In each case, show how you would synthesize the chloride, bromide, and iodide from the corresponding alcohol.

(a) 1-halopropane (halo = chloro, bromo, iodo)

(b)1-halo-2-methylcyclopentane

(c)1-halo-1,3-dimethylcyclohexane

(d)2-halo-1,3-dimethylcyclohexane

An organic compound that contains at least one hydroxyl group is said to be an alcohol compound.Primary and secondary alcohol undergoes chlorination, bromination and iodination upon reaction with SOCl₂, PBr₃ and P/I₂.

Propan-1-ol is a primary alcohol that contains three carbon atoms and one hydroxyl group.

Propan-1-ol is reacted with SOCl₂ forming 1-chloropropane.

Formation of 1-chloropropane

Propan-1-ol is reacted with PBr₃ forming 1-bromopropane.

Formation of 1-bromopropane

Propan-1-ol is reacted with P/I₂ forming 1-iodopropane.

Formation of 1-iodopropane

Secondary alcohol,2-methyl cyclopentan-1-ol, contains one methyl group at the second position and one alcohol group attached to the first carbon. Used to synthesize 1-halo-2-methylcyclopentane.

2-methyl cyclopentan-1-ol is treated with SOCl₂ forms 1-chloro-2-methylcyclopentane.

Formation of 1-chloro-2-methylcyclopentane

2-methyl cyclopentan-1-ol is treated with PBr₃ forming 1-bromo-2-methylcyclopentane.

1-bromo-2-methylcyclopentane

2-methyl cyclopentan-1-ol is treated with P/I₂ forms 1-iodo-2-methylcyclopentane.

1-iodo-2-methylcyclopentane

Tertiary alcohol, 1, 3-dimethyl cyclohexan-1-ol is used to synthesize 1-halo-1, 3-dimethylcyclohexane. Tertiary alcohol undergoes halogenation via the S_N1 Mechanism upon reaction with strong acids, like HCl, HBr and HI.

1, 3-dimethyl cyclohexan-1-ol is treated with HCl form 1-chloro-1, 3-dimethylcyclohexane.

Formation of 1-chloro-1, 3-dimethylcyclohexane

1, 3-dimethyl cyclohexan-1-ol is treated with HBr form 1-bromo-1, 3-dimethylcyclohexane.

Formation of 1-chloro-1, 3-dimethylcyclohexane

1, 3-dimethyl cyclohexan-1-ol is treated with HI form 1-iodo-1, 3-dimethylcyclohexane.

Formation of 1-chloro-1, 3-dimethylcyclohexane

Secondary alcohol, 1, 3-dimethyl cyclohexan-2-ol contains two methyl groups and one hydroxyl group. Used to synthesize 2-halo-1, 3-dimethylcyclohexane.

1, 3-dimethyl cyclohexan-2-ol is treated with SOCl₂ form 2-chloro-1, 3-dimethylcyclohexane.

Formation of 2-chloro-1, 3-dimethylcyclohexane

1, 3-dimethyl cyclohexan-2-ol is treated with PBr₃ form 2-bromo-1, 3-dimethylcyclohexane.

Formation of 2-bromo-1, 3-dimethylcyclohexane

1, 3-dimethyl cyclohexan-2-ol is treated with P/I₂ form 2-iodo-1, 3-dimethylcyclohexane.

Formation of 2-iodo-1, 3-dimethylcyclohexane