The structure of a conjugated diene that gives the same product from both 1,2 and 1,4 addition of HBr is to be given. Concept introduction: Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted conjugated 1,3-dienes a single product is produced in both types of addition. To give: The structure of a conjugated diene that gives the same product from both 1,2 and 1,4 addition of HBr.

Question

1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.

Answer 1

Question

Chapter 14.SE, Problem 29AP

Interpretation Introduction

Interpretation:

The structure of a conjugated diene that gives the same product from both 1,2 and 1,4 addition of HBr is to be given.

Concept introduction:

Conjugated dienes when treated with one mole of HCl in ether undergo both 1,2 and 1,4 addition of HCl to yield different products. With unsubstituted conjugated 1,3-dienes a single product is produced in both types of addition.

To give:

The structure of a conjugated diene that gives the same product from both 1,2 and 1,4 addition of HBr.

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1. Answer the questions about the following reaction: (a) Draw in the arrows that can be used make this reaction occur and draw in the product of substitution in this reaction. Be sure to include any relevant stereochemistry in the product structure. + SK F Br + (b) In which solvent would this reaction proceed the fastest (Circle one) Methanol Acetone (c) Imagine that you are working for a chemical company and it was your job to perform a similar reaction to the one above, with the exception of the S atom in this reaction being replaced by an O atom. During the reaction, you observe the formation of three separate molecules instead of the single molecule obtained above. What is the likeliest other products that are formed? Draw them in the box provided.

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