Given that radical chlorination of (R)-2-chloropentane yields 2,4-dichloropentane in low yield. The number of stereoisomers formed, in what ratio and which of them are optically active are to be stated. Concept introduction: Whenever a new chiral centre is created in an optically active reactant in a reaction, diasteoisomers are produced. These diastereoisomers are usually obtained in unequal proportions as the approach of the reagent from backside is usually hindered. The diastereoisomers will be optically active if they are non superimposable on their mirror images and optically inactive if they are superimposable on their mirror images. To state: The number of stereoisomers formed in the reaction in which radical chlorination of (R)-2-chloropentane yields 2,4-dichloropentane in low yield. The ratio in which they are formed and which of them are optically active are also to be stated.

Question

1, part A) In the reaction below, draw all of the possible products. 1, part B) For all the products you have drawn, draw their corresponding carbocations while also identifying if each is 1o/2o/3o carbocation. In addition, starting from alkene - provide complete accurate arrow-pushing mechanisms of each carbocation formation. 1, part C) In part B, circle the carbocation which is *most* stable, indicate why.

Answer 1

Question

Chapter 10.SE, Problem 39AP

Interpretation Introduction

Interpretation:

Given that radical chlorination of (R)-2-chloropentane yields 2,4-dichloropentane in low yield. The number of stereoisomers formed, in what ratio and which of them are optically active are to be stated.

Concept introduction:

Whenever a new chiral centre is created in an optically active reactant in a reaction, diasteoisomers are produced. These diastereoisomers are usually obtained in unequal proportions as the approach of the reagent from backside is usually hindered. The diastereoisomers will be optically active if they are non superimposable on their mirror images and optically inactive if they are superimposable on their mirror images.

To state:

The number of stereoisomers formed in the reaction in which radical chlorination of (R)-2-chloropentane yields 2,4-dichloropentane in low yield. The ratio in which they are formed and which of them are optically active are also to be stated.

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