a compound A (see below). Carvone can also
undergo oxidation with acidified KMnO4 under several hours of reflux to form
compound B (see below), carbon dioxide and water.

OH
CH
CH3

CH2

CH

CH

CH2

CH3
CH

CH2

CH3

HO

C
O

CH2

CH

CH2

C O

CH3

CH3

Deduce the structural formula of carvone, showing your reasoning.

Carvone undergoes condensation with 2,4-DNPH.

Carvone is a carbonyl compound.
Carvone does not undergo oxidation with Tollens.
Carvone could be a ketone.
Carvone undergoes reduction to produce A, which consist of a 2o alcohol it
contains a ketone
From the structure of A, carvone is a cyclic compound. When it undergoes strong
oxidation with acidified KMnO4, a straight chain molecule is formed (compound B).
C=C bond present within the 6-C ring.
Strong oxidation of carvone also produces CO2 and compound B has 9 carbon,
instead of 10 carbon in A, this suggest C=CH2 / terminal double bond is present in
carvone.
C=C double bonds in carvone are reduced to saturated compound A with H2.

Structural formula of Carvone:

O
CH
CH3

CH2

CH2

CH C
CH

CH2

9647 H2 Chemistry

CH3

Page 21 of 25

08/NJC/III/1(c)
2

Grignard reagent, RMgCl, is useful in organic synthesis as it enables the combination

of two organic molecules into a bigger one by forming a carbon-carbon bond. It is
prepared by the reaction of magnesium with a halogenoalkane. One of the most
important uses bond
of the
Grignard
The carbon-magnesium
is highly
polar,reagent is its reaction with carbonyl compounds to
form alcohols as shown below.
R'

R'
R

MgCl +

H2O

OH

Mg(OH)Cl

H
Given the carbon-magnesium bond in Grignard reagent is highly polar,
state the type of reaction between R MgCl and the aldehyde.

(i)

nucleophilic addition
(ii) R-MgCl reacts with propanal to give compound A. Compound A gives a yellow
precipitate with I2 in aqueous NaOH. When compound A reacts with excess
concentrated H2SO4 at 170oC, compounds B and C are formed. Compound B
upon reaction with hot acidified potassium manganate(VII), produces compound
D and effervescence is observed. Compound C exists as a pair of geometric
isomers. Deduce the structure of compounds A - D.
By observing pattern in general eqn given above,
R-MgCl + CH3CH2CHO CH3CH2CH(OH)(R) +Mg(OH)Cl
Compound A

A undergoes oxidation with alkaline aqueous iodine.

A contains -CH(OH)CH3 structure

Compound A
H

H3C

CH2CH3

OH

A undergoes elimination to form B and C.

B and C are alkenes.

B and C could be:

H

C
CH2CH3

H3C

CH3

C
H

9647 H2 Chemistry

H3C

C
H

C
CH3

Page 22 of 25

 B undergoes oxidation to give D with CO2 produced.

B must contain terminal C=C double bonds.
H

C
Compound B is

CH2CH3

HO
O

Compound D is

CH2CH3

C exists as cis-trans isomers hence there must be 2 different groups attached to

same C of each double bond.

Compound C
H3C

CH3

C
H

9647 H2 Chemistry

H3C

C
H

C
CH3

Page 23 of 25

Multiple-Choice Questions
1.
For which one of the following can a solution of iodine in aqueous sodium hydroxide
be used to distinguish between members of the pair?
A. CH3CHO and CH3COCH3
B. CH3CH2CHO and CH3COCH3
C. CH3CH2OH and CH3CH2CH(OH)CH3
D. CH3OH and CH3CH2CHO
2.

Which reagent gives the same visible result with propanal and with propan-2-ol?
A. 2,4-DNPH
B. acidified potassium dichromate (VI)
C. concentrated sulphuric acid
D. Tollens reagent

3.

Why does hydrogen cyanide add to propanone but not to propene?

A. The addition product formed with propene would not be stable.
B. Propanone is more susceptible to nucleophilic attack than propene.
C. Propanone is more susceptible to electrophilic attack than propene.
D. The two methyl groups in propanone donate electrons more
effectively than the single methyl group in propene.

4.

The product of the reaction between propanone and hydrogen cyanide is hydrolysed
under acidic conditions.
What is the formula of the final product?
A. CH3CH2CH(OH)CO2H
B. CH3CH2CH2CO2H
C. (CH3)2CHCONH2
D. (CH3)2C(OH)CO2H

5.

Which statement about phenylethanone and ethanal is incorrect?

A. Both may be prepared by the oxidation of an alcohol.
B. Ethanal changes the colour of warm acidified potassium dichromate (VI) from
orange to green, but not phenylethanone.
C. Both react with 2,4-dinitrophenylhydrazine reagent.
D. Phenylethanone gives a negative while ethanal gives a positive
tri-iodomethane test.

6.

A compound R has the following properties :

it is neutral
it gives an orange precipitate with 2,4-dinitrophenylhydrazine
it evolves hydrogen chloride when treated with PCl5 at room temperature
it gives a negative test with Tollens reagent
What could R be?
A.
CHOCH2CH2OH
B.
(C6H5)COOCH3
C.
(C6H5)COCH2OH
D.
CH3(C6H5)COOH

9647 H2 Chemistry

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7.

The reaction in which two ethanal molecules combine to form a compound is

commonly known as an aldol reaction (Reaction I). Aldol forms another compound on
heating as illustrated in Reaction II.
I
2 CH3CHO CH3CH(OH)CH2CHO
II
CH3CH(OH)CH2CHO CH3CH=CHCHO + H2O
Which of the following best describes reactions I and II?
I
addition
addition
elimination
substitution

A
B
C
D
8.

II
elimination
reduction
reduction
elimination

All of the following reagents react with ethanal, CH3CHO.

Which reagent will give a product that retains the C-C=O structure?
A. 2,4-dinitrophenylhydrazine
B. ethanolic hydrogen cyanide
C. lithium aluminium hydride
D. potassium manganate (VII)

N07/P1/Q23(H1)
9
A compound, X, of molecular formula C5H10O showed the following behavior.
It gave an orange precipitate with 2,4-dinitrophenylhydrazine reagent.
It gave a yellow precipitate when warmed with alkaline aqueous iodine.
It showed no reaction with Fehlings reagent.
Which is the correct formula of X?

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

A.

H H

H H H H

H C C C C C
H

H H H H

B.

H H H

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

C.

H H
H C C
D.

9647 H2 Chemistry

H CH3

H
C C
H

O
H

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