Organic Chemistry: Halogenoalkanes (Edexcel International AS Chemistry)

Ammonia reacts with 1‐chlorobutane.

State the type and mechanism of this reaction.

A student drew the first step of the mechanism for the reaction.

(2)

(3)

The reactions of ammonia and of hydroxide ions with halogenoalkanes are similar.

Compare the rate of reaction of ammonia with 1‐chlorobutane and with 2‐bromo‐2‐methylpropane.
Justify your answer.

This question is about halogenoalkanes.

The rates of hydrolysis of 1-chloropropane, 1-bromopropane and 1-iodopropane in reactions with aqueous silver nitrate solution were compared.

(1)

(2)

The equation for the hydrolysis of 1-chloropropane by aqueous hydroxide ions is shown.

CH₃CH₂CH₂Cl + OH⁻ → CH₃CH₂CH₂OH + Cl⁻

Give the mechanism for this hydrolysis.
Include curly arrows, and relevant dipoles and lone pairs.

The boiling temperatures of some halogenoalkanes are shown.

Explain the trend in boiling temperature of these halogenoalkanes by comparing the intermolecular forces involved.

Detailed explanations of the forces involved are not required.

In another experiment, 2-bromobutane is heated with ethanolic potassium hydroxide and an elimination reaction occurs.

Draw the skeletal formulae of the three possible organic products, giving their names.

The compound DMAA was originally synthesised as a decongestant.

A suggested synthetic route for DMAA is shown.

(1)

(1)

(4)

DMAA is only slightly soluble in water but dissolves readily in hydrochloric acid to form an aqueous solution.

(3)

(3)