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Chem 332: Organic Chemistry Iii Question Paper

Chem 332: Organic Chemistry Iii

Course:Bachelor Of Education Science

Institution: Chuka University question papers

Exam Year:2013

CHUKA

UNIVERSITY

UNIVERSITY EXAMINATIONS

THIRD YEAR EXAMINATION FOR THE AWARD OF DEGREE OF
BACHELOR OF EDUCATION (SCIENCE)

CHEM 332: ORGANIC CHEMISTRY III

STREAMS: B.ED (SCIENCE) Y3S2 TIME: 2 HOURS

DAY/DATE: TUESDAY 13/8/2013 8.30 A.M. – 10.30 A.M.
INSTRUCTIONS:

ANSWER QUESTION ONE AND ANY OTHER TWO QUESTIONS.

1. (a) Write the structural formula for each of the following compounds. [5 marks]

(i) Triisopropyl amine
(ii) 4-Methylhexanoic acid
(iii) Methyl propanoate
(iv) Pentanenitrile
(v) Acetophenone

(b) Give the IUPAC systematic names of each of the following compounds.

[5 marks]

(c) Arrange the following carboxylic acids in order of increasing acidity. Explain the rationale for your answers. [4 marks]

(d) Predict the major organic product(s) of each of the following reactions.
[6 marks]

(e) Explain the following observations:

(i) Amines have lower boiling points than alcohols of comparable molecular weights. [2 marks]

(ii) Primary alkylamines are more basic than ammonia. [2 marks]

(iii) Low molecular weight amines are highly soluble in water. [2 marks]

(iv) Amides are far less basic than amines. [2 marks]

(v) Amines that are not soluble in water dissolve in dilute inorganic acids.
[2 marks]

QUESTION 2 (20 MARKS)

2. (a) (i) Show how you might use a cyclic acetal to carry out the following
transformation. [8 marks]

(ii) Why would a direct addition of lithium aluminum hydride to A fail to
give B? [2 marks]

(b) (i) Suggest a plausible mechanism for the following reaction. [8 marks]

(ii) Arrange the following groups on their tendency to migrate in the Baeyer-Villiger oxidation reaction. [2 marks]

Methyl, Phenyl, 2o Alkyl, H

QUESTION 3 (20 MARKS)

3. (a) (i) Show all steps in the aldoladdition that occurs when propanal is treated
with base. [6 marks]

(ii) How would you account for the fact that the product of the aldol addition is 3-hydroxy-2-methyl? [2 marks]

(iii) What products would be formed if the reaction mixture were heated?
[2 marks]

(b) Outline the mechanism of the following reaction. [10 marks]

QUESTION 4 (20 MARKS)

4. (a) Predict the products of each of the following reactions. [10 marks]

(b) (i) Outline the synthesis of p - (Phenylazo) phenol from benzene and phenyl.
[8 marks]

(ii) Why are azo compounds extensively used as dyes? [2 marks]

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Chem 332: Organic Chemistry Iii Question Paper

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