INSTRUCTIONS: Choose from the options A-E and explain briefly by illustrations the chemistry behind each answer. 1. Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic products. i. All the following parameters would affect the rate and kinetics of the reaction except A. Solvent medium B. Reaction temperature C. Reaction time D. Geometry and structure of the alkyl halide E. pH ii. What would be the major product when 2-iodopentane is involved in a dehydrohalogenation reaction? A. 2-iodo-1-pentene B. 2-pentene C. (E)-2-pentene D. (Z)-2-pentene E. Cis-2-pentene Preamble: A student chemist in an attempt to synthesise compound B from the aromatic aldehyde. iii. Predict the chemical name of compound B A. p-chlorobenzylamine B. 4-bromoaniline C. benzylamine D. p-chloronitrile E. p-chlorobenzaldehyde iv. What is the reaction name for the chemical transformation of A to B A. reductive amination B. catalytic reduction C. carbonyl dehydration D. Hofmann elimination E. Aldehyde rearrangement The attached image contains the scheme of the reaction carried out on the synthesis of compound B from the aromatic aldehyde.

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter20: Acidity And Pka Of Phenols
Section: Chapter Questions
Problem 11E
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INSTRUCTIONS: Choose from the options A-E and explain briefly by illustrations the chemistry behind each answer.

1.

Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic products. 

i. All the following parameters would affect the rate and kinetics of the reaction except

A. Solvent medium

B. Reaction temperature

C. Reaction time

D. Geometry and structure of the alkyl halide

E. pH

ii. What would be the major product when 2-iodopentane is involved in a dehydrohalogenation reaction?

A. 2-iodo-1-pentene

B. 2-pentene

C. (E)-2-pentene

D. (Z)-2-pentene

E. Cis-2-pentene

Preamble: A student chemist in an attempt to synthesise compound B from the aromatic aldehyde

iii. Predict the chemical name of compound B

A. p-chlorobenzylamine

B. 4-bromoaniline

C. benzylamine

D. p-chloronitrile

E. p-chlorobenzaldehyde

iv. What is the reaction name for the chemical transformation of A to B

A. reductive amination

B. catalytic reduction

C. carbonyl dehydration

D. Hofmann elimination

E. Aldehyde rearrangement

The attached image contains the scheme of the reaction carried out on the synthesis of compound B from the aromatic aldehyde. 

 

 

Expert Solution
Step 1

1. The rate of the reaction is mostly dependant on the temperature and out of the given options, D and B are the correct ones.

It is mentioned that the formation of the two products takes place thus the reactions follow the mechanism of the E1 (unimolecular elimination reaction).

Chemistry homework question answer, step 1, image 1

2.   The major product when 2-iodopentane is involved in a dehydrohalogenation reaction is C. (E)-2-pentene as shown in the image below-

Chemistry homework question answer, step 1, image 2

 

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