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Chapter 11: Q.11-50b (page 350)

Question:What products would you expect from the reaction of 1-bromopropane with each of the following?

(b) KOC(CH3)

Short Answer

Expert verified

Answer

CH3CH2CH2Br+KOC(CH3)2鈫扝OC(CH3)2+CH3CH2CH2OC(CH3)2+KBrEliminationreactionCH3CH2CH2Br+KOC(CH3)2鈫扖贬3CH=CH2+KBrSubstitutionreaction

Step by step solution

01

SN2 reaction

It is a nucleophilic substitution reaction in which old bond is broken and a new bond is formed. Both the processed occur simultaneously. Hence, it is a single step reaction.

Two reacting species are involved in the rate determining steps.

CH3CH2CH2Br+KOC(CH3)2鈫扖贬3CH=CH2+KBrSubstitutionreaction

02

E2 reaction

It is a nucleophilic elimination reaction in which old bond is broken and a new bond is formed. Both the processes occur simultaneously and no intermediate is formed.

Here, carbon hydrogen or halogen bond break to form new double bond. Hence, it鈥檚 a single step reaction.

CH3CH2CH2Br+KOC(CH3)2鈫扝OC(CH3)2+CH3CH2CH2OC(CH3)2+KBrEliminationreaction

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Most popular questions from this chapter

3-Bromo-1-butene and 1-bromo-2-butene undergoSN1 reaction at nearly the same rate, even though one is a secondary halide and the other is primary. Explain.

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.

Write the product you would expect from reaction of each of the following alkyl halides with (1)Na+-SCH3and (2)Na+-OH (green = Cl):

c)

Write the product you would expect from reaction of each of the following alkyl halides with (1)Na+-SCH3and (2)Na+-OH (green = Cl):

b)

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?
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