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Chapter 11: Q 11-11-20 P-a (page 347)

Tell whether each of the following reactions is likely to be S_N1, S_N2, E1, E1cB or E2:
a)

Short Answer

Expert verified

a) The given reaction is S_N2 reaction.

Step by step solution

01

SN2 reaction

A S_N2reaction is bimolecular and is a nucleophilic substitution reaction. In this reaction, bond breaking and forming take place simultaneously. A transition state is formed where a bond is made, and a broken bond is seen.

02

Whether the reaction is SN1, SN2, E1, E1cB or E2:

a) The given reaction occur by a mechanism because the substrate of the reaction is primary, and the nucleophile is nonbasic. The product formed is a substitution product.

The S_N2 mechanism

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Most popular questions from this chapter

Reaction of iodoethane withyields a small amount of isonitrile, ${CH}_{3} {CH}_{2} N \equiv C$ , along with the nitrile ${CH}_{3} {CH}_{2} C \equiv N$ as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.

Methyl esters ( ${RCO}_{2} {CH}_{3}$ ) undergo a cleavage reaction to yield carboxylate ions plus iodomethane on heating with LiI in dimethylformamide:

The following evidence has been obtained: (1) The reaction occurs much faster in DMF than in ethanol. (2) The corresponding ethyl ester ( ${RCO}_{2} {CH}_{2} {CH}_{3}$ ) cleaves approximately 10 times more slowly than the methyl ester. Propose a mechanism for the reaction. What other kinds of experimental evidence could you gather to support your hypothesis?

Question: Ignoring double-bond stereochemistry, what products would you expect from elimination reactions of the following alkyl halides? Which product will be the major product in each case?

Question: Arrange the carbocations below, in order of increasing stability.

c.

Compound X is optically inactive and has the formula $C_{16} H_{16} {Br}_{2}$ . On treatment with strong base, X gives hydrocarbon Y, $C_{16} H_{14}$ . Compound Y absorbs 2 equivalents of hydrogen when reduced over a palladium catalyst and reacts with ozone to give two fragments. One fragment, Z, is an aldehyde with formula $C_{7} H_{6} O$ . The other fragment is glyoxal, ${(CHO)}_{2}$ . Write the reactions involved, and suggest structures for X, Y, and Z. What is the stereochemistry of X?

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