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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→HOC(CH3)2+CH3CH2CH2OC(CH3)2+KBrEliminationreactionCH3CH2CH2Br+KOC(CH3)2→CH3CH=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→CH3CH=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’s a single step reaction.

CH3CH2CH2Br+KOC(CH3)2→HOC(CH3)2+CH3CH2CH2OC(CH3)2+KBrEliminationreaction

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Most popular questions from this chapter

Ethers can often be prepared by SN2 reaction of alkoxide ions,RO- ,with alkyl halides. Suppose you wanted to prepare cyclohexyl methylether. Which of the two possible routes shown below would youchoose? Explain.

Question: Order each of the following sets of compounds with respect to reactivity:

b. (CH3)3 CCI (CH3)3 CBr (CH3)3 COH

Compound X is optically inactive and has the formulaC16H16Br2. On treatment with strong base, X gives hydrocarbon Y,C16H14. 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 formulaC7H6O. 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?

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

(b) An organohalide that will not undergo nucleophilic substitution

We saw in Section 8-7 that bromohydrins are converted into epoxides when treated with base. Propose a mechanism, using curved arrows to show the electron flow.
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