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

4-43 For each alkane, 1. draw all the possible monochlorinated derivatives. 2. determine whether free-radical chlorination would be a good way to make any of these monochlorinated derivatives. (Will the reaction give mostly one major product?) 3. which monobrominated derivatives could you form in good yield by free-radical bromination? (a) cyclopentane (c) 2-methylpentane (b) methylcyclopentane (d) 2,2,3,3-tetramethylbutane

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

4-43 For each alkane, 1. draw all the possible monochlorinated derivatives. 2. determine whether free-radical chlorination would be a good way to make any of these monochlorinated derivatives. (Will the reaction give mostly one major product?) 3. which monobrominated derivatives could you form in good yield by free-radical bromination? (a) cyclopentane (c) 2-methylpentane (b) methylcyclopentane (d) 2,2,3,3-tetramethylbutane

3. Two substitution products result from the reaction of 3-chloro-3-methyl-1-butene with sodium acetate (CH:CO2 Na*) in acetic acid under SN1 conditions. Identify the products. (Hint: Resonance form) Please predict the products in the following reactions. (Hint: Stereochemistry!!) CH,CH3 SN2 conditions + НО- CH3 Br (S)-2-bromobutane CH,CH3 SN1 conditions + H,O CH3 Br (S)-2-bromobutane 4.

The two alkenes below react with HI at different rates. CH3CH=CHCH3 and CH₂=CH₂ Draw the structural formula of the MAJOR product formed by the alkene having the HIGHER reaction rate. • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • In cases where there is more than one answer, just draw one. TAYY [ ] در ChemDoodle Ⓡ