7) synthesize t-butyl isobutyl ether from isobutylene IX. Purification (8 points

Question

7) synthesize t-butyl isobutyl ether from isobutylene

IX. Purification (8 points) Indicate the best method to purify the following mixture. A mixture of 2-methyiphenol, benzylalcohol and benzoic acid were purified into three pure substances using the following scheme. Indicate what species are present in each container (box). Be sure to indicate the charged species present. VII. Multistep Synthesis (16 points) Suggest suitable reagents and conditions to carry out the indicated transformations in a multistep synthesis indicate all intermediates formed. a) Synthesize t-butyl isobutyl ether from isobutylene (2-methyipropene). b) Synthesize meta-bromoaniline from benzene. VIII. Mechanism (9 points) Draw the complete correct mechanism for the nucleophilic substitution of bromobenzene by potassium amide. Include all formal charges and electrons.

Explanation / Answer

(a)

First add sulfuric acid and then water to isobutylene. This breaks the double bond and creates an alcohol. In a separate reaction, take isobutylene and react it with HBr and ROOR. Use HBr together with a radical catalyst, such as a dialkylperoxide, to make an alkyl halide from an alkene when you want to attach the Br to the less substituted carbon of the double bond. React the alcohol synthesized in the first part with NaH and then add the product from the second reaction. Use NaH to make an alkoxide for use as one of the reacting partners in the Williamson ether synthesis.

(b)

React benzene with 1. HNO3, H2SO4 2. Br2, FeBr3 3. H2, Pd-C

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