11.1 Introduction to Organic Chemistry, Set A Answer Key To print: Ctrl + P, paper A4, margins Default.
Learners' AlleyDesigned by Khow Willard
11.1

Introduction to Organic Chemistry

Set AAnswer key
A

From the lesson

10 marks
1

88 (one more CH2, +14).[1]

Both have the same functional group, –OH, which decides the reactions.[1]

2

CH3: sp3, CH and CH2: sp2[1]

6 C–H + 2 C–C = 8 σ, 1 π[1]

3

An electron pair donor, with a lone pair of electrons.[1]

4

sp2, 120°.[1]

5

The bonding electrons are shared equally, one to each atom, forming two free radicals.[1]

6

Nucleophilic substitution.[1]

7

It has one chiral centre and one C=C bond that shows cis–trans isomerism.[1]

Number of stereoisomers = 22 = 4[1]

B

Practice

20 marks
8

C4-methylhex-2-ene[1]

2-methylhex-2-ene does not exhibit stereoisomerism.

3-methylhex-2-ene and 5-methylhex-2-ene have only cis and trans isomers: number of stereoisomers = 21.

4-methylhex-2-ene has 22 = 4 stereoisomers.

9
(a)
3-chloropent-1-ene[1]
(b)
5,6-dihydroxyheptan-3-one[1]
(c)
4-ethyl-3,6-dimethyloctane[1]
(d)
2-ethyl-1,1-dimethylcyclobutane[1]
10
(a)
addition or reduction or catalytic hydrogenation[1]
(b)
nucleophilic addition[1]
(c)
elimination[1]
(d)
free radical substitution[1]
(e)
elimination or dehydration[1]
(f)
hydrolysis[1]
11

Cis-trans isomerism occurs when there are 2 different substituents attached to each of the two carbon atoms of a C=C bond, due to its restricted rotation.[1]

Enantiomerism occurs when a molecule is chiral with no plane of symmetry, hence giving rise to a pair of isomers that are non-superposable mirror images. These compounds can rotate the plane of polarised light.[1]

12
(a)

hex-3-ene: geometric (cis-trans) isomerism[1]

  [1]

(b)

2-bromobutane: optical isomerism[1]

 |  [1]

NoteShow a tetrahedral shape about the chiral carbon, draw the dash and wedge bonds clearly, and draw the mirror plane between the mirror images.

13

Molecules A, B and C are stereoisomers. Each molecule has 2 chiral carbon atoms.[1]

As molecules A and B have no plane of symmetry, they are chiral and exist as a pair of enantiomers, which are non-superimposable mirror images. Each enantiomer is optically active and rotates plane polarised light by an equal magnitude but in opposite directions.[1]

Molecule C, which has a plane of symmetry, is achiral (a meso compound). It is superimposable on its mirror image and is optically inactive.[1]