The mechanism for the addition of bromine water to cyclopentene and explanation regarding formation of enantiomer is to be stated. Concept introduction: The general steps for the formation of halohydrin are stated below: The first step is the attack of halide ion to form a halonium ion. The second step is the attack of water to opens the halonium ion. The last step is deprotonation to give the halohydrin product. Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions . Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene , whereas syn addition is the addition of atom from the same side. Enantiomers are the non-super imposable mirror image of each other. To determine: The mechanism for the addition of bromine water to cyclopentene and explanation regarding formation of enantiomer.

Question

(a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.

Answer 1

Question

Chapter 8.9, Problem 8.19P

Interpretation Introduction

Interpretation: The mechanism for the addition of bromine water to cyclopentene and explanation regarding formation of enantiomer is to be stated.

Concept introduction: The general steps for the formation of halohydrin are stated below:

The first step is the attack of halide ion to form a halonium ion.

The second step is the attack of water to opens the halonium ion.

The last step is deprotonation to give the halohydrin product.

Stereochemistry is defined as the arrangement of molecule in three dimensional and its impact on chemical reactions.

Anti stereochemistry is the addition of any atom from the opposite faces of the double bond of alkene, whereas syn addition is the addition of atom from the same side. Enantiomers are the non-super imposable mirror image of each other.

To determine: The mechanism for the addition of bromine water to cyclopentene and explanation regarding formation of enantiomer.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

(a) Draw the products (including stereoisomers) formed when 2methylhex-2-ene is treated with HBr in the presence of peroxides. (b) Draw the products (including stereoisomers) formed when (S)-2,4dimethylhex-2-ene is treated with HBr and peroxides under similar conditions.

Draw all of the substitution and elimination products formed from the given alkyl halide with each reagent: (a) CH3OH; (b) KOH. Indicate the stereochemistry around the stereogenic centers present in the products, as well as the mechanism by which each product is formed.

(a) What product(s) are formed when the E isomer of C6H5CH = CHC6H5 is treated with Br2, followed by one equivalent of KOH? Label the resulting alkene(s) as E or Z. (b) What product(s) are formed when the Z isomer of C6H5CH = CHC6H5 is subjected to the same reaction sequence? (c) How are the compounds in parts (a) and (b) related to each other?