CHEMISTRY OF DEPARTMENT

CHE 232 Organic Chemistry Assignment 1

Thursday, 2nd September 2010

Time: 1900 to 2100 hrs

The first assignment for CHE 232 organic chemistry is scheduled for Thursday, 2nd
September 2010 at 7 to 9 pm. The assignment exercise will take the usual form of an
open-book-test in which students are allowed to bring only textbooks and no other
materials into the test room. The practice questions from which the assignment questions
will be set are as given below. Students are advised to work through all the practice
questions thoroughly and seek help from the CHE 232 lecturers and/or tutors when they
have difficulties. Students are allowed to bring only textbooks into the assignment
rooms. Any student caught with written answers in the body of a textbook will be
disqualified from the assignment exercise.

Q1 In each of the following compounds indicate the hybridisation of each carbon atom
and give approximate values of all the bond angles.

a. CH3C CH b. CH3CH CH2

c. CH3CH2CH3 d. CH2 CH CH CH2

Q2 Arrange the following carboxylic acids in order of decreasing acidity.

O O O O O

H3 C OH ClCH2 OH BrCH2 OH ICH2 OH FCH2 OH

A B C D E

Q3 Write a structure for each of the listed compounds. Explain why the name given here
is incorrect and give a correct name in each case.
a. 1-methylbutane
b. 2-ethylbutane
c. 2,3-dibromopropane
d. 1,3-dimethylcyclopropane
e. 4-chloro-3-methylbuatne
f. 1,1,3-trimethylpenatane
g. 2,2-Dimethyl-6-ethylheptane
 h. 4-Ethyl-5,5-dimethylpentane
i. Cis-1,5-dimethylcyclohexane
j. 2-Isopropyl-4-methylheptane

Q4 Draw structures corresponding to each of the following systematic names.

a. 4,5-Diisopropylnonane
b. Propylcyclopentane
c. 3,4-Dimethyloctane
d. Isoheptyl alcohol
e. (Z)-3-Methyl-2-heptene
f. 3-Isopropyl-2-heptene
g. 6-Bromo-2,3-dimethyl-2-hexene

Q5 Using structural formula, write equations for the following reactions and name each
organic product.
a. the complete combustion of hexane
b. the complete combustion of cyclohexane
c. the monobromination of butane
d. the monochlorination of cyclopentane
e. the complete chlorination of propane

Q6 Write all the steps in the free radical mechanism for the monochlorination of ethane.
What trace products would you expect to be formed as a consequence of the chain
terminating step.

CH 3CH3 + Cl2 light CH3CH2Cl + HCl

Q7 How many monochlorination products can be obtained from the following polycyclic
alkanes?

a. b. c.

Q8 Draw Newman projections for eclipsed and staggered conformations of n-pentane,

viewed along the C2 and C3 bond and draw an energy diagram for the conformations.
Q9 Classify each of the following according to whether they are structural isomers,
geometric isomers or conformational isomers.

CH3 CH3

H3C and CH3

i)
CH3

H3C and Br
ii) Br

Cl
CH3 and
iii) Cl

Br CH3
Br Br and
iv)

Br
Br Br

H H H H
v)
and
H CH3 H H

H CH3

Cl Cl

H CH3 H Cl
vi)
and

H Cl H CH3

H H

vii) CH3CH2CH2CHCH3
CH3CHCH2CH2CH3 and
CH3 CH3
Q10 Which of the following compounds can exist as cis-trans isomers? If such
isomerism is possible, draw the structures in a way that clearly illustrates the geometry.

a. 2-pentene
b. 1-hexene
c. 1-chloropropene
d. 3-brormopropene
e. 1,3,5-hexatriene
f. 1,2-dichlorocyclodecene

Q11 Rank the following sets of substituents in order of Cahn-Ingold-Prelog priorities:

a. CH3 , -OH, -H, -Cl

b. CH3, CH2CH3 , C CH2 , CH2OH

H

c. COOH, CH2OH C N CH2NH2

d CH3 , Br , H , I
O
e CH3, CH2CH3 , CH2CH2OH , C
CH3
f COOH, COOCH3 , CH2OH , CH3

g CH2CH3 , C CH , C N, CH2OCH3

Q12 -Farnesene is a compound found in the waxy coating of apple skins and ocimene is
found in the essential oil of many plants. Assign E or Z stereochemistry for each of the
double bonds in -farnesene and ocimene.

-farnesene

ocimene
Q13 Classify the following compounds as identical, constitutional isomers,
geometrical isomers or none of the above.

a. cyclohexane and 1-hexene

C2H5 C2H5

b. and

H3C H CH3CH2CH2 CH3

c. H CH2CH2CH3 and H H

H3C CH3
d. H2C CHCH2CH3 and
H H

e. cyclopentane and cyclopentene

Q14 Give IUPAC names of the following compounds. Include the E,Z designations
where appropriate.

CH3
a. CH(CH2)3CH b. H2C CHCH2CH2CH3
CH2
CH3

C2H5
c. d.

C2H5

CH3CH2CH2CH2
H CH2
e. f.
H3C H

g. h.

H CH3
H
H
Q15 Give two chemical tests that can be used to distinguish between 1-pentene and n-
pentane.

Q16 Draw curved arrows to show the flow of electrons responsible for the conversion of
reactants into products.

O O

a. CH3 C OCH3 CH3 C CH3 + CH3O

CH3

b. CH3 C C H + NH2 CH3 C C + NH3

c. CH3CH2 Br + CH3O CH3CH2 OCH3 + Br

Q17 Give the organic products expected when 2-methylpropene reacts with each of the
following reagents, where possible indicate the major products.
a. Br2 in CCl4 solvent
b. O3, -78 C then Zn, H3O+
c. O2, flame
d. OsO4, H2O, NaHSO3
e. H2, Pt/C
f. BH3, THF, H2O2, OH-
g. HBr, peroxides
h. CH3OH/H+
i. H2O/H+

Q18 Propose a mechanism for the following reaction and sketch an energy profile
diagram that shows what is happening.

OH

H2O/H+

Q19 How would carry out the following transformations? Indicate the proper reagents.

H OH
OH
?
a. H

H OH

?
b.

?
c. CH3CH CHCH(CH3)2 CH3CHO + (CH3)2CHCHO

?
d. H2C C(CH3)2 (CH3)2CHCH2OH
Q20 Suggest structures of alkenes that give the following reaction products. There may
be more than one answer for some cases.

a. ? H2/Pd/C
2-methylhexane

b. ? H2/Pd/C
1,1-dimethylcyclohexane

c. ? Br2/CCl4 2,2-dibromo-5-methylhexane

d. ? HBr/peroxides 2-bromo-3-methylheptane

e. ? HCl/ether 2-chloro-3-methylheptane

Q21 The acid-catalysed hydration of 1-methylcyclohexene gives 1-methylcyclohexanol.

Write every step in the mechanism of this reaction.
OH
H2 O/H+