Research in the “unzipping” of poly(vinyl chloride) indicates that certain defects in the polymer contribute to the rate of unzipping. These defects are arrangements of atoms that are different from the arrangements in the repeating units shown in the condensed formula. Researchers have found that defects involving allylic chlorides and tertiary chlorides, specifically, promote the reaction. These observations from the mechanism for the “unzipping” of poly(vinyl chloride) is to be explained. Concept introduction: The “unzipping” of PVC follows E1 mechanism in acidic medium. So, the stability of the carbocation is a matter in this case. As the stability of the carbocation increases, the rate of E1 reaction increases. The process of cutting (scission) of the polymer to the corresponding monomer is known as unzipping. The stability order of carbocation is Primary < Secondary < Benzylic, allylic < Tertiary .

Question

For this question, if the product is racemic, input both enantiomers in the same Marvin editor. A) Input the number that corresponds to the reagent which when added to (E)-but-2-ene will result in a racemic product. Input 1 for Cl, in the cold and dark Input 2 for Oy followed by H₂O, Zn Input 3 for D₂ with metal catalyst Input 4 for H₂ with metal catalyst B) Draw the skeletal structure of the major organic product made from the reagent in part A Marvin JS Help Edit drawing C) Draw the skeletal structure of the major organic product formed when (2)-but-2-ene is treated with peroxyacetic acid. Marvin 35 Help

Answer 1

Question

Chapter 26, Problem 26.77P

Interpretation Introduction

Interpretation:

Research in the “unzipping” of poly(vinyl chloride) indicates that certain defects in the polymer contribute to the rate of unzipping. These defects are arrangements of atoms that are different from the arrangements in the repeating units shown in the condensed formula. Researchers have found that defects involving allylic chlorides and tertiary chlorides, specifically, promote the reaction.

These observations from the mechanism for the “unzipping” of poly(vinyl chloride) is to be explained.

Concept introduction:

The “unzipping” of PVC follows E1 mechanism in acidic medium. So, the stability of the carbocation is a matter in this case. As the stability of the carbocation increases, the rate of E1 reaction increases. The process of cutting (scission) of the polymer to the corresponding monomer is known as unzipping. The stability order of carbocation is Primary < Secondary < Benzylic, allylic < Tertiary.

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