How does the diethyl ether react with the following reagents?
a) $O_{2} /$ long contact
b) $H I$ is excess
c) $P C l_{5}$
d) $H O H$

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Solution

(a) When diethyl ether is exposed to oxygen for a long time, if forms peroxide. These peroxides are unstable and decomposes violently with explosion on heating. Hence, ether should not be evapourated to dryness.
$C_{2} H_{5} - O - C_{2} H_{5} (o) \to (C_{2} H_{5})_{2} O_{2} D i e t h y l p e r o x i d e$
(b)When diethyl ether reacts with excess hot concentrated hydroidic acid alkyl iodides are formed.
$C_{2} H_{5} - O - C_{2} H_{5} + 2 H I \to 2 C_{2} H_{5} I E t h y l i o d i d e + H_{2} O$
(c) When diethyl ether reacts with $P C l_{5}$ , ethyl chlorides are produced along with $P O C l_{3}$ .
$C_{2} H_{5} - O - C_{2} H_{5} + P C l_{5} \to 2 C_{2} H_{5} C l E t h y l c h l o r i d e + P O C l_{3} P h o s p o n y l c h l o r i d e$
(d) When diethyl ether is boiled with water in the presence of dil, $H_{2} S O_{4}$ , hydrolysis takes place to form ethyl alcohols.
$C_{2} H_{5} - O - C_{2} H_{5} + H O H d i l . H_{2} S O_{4} \to 2 C_{2} H_{5} O H E t h y l a l c o h o l$ .

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