TUTORIAL 12: INTRODUCTION TO ORGANIC CHEMISTRY

TOPIC 12.1: INTRODUCTION

1. Determine whether the following compounds are saturated or unsaturated:

(a) CH3CH2CH2CH2CH3
(b) CH2=CHCH2CH2CH3
(c)

(d)

(e)

(f)

(g)

(h)
CH(CH 3)2

TOPIC 12.2 : MOLECULAR AND STRUCTURAL FORMULAE

1. (a) Define the term structural formula.

(b) Draw the condensed structure for each of the compounds:
i.

OH

- 29 -
TUTORIAL 12: INTRODUCTION TO ORGANIC CHEMISTRY

ii
O

iii

iv
OH

Cl O

(c) Draw the skeletal structure for each compound given below:
(i) O (ii) CH3 CH3
CH3 CH2 CH2 C CH3 CH3CH CH2CH2CHCH2CH3
(iv) Br
(iii) (CH3)3CCH2CH2CH2OH
CH3CH2CHCH2C OH
O

TOPIC 12.3: FUNCTIONAL GROUPS AND HOMOLOGOUS SERIES

1. (a) Explain the terms functional group and homologous series.

(b) Draw the structural formula for
i. an aldehyde (C5H10O)
ii. a ketone (C4H8O)
iii. a carboxylic acid (C3H6O2)
iv. an amine (C5H13N)
v. an amide (C2H5NO)
vi. an alcohol (C2H6O)
vii. an ester (C3H6O2)
viii. an ether (C2H6O)

- 30 -
TUTORIAL 12: INTRODUCTION TO ORGANIC CHEMISTRY

2. Circle and name the functional groups present in the following molecules:
(a)
CH2OH

NHCH3

(b)
CH2OCH3

NHCOCH 3
(c)
O Cl
COOH
C C H
C
O
C O
O
TOPIC 12.4 : ISOMERISM

1. (a) Define the term isomer.

(b) Draw all posibble isomers of compound with the molecular formula C4H10O and
identify the types of isomerism present.

2. For each of the following compounds, draw its isomeric pair that represents a chain,
positional and functional group isomerism:
(a) CH3CH2CH=CH2
(b) CH3CH(CH3)CH(CH3)CH3
(c) CH3CH2CH2CH2CH2OH

3. (a) What are the essential requirements for a molecule to exhibit cis-trans isomerism?
(b) Which of the following compounds can exist as a pair of cis-trans isomers?
Draw the cis-trans isomers.
i. ClCH=CHCl
ii. BrCH=CHCl
iii. CH3CH=CH2
iv. (CH3)2C=CHCH3

- 31 -
TUTORIAL 12: INTRODUCTION TO ORGANIC CHEMISTRY

v. CH3CH2CH=CHCH3
vi. (CH3)2C=C(CH3)CH2CH3
vii.

Br Br

4. Draw all the structural formulae of alkenes C5H10. Identify the structure that exhibits cis-trans
isomerism.

5. (a) Draw and label the cis-trans isomers of 1,2-dichloroethene.

(b) Suggest which of the isomers has :
i. higher boiling point
ii. higher melting point.
Explain your answers.

6. (a) What is meant by chirality centre?

(b) From the following list, identify the compounds that exhibit optical activity:
i. CH3CH=C(CH3)CH2CH3
ii. CH3CH(OH)CH2CH3
iii. CH3CH2CH(Br)CH2CH3
iv. CH3CH(NH2)COOH

7. (a) State the structural features of a molecule in order to be optically active.

(b) Draw the structural formula of 2-bromobutane and indicate the chiral carbon using an
asterisk (*).
(c) Use a three-dimensional formula to show the structural formulae of enantiomers
in (b).

8. What is a racemic mixture? Why is it optically inactive?

TOPIC 12.5 : REACTIONS IN ORGANIC COMPOUNDS

1. Explain the differences between homolytic cleavage and heterolytic cleavage.

Give one example for each cleavage.

- 32 -
TUTORIAL 12: INTRODUCTION TO ORGANIC CHEMISTRY

2. (a) Define the terms electrophile and nucleophile.

(b) Classify each of the following as electrophile, nucleophile or free radical.
i. NH3
ii. Br
iii. H2O
iv. NO2+
v. NO2
vi. Cl+
vii. BF3
viii. CO2
ix. CH3CH=CH2
x. CH3OH
xi. PCl5

3. Arrange the following carbocations in order of increasing stability.

CH3 CH3 H
+ +
H3C C CH 2 H3C C CH2CH3 CH 3 H3C C CH2CH3
+ +
H

4. Chloromethane reacts with hydroxide ion to form methanol as shown in the equation below.
OH + CH3Cl  CH3OH + Cl
(a) Identify the nucleophile and electrophile.
(b) State the type of reaction.

5. State the type of reactions:

(a)
O O
C OH C Cl
SOCl 2

(b) CH2=CH2 + HCl  CH3CH2Cl

(c) CH2=CH2 + H2O H  CH3CH2OH
2SO 4 ,cataly st

(d) CH3CHBrCH3 KOH

   CH2=CHCH3 + HBr
,alcohol

(e) CH4 + Br2 

uv
CH3Br + HBr

- 33 -
TUTORIAL 12: INTRODUCTION TO ORGANIC CHEMISTRY

(f)
NO2
+ HNO3 H2SO4

(g)
Br H
CH3COOH
CH3CH CH CH3 + Zn CH3C CH CH3

Br

6. Based on the reaction scheme below, state the type of reaction corresponding to steps A, B
and C.

A
CH3 CH3
| Br2 |
CH3CHCH2CH3 uv CH3 CHCH2CH2Br

KOH/ethanol B

CH3 CH3
| HBr |
CH3C(Br)CH2CH3 C CH3C=CH2CH3

Objective Questions

1. The two types of stereoisomers are

A. diastereomers and enantiomers.
B. enantiomers and positional isomers.
C. chain isomers and positional isomers.
D. diastereomers and functional group isomers.

2. Which of the following is a chiral molecule?

A. CH2BrI
B. CH3CBr2Cl
C. (CH3)2CHCl
D. CH3CHBrCH2CH3

- 34 -
TUTORIAL 12: INTRODUCTION TO ORGANIC CHEMISTRY

3. Vinyl acetate is used to make poly(vinyl acetate), PVA, plastic. The structure of vinyl acetate
is shown.
H H O
H C C O C CH3
Based on the given structural formula, vinyl acetate
A. is a cis isomer.
B. is a trans isomer.
C. exhibits structural isomers.
D. contains a chiral carbon atom.

4. The number of possible structural isomers for bromobutane, C4H9Br is

A. 2
B. 3
C. 4
D. 5

5. The functional groups present in the amino acid with the structural formula as shown below
are

HO CH2CHCOOH
NH2

A. alkoxy, carboxy, amide and aromatic ring.

B. alkoxy, carboxyl, amino and aromatic ring.
C. hydroxyl, carboxyl , amino and aromatic ring.
D. hydroxyl, carbonyl, amino and aromatic ring.

6. Which of the following species is NOT an electrophile?

A. NH3
B. Br2
C. HBr
D. AlCl3

- 35 -
TUTORIAL 12: INTRODUCTION TO ORGANIC CHEMISTRY

7. Which of the following free radical is the most stable?

A CH 3

B
CH3CH 2
C (CH 3 )2 CH

D
CH3

Choose the most appropriate answer from the options given below.

SUMMARY OF OPTIONS
A B C D
I only I and II only II and III only I, II and II

8. Which of the following species is/are nucleophile(s)?

I OH
II H2O
III R3C

9. Which of the following compound(s) is/are optically active?

I (Cl)CH2CH2CH3
II CH3CH(OH)CH2CH3
III CH3CH(NH2)COOH

10. A pair of enantiomers has the following characteristic:

I They are non-mirror images.
II They are stereoisomers.
III Each enantiomer rotates plane-polarised light in opposite direction of the other.

- 36 -