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Chapter 9: Q80. (page 382)

Question: Draw a stepwise mechanism for the following reaction.

Short Answer

Expert verified

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: Draw the organic product(s) formed when is treated with each reagent.

a. H2SO4

b. NaH

c. HCl +ZnCl2

d. HBr

e.SOCl2, pyridine

f. PBr3

g. TsCl, pyridine

h. [1] NaH; [2]

i. [1]TsCl, pyridine;[2] NaSH

j. POCl3, pyridine

Question: Draw the products of each reaction and indicate the stereochemistry where appropriate.

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b.

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f.

g.

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i.

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Question: If the reaction of an alcohol with PBr3follows anSN2 mechanism, what is the stereochemistry of the alkyl bromide formed from (R)-butan-2-ol?

Question: Treatment of cis-4-bromocyclohexanol with HO鈥� affords compound A and cyclohex-3-en-1-ol. Treatment of trans-4-bromocyclohexanol under the same conditions forms compound B and cyclohex-3-en-1-ol. A and B contain different functional groups and are not isomers of each other. Propose structures for A and B and offer an explanation for their formation
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