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Chapter 11: Q4 P. (page 319)

What product would you expect from SN2reaction of 1-bromobutane with each of the following?

(a)NaI (b) KOH (c)H—C≡C—Li(d)NH3

Short Answer

Expert verified

(a)

(b)

(c)

(d)

Step by step solution

01

Nucleophilic bimolecular substitution SN2 reaction

The reaction is a nucleophilic substitution reaction where bond is broken and another is formed simultaneously. Two reacting species are involved in the rate determining step of the reaction. The term stands for substitution nucleophilic bimolecular.

SN2Reaction

02

Determine the product of the SN2 reaction of 1-bromobutane with each of the following

(a) NaI with 1-bromobutane


(b) KOH with 1-bromobutane

(c) H—C≡C—Liwith 1-bromobutane

(d) NH3with 1-bromobutane

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Most popular questions from this chapter

Question: Propose structures for compounds that fit the following descriptions:

(a) An alkyl halide that gives a mixture of three alkenes on E2 reaction

Question: There are eight diastereomers of 1,2,3,4,5,6-hexachlorocyclohexane. Draw each in its more stable chair conformation. One isomer loses HCl in an E2 reaction nearly 1000 times more slowly than the others. Which isomer reacts so slowly, and why?

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?

Reaction of iodoethane withyields a small amount of isonitrile,CH3CH2N≡C, along with the nitrileCH3CH2C≡Nas the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.

Propose a structure for an alkyl halide that gives only (E)-3-methyl-2-phenyl-2-pentene on E2elimination. Make sure you indicate the stereochemistry.
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