Weekend Assignment 3 Alcohols and Phenols, Carbonyl compounds,

Energetics
1

Lactic acid (2-hydroxypropanoic acid), J, occurs in sour milk. It can be synthesised from
ethanol by the following series of reactions.

I
CH3CH2OH

II
HCN + trace H
NaCN

III
CH3CH(OH)COOH
J

Compounds G and H both react with alkaline aqueous iodine. Compound G reacts with 2,4dinitrophenylhydrazine and also with Fehlings solution. Compound H reacts with sodium
metal.
(a)

(i)

Identify G and H, explain how the identities you suggest fit in with the test reactions
described above.
CH 3
CH 3
C
C
H

H
O

OH
CN

Both compounds G and H undergoes iodoform test with alkaline aqueous

iodine both G and H contains CH(CH3)OH group or -COCH3 group.
G undergoes condensation with 2,4-dinitrophenylhydrazine and oxidation with
Fehlings solution G is an aldehyde
H undergoes acid-metal reaction with sodium metal H is an alcohol

(ii)

Suggest the reagents and conditions for reactions I and III.

Reaction I K2Cr2O7, dilute H2SO4, heat with distillation
Reaction III dilute H2SO4, heat under reflux

(iii)

State the type of reaction in II

[8]
Nucleophilic addition

Weekend Assignment 3 Alcohols and Phenols, Carbonyl compounds,

Energetics

(b)

On heating in the absence of air, lactic acid loses water to give a single compound K,
C6H8O4. K is a neutral compound that does not react with sodium or with 2,4dinitrophenylhydrazine. Suggest the identity of K and explain how it was formed.
O

O
O

esterification occurs between 2 molecules of lactic acid

[2]
2

When under attack, the bombardier beetle uses chemical warfare. It defends itself from
attack by mixing together solutions of hydrogen peroxide and hydroquinone (C6H4(OH)2) in
the presence of enzymes. This reaction releases free oxygen that produce enough energy
to bring the mixture to boiling point. An audible explosion occurs as the beetle to fires a hot
spray at its attacker from its abdomen. Quinone, C6H4O2 is one the products formed.
HO

H2O2(aq)

OH

+ 2H2O (l)

(aq)
(a)

(i)

(aq)

State Hess Law.

The overall enthalpy change for a reaction is equals to the sum of the enthalpy
change of the different individual steps in the reaction, which are measured at the
same temperature and pressure.
[1]

(ii)

Construct an energy cycle and use the following data to calculate the enthalpy
change of reaction inside the beetle
C6H4(OH)2 (aq) C6H4O2 (aq) + H2 (g)
H= +177 kJ mol1
H2O2 (aq) H2O (l) + O2 (g)
H= 95 kJ mol1
H2 (g) + O2 (g) H2O (l)
H= 286 kJ mol1
C6H4(OH)2 (aq) + H2O2(aq)
+177 kJ mol1

95 kJ mol1

C6H4O2 (aq) + 2H2O(l)

286 kJ mol1

[4]

Correct cycle
with correct
species
and state
symbols
Correct
labels/values of
all enthalpies

Weekend Assignment 3 Alcohols and Phenols, Carbonyl compounds,

Energetics
C6H4O2 (aq) + H2 (g) + H2O (l) + O2 (g)

[3]

H = +177-95-286 = -204 kJ mol-1

(b)

When developing exposed film from a camera, aqueous alkaline hydroquinone reacts with
silver ions in a lightactivated reaction in I.

HO

2Ag (aq)

hydroquinone

OH

OH-(aq)
I

quinone

(aq)

NaOH(aq),
followed by CH3 I
II

(i)

Identify X and state the role of hydroquinone in reaction I.

X silver , role of hydroquinone- reducing agent

(ii)

Draw the structural formula of Y and name the type(s) of reaction involved in II.
H 3CO

OCH3

nucleophilic substitution
(iii
)

One student attempts to synthesise hydroquinone from 1,4dichlorobenzene using

hot aqueous sodium hydroxide. State with reasons whether the student would be
successful in his attempt.
No, The C-X bond in 1,4dichlorobenzene is strengthened by overlapping of the
p-orbital of Cl with the orbitals of the benzene ring which results in the
delocalisation of electrons.
or
No, in 1,4dichlorobenzene , overlapping of p orbital of Cl with the
electron cloud of the benzene enables the lone pair of electrons
from Cl to delocalise into the ring. Thus, it reduces the electronwithdrawing effect of Cl. Hence, causes the CCl bond to be less
polar.
or
No, in 1,4dichlorobenzene , the high electron density of the aromatic ring

Weekend Assignment 3 Alcohols and Phenols, Carbonyl compounds,

Energetics
hinders the nucleophilic attack, due to electrostatic repulsion between like
charges. Backside attack of the CCl bond is not favourable.