1.

(a) Write the equations for the steps involved in the S_(N)1 mechanism of hydrolysis of 2-bromo 2 methyl propane. (b) (i) Name the product formed for the reaction of isopropyl iodide on alcoholic KOH. (ii) What is the condition to be satisfied for a compound to be chiral?(c) What is racemic mixtures?

Answer»

Solution :(a)The reaction between tert-butyl bromide and hydroxide ion gives tert-butyl alcohol. The rate of reaction depends only on the concentration of tert-butyl bromide. Hence it is a nucleophillic first order substitution reaction. `H_(3)C-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-Br+ OH^(-) to H_(3)C-underset(CH_(3))underset(|)overset(CH_(3))overset(|)(C)-OH+Br^(-)`
MECHANISM:
STEP 1: Polarised C- Br undergoes cleavage to produce planar CARBONATION.

Step 2: The CARBOCATION is then attacked by nucleophile `(OH^(-))` on either side to FORM tert-butyl alcohol. .
(b)(i) Propene
(ii) Compound should contain chiral carbon atom [Carbon bonded to four different groups/atoms] and its mirror image is non-superimposable.
(c)Equimolar mixture of d and / isomers.


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