a) Interpretation: The product expected when 5-methylcycloheptene reacts with NBS is to be shown. If more than one product is possible the structures of all of them are to be shown. Concept introduction: NBS is used mainly for allylic bromination. An unsymmetrical alkene will lead to a mixture of products as two different allyl radicals will be produced as a result of delocalization. The two products are not formed in equal amounts because the intermediate allylic radical is not symmetrical and the reaction at two ends will not take place to the same extent. Reaction at less hindered primary side is more favored. To show: The structures of all the products expected when 5-methylcycloheptene reacts with NBS.

Question

Consider the following two acid-base reactions: OH OHI Based on what you know about the compounds and their acidity, which direction would you expect both of these reactions to proceed? Show your reasoning. A pKa table has been provided in case you need it. Functional group Example pka CHA -50 Alkane -35 Amine : NH3 Alkyne RH 25 Water HO-H 169 16 10 Protonated amines NH 10 5 Carboxylic acids OH Hydrochloric acid HCI A chemist intends to run the following reaction on the three substrates shown below: H₂O R-CI product room temp. Cl Cl (1) (2) (3) They find one will react quickly, one slowly, and one will not react at all. Which is which, and why? HINT: What is the reaction they're trying to do? Does that mechanism tell you anything about why something would be favored?

Answer 1

Question

Chapter 10.4, Problem 7P

Interpretation Introduction

a)

Interpretation:

The product expected when 5-methylcycloheptene reacts with NBS is to be shown. If more than one product is possible the structures of all of them are to be shown.

Concept introduction:

NBS is used mainly for allylic bromination. An unsymmetrical alkene will lead to a mixture of products as two different allyl radicals will be produced as a result of delocalization. The two products are not formed in equal amounts because the intermediate allylic radical is not symmetrical and the reaction at two ends will not take place to the same extent. Reaction at less hindered primary side is more favored.

To show:

The structures of all the products expected when 5-methylcycloheptene reacts with NBS.

Interpretation Introduction

b)

Interpretation:

The product expected when 2-methyl-3-hexene reacts with NBS is to be shown. If more than one product is possible the structures of all of them are to be shown.

Concept introduction:

NBS is used mainly for allylic bromination. An unsymmetrical alkene will lead to a mixture of products as two different allyl radicals will be produced as a result of delocalization. The two products are not formed in equal amounts because the intermediate allylic radical is not symmetrical and the reaction at two ends will not take place to the same extent. Reaction at less hindered primary side is more favored.

To show:

The structures of all the products expected when 2-methyl-3-hexene reacts with NBS.

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