(a) Interpretation: The mechanism that accounts for the formation of the mixture of the products in a given reaction is to be drawn. Concept introduction: Electrophilic addition of the molecular chlorine into but-2-ene gives anti-addition of the molecular chlorine via the formation of the chloronium ion as an intermediate. Under similar conditions, molecular chlorine undergoes both syn and anti-addition to (E)-1-phenylprop-1-ene that produces the isomer plus enantiomers. In order to show both syn and anti-addition, the carbocation like intermediate must be generated. Hence, this electrophilic addition proceeds via formation of stable benzylic carbocation intermediate instead of the formation of chloronium ion. As this reaction leads to formation of two different benzylic carbocation intermediates, the reaction yields four different products which consists of two pairs of enantiomers.

Question

You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products: xi 1. ☑ 2. H₂O хе i Draw the missing reagent X you think will make this synthesis work in the drawing area below. If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank. Click and drag to start drawing a structure. There is no reagent that will make this synthesis work without complications. : ☐ S ☐

Answer 1

Question

Chapter 12, Problem 12.56P

Interpretation Introduction

(a)

Interpretation:

The mechanism that accounts for the formation of the mixture of the products in a given reaction is to be drawn.

Concept introduction:

Electrophilic addition of the molecular chlorine into but-2-ene gives anti-addition of the molecular chlorine via the formation of the chloronium ion as an intermediate. Under similar conditions, molecular chlorine undergoes both syn and anti-addition to (E)-1-phenylprop-1-ene that produces the isomer plus enantiomers. In order to show both syn and anti-addition, the carbocation like intermediate must be generated. Hence, this electrophilic addition proceeds via formation of stable benzylic carbocation intermediate instead of the formation of chloronium ion. As this reaction leads to formation of two different benzylic carbocation intermediates, the reaction yields four different products which consists of two pairs of enantiomers.

Interpretation Introduction

(b)

Interpretation:

The mechanism for the electrophilic addition of the molecular chlorine to the 1-phenylprop-1-ene is different from the one for but-2-ene is to be explained.

Concept introduction:

Electrophilic addition of the molecular chlorine into but-2-ene gives anti-addition of the molecular chlorine via the formation of the chloronium ion as an intermediate. Under similar conditions, molecular chlorine undergoes both syn and anti-addition to (E)-1-phenylprop-1-ene that produces the isomer plus enantiomers. In order to show both syn and anti-addition, the carbocation like intermediate must be generated. Hence, this electrophilic addition proceeds via formation of stable benzylic carbocation intermediate instead of the formation of chloronium ion. As this reaction leads to formation of two different benzylic carbocation intermediates, the reaction yields four different products which consists of two pairs of enantiomers.

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