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Chapter 9: Q57. (page 378)

Question: Draw a stepwise, detailed mechanism for the following reaction.

Short Answer

Expert verified

Answer

The mechanism of the reaction is as shown below.

Step by step solution

01

Step-by-Step SolutionStep 1: Stability of carbocation

During the (unimolecular) reaction, the most stable carbocation intermediate will be formed if the rearrangement of alkyl shift or hydride shift does not lead to the formation of the most stable carbocation

02

The mechanism of the given reaction

This reaction takes place in the presence of a sulfuric acid catalyst.

The secondary carbocation becomes the most stable 3掳carbocationdue to the alkyl shift. Then, will be eliminated, and it leads to the formation of the respective alkene

Mechanism of the reaction

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Most popular questions from this chapter

Question: What alkenes are formed when each alcohol is dehydrated with TsOH? Label the major product when a mixture results.

a.

b.

c.

d.

Question: Which mechanism is favored by the use of crown ethers in nonpolar solvents, SN1orSN2 ?

Question: Epoxides are converted to allylic alcohols with non-nucleophilic bases such as lithiumdiethylamide [LiNCH2CH32] . Draw a stepwise mechanism for the conversion of1,2-epoxycyclohexane to cyclohex-2-en-1-ol with this base. Explain why a strong bulky basemust be used in this reaction.

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掳or3掳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.

Question: Why is the boiling point of propane-1,3-diol higher than the boiling point of propane-1,2-diol [HOCH2CHOHCH3]role="math" localid="1648635549686" (215掳Cvs185掳C)? Why do both diols have a higher boiling point than butan-1-ol CH3CH2CH2CH2OH,118掳C ?
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