The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry

1. Complete the table

Name

Structure

Examples & isomers Structural

formula
C4H10

Alkanes

C-C (all single

bonds)

Alkenes

C=C (double
bonds)

C3H6

Alcohols

C-OH

C4H10O

C4H8O

Aldehydes

Display formula

HC
H

Ketones

C4H8O

R-C-R
Acids

C4H8O2

R - C - OH
Esters

C4H8O2

R - C - OR
C3H9N (three types)

Amines
R-NH2

- Functional Groups - Structures and Nomenclature

Name
Alkanes
Alkenes

Structure

Examples & isomers Name

Ending
C4H10
Root
name

IUPAC Name

C3H6
-ene

Alcohols

C4H10O
-ol

Aldehydes

C4H8O
-al

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry
C4H8O

Ketones

-one
C4H8O2

Acids

-oic acid
Esters

C4H8O2

--yl

Amines

C3H9N (three types)

-oate
-yl
amine

2. Name the following compounds and write their skeletal formula and structural
formula.

(a)
H

CH3 H

CH3 H

(b)
Br

H
C
H

(c)
H
H

(d)
H
H

Cl

H
H

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry

3. Write the display formula of the following compounds.

a. CH3CH(CH3)CH3

b. CH3CHBrCH2Br

c. CH2=CHCH2CH3

d. CH3CH=C(CH3)CH3

4. Write the structural formula of the following compounds.

a. Methylbutane ..
b. but-1-ene
c.

3-ethyl,2-methylhex-1-ene.

d. 3-chlorobut-1-ene ..
e. 1,1-dichloropropane..
f.

2,2,4-trimethylheptane

g. pent-2-ene

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry

5. Name the following organic compounds:

O
C

CH3

CH2

CH

CH3

CH3

H
C 2H 5

N
C 2H 5

6. Draw displayed formulae for the following compounds:

a. 2-hydroxyethanamide

b. ethanoic butanoic anhydride

c. ethyl 2-hydroxypropanoate

d. N-methylbutanamide

e. N- methyl, N-ethyl, 2-aminobutane

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry

f. sodium 2-hydroxyethanoate

7.

8. P, Q and R have the molecular formula C6H12

All three are branched-chain molecules and none is cyclic.
P can represent a pair of optical isomers.
Q can represent a pair of geometrical isomers.
R can represent another pair of geometrical isomers different from
Q.
Draw one possible structure for one of the isomers of each of P, Q and R.
Structure of P

Structure of Q

Structure of R

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry
9. What is meant by a chiral compound?
................................................................................................................................
................................................................................................................................
(a) But-2-ene, CH3CH=CHCH3, exists as geometric isomers.
(i) Draw the geometric isomers of but-2-ene.

(ii) Explain how geometric isomerism arises.

......................................................................................................................
......................................................................................................................
(b) (i) Draw the structural formula of a compound which is an isomer of but-2-ene
but which does not show geometric isomerism.

(ii) Explain why the isomer drawn in (i) does not show geometric isomerism.
......................................................................................................................
......................................................................................................................
10. Name the alkene CH3CH2CH=CH2
........................................................................................................................
(i) Explain why CH3CH2CH=CH2 does not show geometrical isomerism.
........................................................................................................................
........................................................................................................................
(ii) Draw an isomer of CH3CH2CH=CH2 which does show geometrical
isomerism.

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry
(iii) Draw another isomer of CH3CH2CH=CH2 which does not show
geometrical isomerism.

11. Four of the structural isomers of C4H10O are alcohols. One of these isomers is
butan-2-ol.
a. Draw the structural formula E of two other alcohols with molecular formula
C4H10O and name each of these isomers.
Diagrams
Isomer 1
Isomer 2

Name of isomer 1

Name of isomer 2

12. a) Explain the following terms and give an example of each.

i) Electrophile

ii) Nucleophile

.
iii) Free radical

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry
b) Write the balanced equation to illustrate:
i) Electrophilic addition

ii) Nucleophilic substitution

iii) Free-radical substitution

c) A chemical bond can be broken either by homolytic fission or by heterolytic

fission. Explain , with the aid of suitable equations, what you understand by
the terms homolytic fission and heterolytic fission.

13. But-2-ene and butan-2-ol both exhibit stereoisomerism.

a) Explain what is meant by the term stereoisomerism

b) Name the type of stereoisomerism shown by but-2-ene and butan-2-ol.

c) Using appropriate type of formulae, illustrate your answers to b for but-2-ene

and butan-2-ol. Draw to structures of each type of isomerism.

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry

14. Draw all the possible structural isomers of C5H11Br (there are 8 in total). Label the
isomers A H and name them.
a) Identify two molecules which are positional isomers.

b) Identify two molecules which are chain isomers.

c) Identify two molecules which are chiral and draw the two optical isomers of
each. Explain briefly how they could be distinguished.

15. a) Draw the two possible structures of a molecule with molecular formula C4H8O2
and containing a carboxylic acid group. Name both of the isomers.

b)Draw four possible structures of molecules with the same molecular formula
but containing a different functional group. Name the functional group and the
molecules containing it. What is the type of isomerism shown between these
molecules and the molecules drawn in (a)?

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry

16. The alkanes form an homologous series of hydrocarbons. The first four straightchain alkanes are shown below.
methane
CH4
ethane
C2H6
propane
CH3CH2CH3
butane
CH3CH2CH2CH3

a) State what is meant by the term hydrocarbon.

b) Each homologous series has its own general formula. State two other
characteristics of an homologous series.
......................................................................................................................
......................................................................................................................
......................................................................................................................
c) Branched-chain structural isomers are possible for alkanes which have more
than three carbon atoms.
(i) State what is meant by the term structural isomers.
....................................................................................................................
....................................................................................................................
...................................................................................................................
(ii)

Name the two isomers of hexane shown below.

Name .................................................................

Name ...................................................................

10

The Oxford School, Dubai

AS Chemistry Workbook
Topic Organic chemistry
(iii)Give the structures of two other branched-chain isomers of hexane.
Isomer 3
Isomer 4

d) A hydrocarbon, W, contains 92.3% carbon by mass. The relative molecular

mass of W is 78.0
(i)
Calculate the empirical formula of W.

(iii)

Calculate the molecular formula of W.

.............................................................................................................
.............................................................................................................

11