CHM412 CHAPTER 5

EXERCISE 1& 2 ALCOHOLS & PHENOL

1. Give the IUPAC name for each compound.

a) b)

c) d)

e) f)

2. Draw the structure corresponding to each IUPAC name.

b)
a)

d)
c)

e) f)
 CHM412 CHAPTER 5
EXERCISE 1& 2 ALCOHOLS & PHENOL

3. Fill in the blanks in the table below with a suitable answer.

Reactant/structure Reagent(s)/reagent name Observation

a) I2/NaOH Yellow precipitate with

antiseptic smell

b) CH3CH2CH2CH2OH Na (sodium metal)

c) CH3CH2CH2CH2OH + CH2COOH acidic condition

d) Lucas test immediate cloudiness

(concentrated HCl + ZnCl2)

e) C6H5OH (phenol) Bromine water

4. Explain a chemical test to differentiate 1-propanol and 2-propanol.

5. Outline the following synthesis. Give reagents and reaction conditions.

6. Predict which member of each pair has the higher boiling point, and explain the reasons for your prediction.
(a) 2-hexanone or 2-hexanol (b) 2-hexanol or 1,5-hexanediol
 CHM412 CHAPTER 5
EXERCISE 1& 2 ALCOHOLS & PHENOL

7. Give the main product of each of the following reaction.

Reactant Reagents Products

1

Na2Cr2O7, H+,

+ H2O
, H+,
3

KMnO4, H+ + MnO2

SOCl2

HBr
 CHM412 CHAPTER 5
EXERCISE 1& 2 ALCOHOLS & PHENOL

PAST YEAR QUESTIONS

QUESTION 1

(a) Write the proper IUPAC names for the following compounds.

(i) (ii) (iii)

(b) Draw the structure formula for each of the following compounds.
(i) trans-2-aminocyclohexanol (ii) 3-hydroxy-2,4,6-trinitrophenol (iii) 2-ethyl-1-methylcyclopentanol

QUESTION 2

Indicate the major and minor structure of the products for the following reaction. Give reason for your decision.

QUESTION 3

(a) Explain a chemical test to differentiate between the following pair of alcohols.
(i) 1-butanol and 2-methyl-2-propanol (ii) 1-propanol and 2-propanol

(b) Consider the following reaction scheme. Draw the structure of A and B.
 CHM412 CHAPTER 5
EXERCISE 1& 2 ALCOHOLS & PHENOL

QUESTION 4

Consider the following scheme.

(a) Suggest chemical structures of C, D, E, F and G

(b) Draw one structure isomer of E which cannot undergo oxidation

QUESTION 5

(a) Suggest the structure of H, I, J, K, L, M,

N and O

(b) State reagent X

(c) Name the mechanism for the reactions

(i) I J
(ii) M N

(d) Does I exhibit geometrical isomerism?

Explain your answer.

QUESTION 5
 CHM412 CHAPTER 5
EXERCISE 1& 2 ALCOHOLS & PHENOL

Give the main product of each of the following reaction.

QUESTION 6

Which is the stronger acid in the following pair? Explain your answer

QUESTION 7

Explain whether the following compounds able to react with acidified solution of potassium permanganate under
heating condition. Draw the structure(s) of the organic product formed.
(a) (CH3)3CCH2OH
(b) CH3CH2C(CH3)2OH
(c) CH3CH2CH(CH3)OH