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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