Raffles Junior College

H2 Chemistry 2010/11
Lecture Notes 10 Introduction to Organic
Chemistry
Lecturer: Mrs Kwie Shiao Yin

1. Draw the condensed structural formulae of the following compounds:

(a) 4-bromo-1,2-dichlorobenzene
(c) 3-methylpentanoic acid

(b) 2-methyl-1,3-butadiene
(d) 1,4-dimethylcyclohexene

2. Give the displayed formulae of the following compounds:

(a) 3-phenylbutan-2-ol

(b) 2-aminopentanedial

(c) 2-oxopropanoic acid

3. Give the IUPAC names of the following compounds:

(a)

(b)

OH OH

CH3CHCHCH2CCH2CH
3

(c)

(d)

4. For each of the following compounds

(i) predict the hybridisation and the geometry for each carbon atom
(ii) mark any chiral carbons present with an asterisk.
CH 3

(a)

(b)

Nootkatone
(Grapefruit oil)

CH3

O
Androstene-one

5. Give the structural formulae for all the compounds having the formula C5H10. State
which types of isomerism are involved. Which of these isomers exist as a pair of
stereoisomers?
6. State clearly which types of stereoisomerism are involved and mark any chiral carbons
present with an asterisk. If they do display stereoisomerism, draw the corresponding
stereoisomers.
(a) hex-3-ene

(b) 2-bromobutane

(c) cyclobutane-1,2-dicarboxylic acid

(d) cyclohexene

(e) C6H5CH(OH)CH=CH2

(f) CH3CH=CHCH2CH(OH)CH3

7. Classify each of the following reactions as belonging to a particular category.

(i.e. addition, substitution, elimination, rearrangement, hydrolysis, reduction, oxidation)
(a)

CH3Br

(b) CH2=CH2

H2

(c)

HCN

AlBr3

Pt catalyst

HBr

CH3CH3

alc. KOH
(d) CH3CH2CH2Cl

(e) CH3CH3

Cl2

(h) CH=CH2
HBr(g)

uv light

conc. H2SO4

(f) CH3CH2OH
(g)

CH2=CHCH3 + HCl

heat

H2 O

CH3CH2Cl

+ HCl

CH2=CH2

+ H2 O

CHBrCH3

+ NH4+

CH(OH)CH3
KOH(aq)
warm

Answers to Tutorial: 10
Chemistry

An Introduction to Organic

1. (a)

(c)

(b) CH2=C(CH3)CH=CH2

CH3CH2CH(CH3)CH2COOH

2. (a)

(d)

(b)

3. (a) 3-chloropent-1-ene
(c) 4-ethyl-3,6-dimethyloctane
4. (a)

(c)

(b) 5,6-dihydroxyheptan-3-one
(d) 2-ethyl-1,1-dimethylcyclobutane
(b)

CH 3

*
*

CH3

*
O

Nootkatone
(Grapefruit oil)

All carbons are sp3 hybridised except

the 5 which are double-bonded.
They are sp2 hybridised.
sp3 hybridised tetrahedral around C atom
sp2 hybridised - trigonal planar around C atom

*
*

Androstene-one

All carbons are sp3 hybridised except

the 3 which are double-bonded.
They are sp2 hybridised.

5. C5H10 10 structural isomers

CH3CH2CH2CH=CH2

CH3CH2CH=CHCH3

geometric
isomerism
CH3CH2C(CH3)=CH2

(CH3)2CHCH=CH2

CH3CH=C(CH3)2

Branched-chain isomerism, positional isomerism, functional group isomerism

optical isomers

geometric isomers

6. (a) hex-3-ene: geometric isomerism

(b) 2-bromobutane: optical isomerism

H

C H3C H2

C
*

CH3

H3C

Br

C
*

C H2C H3
Br

mi rror

(c) cyclobutane-1,2-dicarboxylic acid

geometric isomerism

optical isomerism (for trans-isomer)

COOH

COOH

COOH

COOH
mirror plane

(d) cyclohexene: none

(e) C6H5CH(OH)CH=CH2
optical isomerism

(f) CH3CH=CHCH2CH(OH)CH3
geometric & optical isomerism
*

*
H C* O H
C H 2 = CH

HO

C* H
CH =CH 2

mirror plane

m irr or p la n e

*
mirror plane

8.

a.
b.
c.
d.
e.
f.
g.
i.

electrophilic substitution
addition/reduction/catalytic hydrogenation
nucleophilic addition
elimination
free radical substitution
elimination/dehydration
hydrolysis
1st step: electrophilic addition
2nd step: nucleophilic substitution