a) When 3-bromo-2,3-dimethylpentane, (CH3)CH2CBr(CH3)CH2CH 3, reacts with aqueous potassium hydroxide, an alcohol is formed. (i) Name the type of reaction taking place and give the role of the reagent. Type of reaction ............................................................................................... Role of reagent ................................................................................................. (ii) Outline a mechanism for the reaction, showing clearly the structure of the alcohol formed. (b) When 3-bromo-2,3-dimethylpentane reacts with ethanolic potassium hydroxide, three structurally isomeric alkenes are formed. (i) Name the type of reaction taking place and give the role of the reagent. Type of reaction ............................................................................................... Role of reagent ................................................................................................. (ii) One of the reaction products is 2,3-dimethylpent-2-ene. Give the structure of this alkene and outline a mechanism for its formation. Structure of alkene Mechanism (iii) Give the structures and names of the other two alkenes which are also formed. Structure of second alkene Name ................................................................................................................. Structure of third alkene Name ...........................................

Chemistry
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Chapter1: Chemical Foundations
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(a) When 3-bromo-2,3-dimethylpentane, (CH3)CH2CBr(CH3)CH2CH 3, reacts with aqueous potassium
hydroxide, an alcohol is formed.
(i) Name the type of reaction taking place and give the role of the reagent.
Type of reaction ...............................................................................................
Role of reagent .................................................................................................

(ii) Outline a mechanism for the reaction, showing clearly the structure of the alcohol formed.

(b) When 3-bromo-2,3-dimethylpentane reacts with ethanolic potassium hydroxide, three structurally
isomeric alkenes are formed.
(i) Name the type of reaction taking place and give the role of the reagent.
Type of reaction ...............................................................................................
Role of reagent .................................................................................................
(ii) One of the reaction products is 2,3-dimethylpent-2-ene.
Give the structure of this alkene and outline a mechanism for its formation.
Structure of alkene
Mechanism
(iii) Give the structures and names of the other two alkenes which are also formed.
Structure of second alkene
Name .................................................................................................................
Structure of third alkene
Name ............................................................................................................

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