b) Write the chemical equation for nucleophilic substitution reaction of 2-bromo-2-cyclopropylpentane.

Name the type of nucleophilic substitution reaction that involved. Write the mechanism for the
reaction.

𝐻2 𝑂𝐻/𝐻3 𝑂

H𝐻3 𝐶 − 𝐶 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3 𝐻3 𝐶 − 𝐶 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3 + 𝐵𝑟 −

Br OH

Type of nucleophilic substitution reaction is 𝑆𝑁1 reaction.

Mechanism :

Step 1: formation of carbocation

slow
𝐻3 𝐶 − 𝐶 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3 𝐻3 𝐶 − 𝐶 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3 + 𝐵𝑟 −

Br

Step 2 : nucleophilic attack

fast
𝐻3 𝐶 − 𝐶 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3 + O𝐻 − 𝐻3 𝐶 − 𝐶 − 𝐶𝐻2 − 𝐶𝐻2 − 𝐶𝐻3

OH
ii) Write the chemical equations for nucleophilic substitution reaction of 1-chloropropane. Name the
type of nucleophilic substitution reaction that involved. Write the mechanism for the reaction.

Cl OH

𝐻2 𝐶 − 𝐶𝐻2 − 𝐶𝐻3 + 𝑁𝑎𝑂𝐻 𝐻2 𝐶 − 𝐶𝐻2 − 𝐶𝐻3 + 𝑁𝑎𝐶𝑙

Type of nucleophilic substitution reaction is 𝑆𝑁2 reaction.

𝐶𝐻2 𝐶𝐻3 𝐶𝐻2 𝐶𝐻3

𝐶𝐻2 𝐶𝐻3 slow fast
𝑂𝐻 − C Cl 𝐻𝑂 C Cl HO C + C𝑙 −
H
H H H H H
3. a) i) Propose a synthetic route to produce benzoic acid from benzene via Grignard Reagent.

+ 𝐶𝐻3 𝐶𝑙