ALKYL HALIDES ASSESSMENT 1

INDEX NUMBER : UHAS20191097

QUESTION 1

Discuss in not more than 200 words the pharmaceutical importance of

Organohalogens.

Organohalogen compounds refer to compounds that contain at least one halogen atom
bonded to a carbon. Many Organohalogen compounds are important industrial
chemicals whiles other natural Organohalogens can be used in the production of
drugs .eg. forazoline A was isolated from marine Actinomadura sp.

Organohalogens are widely used in the pharmaceutical industry to produce drugs

.Many drugs require Organohalogens to be used as effective therapeutic agents
.Example, Rafoxanide is a salicylanilide which is used as an antihelmintic,Closantel
( C22H14Cl2I2N2O2 ) is also an active antiparasitic agent. Ceclor (C15H14ClN3O4S ) ,
Lorabid( C16H16ClN3O 4)) ) Toremifene etc. are all examples of drugs derived from
Organohalogens .Organohalogens such as Ethyl chloride and sevoflurane are also
used as anesthetics

Alkyl halides have also contributed to human health through their use as
insecticides.eg,

Dichlorodiphenyltrichloroethane (DDT)

Rafoxanide

2.A) Identify and name the product(s) on the dehydrohalogenation of 2-bromobutane.

Dehydrohalogenation involves removal of the halogen atom together with a hydrogen

atom from a carbon adjacent to the one bearing the halogen

In the dehydrohalogenation of 2 – bromobutane, the following products will be

produced
1. 1-Butene 2. Cis- CH3CHCHCH3 / cis 2 – butene 3.trans- CH3CHCHCH3/ trans 2-
butene

B) What rule predicts the proportions of the products ?

Zaitsev’s rule

3. Using a five carbon secondary alkyl halide ,explain the concept of SN1 reaction
(not more than 400 words)

SN1 stands for substitution nucleophilic unimolecular reactions. The term

unimolecular means there is only one molecule involved in the transition state of the
rate-limiting step. The first step which involves the unimolecular dissociation of the
alkyl halide to form a carbocation as the key intermediate, is the rate determining step.
SN1 reactions follows the first order kinetics ,i.e. the rate of the reaction depends on
the concentration of one molecule ( the alkyl halide)

The SN1 reaction follows a step by step process in which first a carbocationis formed
from the removal of the leaving group .then the carbocation is attacked by the
nucleophile. Finally, the deprotonation of the protonated nucleophile takes place to
give the required product

For example, hydrolysis of the secondary alkyl bromide 2-bromo-3-methylbutane

yields the rearranged tertiary alcohol 2-methyl-2-butanol as the only substitution
product

The first step in this reaction involves the rate determining ionization of the substrate
(2-bromo-3-methylbutane) to the secondary carbocation ( 1,2-Dimethylpropyl
cation ) followed by a hydride shift to a more stable tertiary carbocation (1,1-
Dimethylpropyl cation) .

The tertiary carbocation (1,1-Dimethylpropyl cation) then reacts with water which
acts as weak nucleophiles ,the intermediate product is then deprotonated to
yield 2-methyl-2-butanol

Clearly, the steric crowding that influences reaction rates in SN2 processes plays no
role in SN1 reactions. The order of alkyl halide reactivity in SN1 reactions is the same
as the order of carbocation stability: the more stable the carbocation, the more reactive
the alkyl halide.

REFERENCES

1. Solomons T.W & Fryhle C Organic chemistry 2011 (10th ed)

John Wiley & Sons, Inc. page 256 – 258

2. Carey F.A (2000)
The McGraw-Hill Companies Inc, USA
Page 319&320