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Chapter 8: Q.61 (page 330)

Draw a stepwise, detailed mechanism for the following reaction.

Short Answer

Expert verified

The mechanism for the formation of the substitution and elimination products are shown below:

Step by step solution

01

Types of reactions

Weak bases and weak nucleophiles such as water promote a mixture of both SN1 and E1 reactions.Here water is used, which acts both as a weak base and weak nucleophile. As a result, they give a mixture of both SN1 and E1 reactions.

02

Types of reactions by tertiary halides

Tertiary halides undergo a SN1 and E1 reaction respectively when a weak nucleophile and a weak base are used, such as water which is so observed in this reaction.

03

Similarities in both the reaction pathway

Both SN1 and E1 reactions are two-step processes, and carbocation formation is the rate-determining step.

By considering all the steps, the mechanism for the formation of the substitution and elimination products are shown below:

Representation of the detailed reaction schemes

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Most popular questions from this chapter

Draw the major product formed when (R)-1-chloro-3-methylpentane is treated with each reagent: (a)NaOCH2CH3 ; (b) KCN; (c) DBU.

Although dehydrohalogenation occurs with anti periplanar geometry, some eliminations have syn periplanar geometry. Examine the starting material and product of each elimination, and state whether the elimination occurs with syn or anti periplanar geometry.

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Elimination of HBr from 2-bromobutane affords a mixture of but-1-ene and but-2-ene. With sodium ethoxide as base, but-2-ene constitutes 81% of the alkene products, but with potassium tert-butoxide, but-2-ene constitutes only 67% of the alkene products. Offer an explanation for this difference.

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