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Scheme past year semester 2- 1 Edition

Chapter 16 Hydroxyl Compounds

Question Section Answer

Jan 99 Explain briefly the following observations:


1.
i) Phenol dissolves in aqueous sodium hydroxide but cyclohexane does not.

Phenol dissolve in aqueous NaOH because it is a weak acid. It react with strong
base NaOH to form soluble salt.

OH ONa
NaOH
+ H2O

soluble salt

Cyclohexane is a weak base does not react with NaOH

ii) Ethanol reacts with iodine in aqueous solution of sodium hydroxide forming
yellow precipitate but 1-propanol does not

• Ethanol gives +ve test with Iodoform reagent, because it has methyl alcohol
structure, when it oxidised with Iodoform reagent a methyl carbonyl structure
compound is formed.
• 1-propanol gives –ve test with Iodoform reagent, no methyl alcohol structure.

iii) Write a chemical equation for the reaction between ethanol and iodine in aqueous
solution of sodium hydroxide.

O
I2, NaOH
CH3CH2OH CH3CH

I2, NaOH

O
CHI3 + HCO
yellow ppt

June 99 a) Give suitable chemical tests to distinguish the following pairs of compounds by
2. specifying the necessary reagents, appropriate observations and chemical
equations involved.
i. C6H5CH2OH and C6H5OH
ii. CH3CH(OH)CH2CH2CH3 and (CH3)2C(OH)CH2CH2CH3

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Scheme past year semester 2- 1 Edition

i) Benzyl alcohol react with Lucas’s reagent, solution turns cloudy immediately,
phenol does not react with Lucas’s reagent.

Lucas reagent

ZnCl2, HCl
CH2OH CH2Cl

ii) 2-pentanol reacts with acidified KMnO4, purple colour disappear, brown
precipitate is formed. 2-methyl-2-pentanol does not react, purple colour
remain.
KMnO4,/H+
O
CH3CH(OH)CH2CH2CH3 CH3CCH2CH2CH3 + MnO2
brown precipitate

b) Give chemical equations involved in the following conversions:


i. 1,2-propanediol from 1-propanol
ii. cyclohexylmethanol from chlorocyclohexane
iii. 1-methylcyclohexanol from cyclohexanone

i)
H2SO4(con)
HOCH2CH2CH3 H2C CHCH3
heat
KMnO4,/OH-
cold

H2C CHCH3
OH OH

ii)
Cl MgCl

Mg/ether

i. HCHO
ii. H3O+

CH2OH

iii)
O CH3
i. CH3MgBr OH
ii. H3O+

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Scheme past year semester 2- 1 Edition

June 00 Based on the molecular formula of C6H14O, draw the structural formulae for two
3. tertiary alcohols. Then draw and label the structural formula of an alcohol which
contains primary and secondary carbons atoms. State whether this alcohol is
optically active

CH3 CH3
CH3CCH2CH2CH3 CH3CH2CCH2CH3

OH OH
(I) (II)

C6H14O
CH3
CH3CHCH2CHCH2OH

OH
20 10

CH2OH CH2OH
C C
H H
CH2CH3 H3CH2C
OH OH

Optically active because : 1) molecule contained a chiral center/chiral carbon


2) Molecule not super imposable with its mirror image

The following equation shows the dehydration of an alcohol forming an alkene.


4.
CH3 Conc. CH3
CH3 H2SO4
OH CH3
Major product

Show the mechanism for the formation of the major product. Draw the structure of
another possible product and state the rule applied in determining the major
product.

CH3 CH3
H2SO4(con)
CH3
heat
OH CH3
major product

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Scheme past year semester 2- 1 Edition

Mechanism:

CH3 CH3
CH3 + H+ CH3
OH OH2

CH3 CH3
CH3 CH3
OH2

CH3 1,2 methyl shift CH3


CH3
CH3

CH3 CH3
H+

CH3 CH3

Other product:
CH3 CH3
or
CH3
CH3

Rule applied: Saytzeff’s rule – determines the main product.

2001/02 A compound AA, C3H8O reacts with phosporus pentachloride, PCl5 to form
Session compound BB. Compound AA forms a cloudy solution in 5 minutes after the
5. addition of Lucas reagent. Compound BB reacts with magnesium in ether solvent
to produce CC. The reaction between CC and carbon dioxide, followed by
hydrolysis yields DD. By giving appropriate reasons, draw the structural formulae
of AA to DD and the structural formula for an isomer of AA.
PCl5
C3H8O BB
AA
Lucas's reagent
AA HCl, ZnCl2
cloudy after 5 mins.

BB Mg/ether
CC

i.CO2
ii. H3O+
CC DD
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Scheme past year semester 2- 1 Edition

MgCl
OH
AA: CC: CH3CHCH3
CH3CHCH3

Cl COOH
BB: CH3CHCH3 DD:
CH3CHCH3

Reasons:
* AA is a secondary alcohol as it react with Lucas’s reagent
moderately (cloudy after 5 mins).

* BB is a secondary haloalkane, OH group of alcohol AA is


substitute with Cl when the alcohol react with PCl5.

* CC is a Gridnard reagent as haloalkane reacts with magnesium.

* DD is a carboxylic acid as Gridnard reagent react with CO2


followed by hydrolysis.

Isomer AA is CH3CH2CH2OH

COOH COOCH2CH3
CH3CH2OH/H+
CH3CHCH3 CH3CHCH3 + H2O
heat
ester
DD

COOH NH3, heat CONH2


CH3CHCH3 CH3CHCH3 + H2O
amide
DD

2002/03 The structure of alcohol A is shown as follows:


Session
OH H CH2 CH3
6.
H3C CH2 C C CH2 C CH3

H CH3 H

i) Name compound A according to the IUPAC nomenclature.


ii) Is A optically active? Explain.
iii) Classify alcohol A.
iv) Give the major product of the dehydration of A.

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Scheme past year semester 2- 1 Edition

i) 4,6-dimethyl-2-octanol
ii) Yes, A is optically active because at least there are 3 chiral carbon, at carbon
number 3, 4 and 6.
iii) A is secondary alcohol.
iv) Product of the dehydration of A:

Major product:

7. Given below are the observations from experiments carried out on an alcohol,
C4H10O which has several isomers.

(i) Isomer L does not show any changes upon mixing with Lucas reagent but it
forms butanoic acid upon oxidation with acidified potassium dichromate (IV).
(ii) Isomer M is optically active and gives positive test with I2/NaOH.
(iii)Isomer N reacts instantly with Lucas reagent but it does not change the purple
solution of acidified potassium manganate (VII).

Explain the observations above and deduce the isomers L, M and N.

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Scheme past year semester 2- 1 Edition

HCl, ZnCl2
(i) L no reaction

KMnO4/H+
L CH3CH2CH2COOH

* L is primary alcohol, CH3CH2CH2CH2OH


1-butanol

(ii) M
I2, NaOH
CHI3
yellow precipitate OH

* M has OH group at the second C, C CH3


* M optically active, has chiral C
OH

M is CH3CH2 C CH3

H
2-butanol

(iii) HCl, ZnCl2


N cloudy immediately

KMnO4/H+ no reaction
N

* N is tertiary alcohol, fast reaction with Lucas test & does not oxidised by KM
OH

N is H3C C CH3

CH3
2-methyl-2-propanol

2007/08 The structure of 4-hydroxyazobenzene is as shown


Session
8

Suggest how the above compound can be synthesized using benzene and phenol

con.HNO3 NO2 H2, Pt NH2

con.H2SO4

NH2 N2Cl
NaNO2, HCl
<5oC

N2Cl + OH N N OH