Question

1. Using the reaction of 2-chloro-1-methylcyclohexane with hydroxide ion, give the mechanism of Sn1 substitution.  Complete the question as in question 1

2. Show how you might synthesise the following compounds given the indicated starting materials and anything else you need.  In other words, show the reactions that would lead from starting materials to products.  Assume that you can purify the products of each reaction.  A synthesis may require more than one reaction (products of one reaction are used as starting materials in the next).

(a) 2-bromobutane from butane and bromine

(b) 2-butanol from butane, bromine and sodium hydroxide

Answer 1

Question 1) The reaction of 2-chloro-1-methylcyclohexane with hydroxide ion gives following product ОН NaOH 2-Chloro-1-methyl Cyclohex ane Mechanism он OH Nucle ophilic Loss of Hydride Shift leaving group attack Step- Step-ll Step-ll The first step involves loss of leaving group to generate a secondary carbocation which gets rearranged to more stable tertiary carbocation by hydride shift. In the last step nucleophilic attack take place on tertiary carbocation to form alcohol. Question 2) a) 2-bromobutane from butane Br2 Light Br Synthesis of 2-bromobutane can be done using Br2 in presence of UV light b) 2-butanol from butane, bromine and Sodium hydroxide Br2 NaOH Light ОН Br Butane 2-butanol