Chapter 9: Alcohols and Phenol

Tutorial Answers-Chapter 9
1. Give IUPAC names of the following compounds and identify the alcohols as primary,
secondary or tertiary.

(a) CH3 (b) H3C CH2 CH OH

H3C C OH CH3
CH3
Butan-2-ol
2-methylpropan-2-ol
(c) CH3 (d) CH3
H3C CH2 CH2 C OH
H2C CH2
HO
CH2
CH3 3-methylcylcobutanol

4-methyloctan-4-ol
(e) H3C CH2 CH3 (f) CH3
C CH
HO CH2 HO

2-methylpent-2-en-1-ol p-methylphenol

2. Draw chemical structures corresponding to the following IUPAC names.

a) Hexanol b) 2-methylpropan-2-ol

OH
OH

c) 2-methylheptane-2,5-diol d) p-bromophenol
OH HO

OH Br

e) Cyclopentanol f) Pent-3-en-1-ol

1
 Chapter 9: Alcohols and Phenol

OH

OH

g) 3-methylcyclohexanol h) Prop-2-ene-1-ol

OH OH

H3C

3. Draw and name the structural isomers of alcohol with general formula C 4H9OH. Based
on the structures, state the class of each alcohol.

OH
OH

n-butanol 2-butanol
(primary alcohol) (secondary alcohol)

OH HO

2-methyl-2-propanol 2-methyl-1-propanol
(tertiary alcohol) (primary alcohol)

4. Arrange these compounds in order of increasing solubility in water

H3C CH2 CH2 CH2 CH3 HO CH2 CH2 CH2 CH3

A B

H3C CH2 CH2 OH

C
Answers: pentane (A), a nonpolar hydrocarbon, has the lowest solubility in water. Both
propanol (C) and butanol (B) are polar compounds due to the presence of –OH groups, and
each interacts with water molecules by hydrogen bonding. The water solubility of these
compounds are A<B<C

2
 Chapter 9: Alcohols and Phenol

5. Explain the trends in the acidity of phenol and the monofluoro derivatives of phenol.

OH OH OH OH

F
F
pKa 9.95 pKa 8.81 pKa 9.28 pKa 9.81

Answers: The distance between the fluorine atom and the hydroxyl group of phenol is
comparatively smaller in the ortho derivative than that in the other two derivatives and
phenol itself. So the inductive effect will be stronger in the ortho derivative, which is
higher acidity. The phenol without substitution holds the least acidity due to absence of
inductive effect (pKa decreases, acidity increases).

6. Compound P, C4H9Cl, reacts by heating with reagents KOH in ethanol to form Q (C4H8).
The compound Q then undergoes acid catalysed hydration to form R (C4H10O). R does
not react with acidified warm sodium dichromate.

(a) Determine the structure of P,Q and R

Cl HO

R
Q
P

(b) Give a reason why R does not react with acidified warm sodium dichromate.

Because R is tertiary alcohol

3
 Chapter 9: Alcohols and Phenol

(c) Write chemical equation for the conversion of P to Q.

KOH
Cl
Ethanol

P Q

(d) Draw a structural isomer of P.

or or Cl
Cl
Cl

1-chlorobutane 2-chlorobutane 1-chloro-2-methylpropane

7. Compound X is an alcohol. Upon oxidation by acidify potassium permanganate, a

ketone, Y is formed. X reacts with phosphorous bromide (PBr 3) to give Z which is then
purified and reflux in dry ether along with Mg metal to form a Grignard reagent, S. S is
then treated with Y to yield 3,4-di methyl-3-hexanol after hydrolysis in dilute HCl. Identify
X,Y, Z and S. Write all the chemical equations for the reaction involved.

4
 Chapter 9: Alcohols and Phenol

Hint structure: 3,4-dimethyl-3-hexanol

OH

3,4-dimethyl-3-hexanol

H2O/H+

+
MgBr O

S Y

Mg/ether KMnO4/H+

PBr3

Br OH

Z X (secondary alcohol)

8. Describe concisely a chemical test to distinguish

(a) n-butanol and butan-2-ol

Lucas Test, Reagent: ZnCl2 (s) in conc. HCl.
2-butanol: Secondary alcohol, forming white precipitate after about 3 min at 70 C.
n-butanol: Primary alcohol, does not react.

(b) Methanol and isopropyl alcohol

Iodoform Test, Reagent: iodine & sodium hydroxide solution
(To test the presence of CH3-C-OH)
Isopropyl alcohol (CH3)2CH-OH): the appearance of pale yellow precipitate of
triiodomethane, CHI3.
Methanol: does not react
9. Describe how would you distinguish the following pairs,

5
 Chapter 9: Alcohols and Phenol

(a) Benzene and cyclohexane

Using dilute KMnO4 solution

KM nO ( d il)
OH
4

OH
T h e p u r p le c o lo u r d e c o lo u r is e d .

KM nO 4 ( d i l)
N o r e a c t io n

(b) Phenol and toluene

Using aqueous bromine, white precipitation is observed in phenol.
OH OH
Br Br

+ 3 Br2 + 3HBr

Br
CH3

+ 3 Br2 N o o b s e r v a b le c h a n g e

(c) Phenol and benzoic acid

Using FeCl3 solution, blue-violet colouration is observed in phenol.

OH OH

3
+ FeCl 3 FeCl 3

COOH

+ FeCl 3 N o o b s e r v a b le c h a n g e

6
 Chapter 9: Alcohols and Phenol

10. Compound X (C4H9Br) reacts by heating with NaOH in H 2O to form Y. The compound
Y then undergoes acid catalysed hydration by H 2SO4 in 180C to form 2-methyl prop-
1-ene.

(e) Determine the structure of X and Y.

Br HO

X Y

(f) Predict a MAJOR product when compound Y reacts with H2SO4 in 140C.

(g) Draw a structural isomer of X. Name the isomer using IUPAC nomenclature.

or or Br
Br
Br

1-bromobutane 2-bromobutane 1-bromo-2-methylpropane

(h) Describe a chemical test to distinguish between compound Y and 1-butanol.

Answer: Compound Y -Tertiary alcohol – Immediately forms a cloudy solution
as the alcohol is converted to the water insoluble alkyl chloride by a substitution
reaction.
1-butanol- Primary alcohol - Does not react.