Whether the given reaction occurs by an S N 2 , S N 1 , E2 , or E1 mechanism is to be determined and a complete, detailed mechanism that accounts for the formation of the two products is to be drawn. Concept introduction: S N 2 and S N 1 are nucleophilic substitution mechanisms. The first is a single-step bimolecular reaction while the second is a two-step unimolecular reaction. An E1 reaction is a two-step, unimolecular elimination reaction. The reaction involves the formation of a carbocation intermediate in the first, rate-determining step. The carbocation may be subject to a rearrangement if it leads to a more stable carbocation. In the second step, a base abstracts a proton from an adjacent carbon to form the product. Because of the possibility of carbocation rearrangement, the reaction often yields a mixture of constitutional isomers. An E2 elimination reaction involves both the substrate and the base in a single concerted step. In most cases, this results in a single product.

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1/2 - 51% + » GAY Organic Reactions Assignment /26 Write the type of reaction that is occurring on the line provided then complete the reaction. Only include the major products and any byproducts (e.g. H₂O) but no minor products. Please use either full structural diagrams or the combination method shown in the lesson. Skeletal/line diagrams will not be accepted. H3C 1. 2. CH3 A Acid OH Type of Reaction: NH Type of Reaction: + H₂O Catalyst + HBr 3. Type of Reaction: H3C 4. Type Reaction: 5. H3C CH2 + H2O OH + [0] CH3 Type of Reaction: 6. OH CH3 HO CH3 + Type of Reaction: 7. Type of Reaction: + [H]

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Question

Chapter 9, Problem 9.42P

Interpretation Introduction

Interpretation:

Whether the given reaction occurs by an $SN2$ , $SN1$ , $E2$ , or $E1$ mechanism is to be determined and a complete, detailed mechanism that accounts for the formation of the two products is to be drawn.

Concept introduction:

$SN2$ and $SN1$ are nucleophilic substitution mechanisms. The first is a single-step bimolecular reaction while the second is a two-step unimolecular reaction.

An $E1$ reaction is a two-step, unimolecular elimination reaction. The reaction involves the formation of a carbocation intermediate in the first, rate-determining step. The carbocation may be subject to a rearrangement if it leads to a more stable carbocation. In the second step, a base abstracts a proton from an adjacent carbon to form the product. Because of the possibility of carbocation rearrangement, the reaction often yields a mixture of constitutional isomers.

An E2 elimination reaction involves both the substrate and the base in a single concerted step. In most cases, this results in a single product.

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1/2 - 51% + » GAY Organic Reactions Assignment /26 Write the type of reaction that is occurring on the line provided then complete the reaction. Only include the major products and any byproducts (e.g. H₂O) but no minor products. Please use either full structural diagrams or the combination method shown in the lesson. Skeletal/line diagrams will not be accepted. H3C 1. 2. CH3 A Acid OH Type of Reaction: NH Type of Reaction: + H₂O Catalyst + HBr 3. Type of Reaction: H3C 4. Type Reaction: 5. H3C CH2 + H2O OH + [0] CH3 Type of Reaction: 6. OH CH3 HO CH3 + Type of Reaction: 7. Type of Reaction: + [H]

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