The alkyl beromide shown is prepared by treating (S)-2-pentanol with PBr 3 . The name of the alkyl bromide and its stereochemistry whether R or S are to be stated. Further whether there is any change in stereochemistry during the course of the reaction is also to be stated. Concept introduction: The alkyl halides are named using the following guidelines. The longest continuous carbon chain in the molecule is chosen. The chain is numbered from the end which gives lowest number to the substituent either halo or alkyl group present. For assigning the configuration as R or S, the four groups attached to the chiral carbon are arranged in the order of preference based on the sequence rules. The molecule is viewed by orienting the molecule in such a way that the group of lowest ranking points away from the observer. If the arrangement of the groups of first, second and third ranking (1->2->3-) is clockwise R configuration is assigned. If their arrangement is anti-clockwise then S configuration is assigned. If both the reactants and products of a reaction have same configuration the reaction is said to occur with retention in stereochemistry. If they have different configurations the reaction is said to occur with inversion in stereochemistry.

Question

Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?

Answer 1

Question

Chapter 10.SE, Problem 16VC

Interpretation Introduction

Interpretation:

The alkyl beromide shown is prepared by treating (S)-2-pentanol with PBr₃. The name of the alkyl bromide and its stereochemistry whether R or S are to be stated. Further whether there is any change in stereochemistry during the course of the reaction is also to be stated.

Concept introduction:

The alkyl halides are named using the following guidelines. The longest continuous carbon chain in the molecule is chosen. The chain is numbered from the end which gives lowest number to the substituent either halo or alkyl group present.

For assigning the configuration as R or S, the four groups attached to the chiral carbon are arranged in the order of preference based on the sequence rules. The molecule is viewed by orienting the molecule in such a way that the group of lowest ranking points away from the observer. If the arrangement of the groups of first, second and third ranking (1->2->3-) is clockwise R configuration is assigned. If their arrangement is anti-clockwise then S configuration is assigned.

If both the reactants and products of a reaction have same configuration the reaction is said to occur with retention in stereochemistry. If they have different configurations the reaction is said to occur with inversion in stereochemistry.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Which stereoisomer of 3-hexene forms (3S,4S)-4-bromo-3-hexanol and (3R,4R)-4-bromo-3-hexanol when it reacts with Br2 and H2O?

1. Predict the elimination products of the following reactions. When two alkenes are possible, predict which one will be the major product. Explain your answers, showing the degree of substitution of each double bond in the products. 2. Which of these reactions are likely to produce both elimination and substitution products? (a) 2-bromopentane +NaOCH3 (b) 3-bromo-3-methylpentane +NaOMe(Me= methyl, CH3) (c) 2-bromo-3-ethylpentane +NaOH (d) cis-1-bromo-2-methylcyclohexane +NaOEt (Et= ethyl, CH2CH3)

In an advanced synthetic chemistry experiment, a researcher prepares a compound, ZY-7, by reacting a ketone (C5H10O) with hydroxylamine (NH2OH), followed by heating in the presence of an acid catalyst. The resulting compound, ZY-7, is then treated with a solution of sodium nitrite (NaNO2) and hydrochloric acid (HCl) at low temperature. Identify the class of compound that ZY-7 most likely belongs to after this series of reactions." A) Amide B) Oxime C) Nitro compound D) Diazonium salt E) Ester Don't use chatgpt please provide valuable answer