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Chem 231: Organic Chemistry Question Paper

Chem 231: Organic Chemistry

Course:Bachelor Of Science In Community Development

Institution: Chuka University question papers

Exam Year:2013

CHUKA

UNIVERSITY

UNIVERSITY EXAMINATIONS
SECOND YEAR EXAMINATION FOR THE AWARD OF DEGREE OF
BACHELOR OF SCIENCE & BACHELOR OF EDUCATION (SCIENCE)
CHEM 231: ORGANIC CHEMISTRY
STREAMS: B.SC &B.ED (SCIENCE) Y2S2 TIME: 2 HOURS
DAY/DATE: WEDNESDAY 17/4/2013 11.30 AM – 1.30PM
INSTRUCTIONS:

ANSWER QUESTION ONE AND ANY OTHER TWO QUESTIONS

QUESTION I (30 MARKS)

(i) Assign the R or S designation to the following stereocenters. [6 Marks]

(ii) Give the IUPAC names of the following compounds. [10 Marks]
HO
(a)

(b)

(c)

NH2
(d) CH3
CH2CH3

CI
(e)

(iii) Predict the major product of each of the following reactions. [10 Marks]

NaBH4
CH3CH2OH
(a)

(b) Hcl
CH3OH

(c) Br + KOCH2 CH3

(d) || AlCl3 + CH3CCI

OH 1. NaH
(e) 2. CH3I
(iv) Explain why ethers make good solvents for organic synthesis. [4 Marks]

QUESTION TWO
(i) Give the product(s) of each of the following reactions indicate the major and minor
products where necessary. [10 Marks]

NaOCH2CH3
(a) CH3CHCH3
CH3 CH2 OH,
Br
NaOCH2CH3
(b) CH3CH2 CH2 Br
CH3CH2OH

KOC(CH3)3
(c) CH3(CH2)5CH2CH2Br
(CH2)3 COH, 40?

CH3
CH3CH2OH
(d) CH3C CH2CH3
25?
Br

(e) Br Acetone

ONa

(ii) Write a plausible reaction mechanism for the major product of the reaction between
tert-butyl bromide and sodium ethoxide. [10 Marks]

QUESTION THREE

(i) What is the major product(s) of each of the following reactions? [10 Marks]

NO2
(a) HNO3

H2SO4

OCH3

(b) CH3CCI

Alcl3

CH2CH3

(c) SO3

H2SO4

OH
HNO3
(d)
H2SO4

Br

CF3

(e) Cl2

FeCl3

(ii) Write the mechanism of the following reaction. [10 Marks]

Alcl3 c(cH3)3
+ (CH3)2CHCH2cl
0? + Hcl

QUESTION FOUR

(i) Predict the products(s) of each of the following reactions. [10 Marks]

mgBr
(a) 1.

2. H30+

(b) 1. Hg(OAC)2,CH3OH
2. Na BH4

HBR (Excess)
(c) CH3

(d) NaOCH3

CH3OH

(e)
1. LiAlH4
2. H3O+

(ii) Propose the mechanism of the following reaction. Show all resonance forms of the
intermediate carbocation. [10 Marks]

OCH3
OCH3
O O
CH3CCl C

AlCl3 + Ch3

C
O CH3
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Chem 231: Organic Chemistry Question Paper

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