PART B

1.
i ) State two types of bond cleavage that can occur in a covalent bond. Compare them by
explaining how these cleavages occur and the species formed.

HOMOLYTIC CLEAVAGE HETEROLYTIC CLEAVAGE

Occurs in a non-polar bond Occurs in a polar bond involving unequal sharing of

involving two atoms of similar electron pair between two atoms of different
electronegativity. electronegativity.

A single bond breaks A single bond breaks unsymmetrically both the bonding
symmetrically into two equal electrons the bonding electrons are transferred to the
parts, leaving each atom with more electronegative atom.
one unpaired electron.

nvvFormed tree radicals. Formed cation and anion.

ii ) Complete the following reaction equation and discuss the bond cleavage involved in the
terms of intermediate species.

Type of bond cleavage: Heterolytic cleavage

- For HCl, chlorine is more electronegative than hydrogen.
- H-Cl bond breaks unsymmetrically in which the chlorine atom attracts bonding pair
electrons towards it, and produce H+ and Cl- ion.
- NH3 has a lone pair of electron on the nitrogen atom which tends to attack the H+ ion
to form NH4+ ion.
2.
i ) Arrange the following carbocations in order of increasing stability. Explain.

 The stability of carbocation increases with the number of the alkyl groups
present which showed methyl carbocation is less stable compared to tertiary
carbocation because it has the least number of alkyl group present while the
tertiary carbocation has the most number of alkyl group present.

3.
i ) State the 4 main types of organic reactions and explain each type briefly.

Addition reaction – A reaction in which atoms or groups add to adjacent atoms of a multiple
bond.
 Electrophilic addition reaction
Electrophilic addition is a reaction between an electrophile and nucleophile, adding to double
or triple bonds. An electrophile is defined by a molecule with a tendency to react with other
molecules containing a donatable pair of electrons.
Example : Alkenes and alkynes compound.
  Nucleophilic addition reaction
A nucleophilic addition reaction is a chemical compound with an electron-deficient or
electrophilic double or triple bond, a π bond, reacts with electron-rich reactant, termed a
nucleophile, with disappearance of the double bond and creation of two new single, or σ,
bonds.
Example : Carbonyl compound.

Substitution reaction - A reaction in which an atom or group in a molecule is replaced by

another atom or group.

 Free radical substitution reaction

A reactions in which one atom in a molecule is replaced by another atom or group of atoms.
Free radical substitution often involves breaking a carbon-hydrogen bond in alkanes.
  Electrophilic substitution reaction
A chemical reactions in which an electrophile displaces a functional group in a compound,
which is typically, but not always, a hydrogen atom. ( the aromatic nucleus has high electron
density, thus it is nucleophilic and is prone to electrophilic attack.)
Example : Aromatic compounds

 Nucleophilic substitution reaction ( Typical reaction of saturated organic

compounds bearing polar bond as functional group.)
Example : Haloalkane with alcohol.

Elimination reaction – An atom or groups are removed from adjacent carbon atoms of a
molecule to form multiple bonds. Will result in formation of unsaturated molecules.
Rearrangement reaction – A reaction in which atoms or groups in a molecule change
position it occurs when a single reactant reorganizes the bonds and atoms.

ii ) Name the types of reaction for steps A,B,C and in the following scheme.

Step Types of reaction

A Nucleophilic substitution reaction
B Elimination reaction
C Electrophilic addition reaction
D Rearrangement reaction
4. Draw the structure of paracetamol ( acetaminophen ) and identify all the functional groups
present.

Drawing Functional group present

carboxamide

Benzene
ring

Hydroxyl
5. 2-methylbutanal is an aldehyde that can exists as stereoisomers.

i) Identify the chirality centre using asterisk (*)

2-methylbutanal
ii) Draw a pair of enantiomers for the compound using 3-dimensional structural
formula.
References
(n.d.).
- Chemistry Study Guide. (n.d.). Chemistry Unit Matriculation Kedah.
- Clark, J. (2000). What is nucleophilic substitution. Retrieved from Chemguide:
https://www.chemguide.co.uk/mechanisms/nucsub/whatis.html
- Organic Reactions. (2019, November 24). Retrieved from Wikipedia:
https://en.wikipedia.org/wiki/Organic_reaction
- Z., E. (2014, November 24). Homolytic v Heterolytic Cleavage. Retrieved from Socratic Q
& A: https://socratic.org/organic-chemistry-1/radical-reactions/homolytic-v-
heterolytic-cleavage
 KOLEJ MATRIKULASI KEDAH
SESI 2019/2020
SK025
INTRODUCTION TO ORGANIC CHEMISTRY

NAMA : NURUL SAHIRA BINTI MOHD YUSOFF

KELAS : S4T5
NO. MATRIK : MS1918123920
NAMA PENSYARAH : SIR ABDUL BASET BIN ABDULLAH