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Chapter 9: Q80. (page 382)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

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Answer

The stepwise mechanism of the given reaction is shown hereunder.

Mechanism

Step by step solution

01

Step-by-Step solutionStep 1: Proton transfer reaction 

The base transfers its electron density to the acidic hydrogen and abstracts it from the acidic compound.

02

Ring-opening reaction

Upon undergoing the proton transfer reaction, the nucleophilic site thus formed on the then acid attacks the carbon attached to the electronegative atom. During this step, the ring opens.

03

Mechanism of the given reaction

NaOH attacks on the acidic hydrogen, i.e., the one attached to the oxygen atom. The newly formed carbanion species then attacks the carbon attached to the highly electronegative atom.

Thus, the ring breaks and an epoxide is formed. The mechanism of the given reaction is shown hereunder

Mechanism

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Most popular questions from this chapter

Question: What other alkene is also formed along with Y in Sample Problem 9.3? What alkenes would form from X if no carbocation rearrangement occurred?

Question: Rank the alcohols in order of increasing reactivity when dehydrated with H2So4

Question: Sometimes carbocation rearrangements can change the size of a ring. Draw a stepwise, detailed mechanism for the following reaction.

Question: Draw the products of each reaction, and include the stereochemistry at any stereogenic center in the products.

a.

b.

c.

Question:Rearrangements can occur during the dehydration of alcohols even though no carbocation is formed-that is, a 1,2-shift occurs as the C-O+H2 bond is broken, forming a more stable 2°or3°carbocation, as shown. Using this information, draw a stepwise mechanism that shows how CH3CH2CH2CH2OH is dehydrated with H2SO4to form a mixture of CH3CH2CH=CH2and the cis and trans isomers of CH3CH=CHCH3. We will see another example of this type of rearrangement in Section 18.5C.
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