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Chapter 9: Q12. (page 346)

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

Short Answer

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Answer

The alcohols in order of increasing reactivity, when dehydrated with H2So4are mentioned below.

Step by step solution

01

Step-by-Step Solution Step 1: Dehydration of an alcohol

The elimination of water molecules from alcohol in the presence of acid is termed the dehydration of alcohol.

02

Order of ease of dehydration of alcohol and stability of carbocation

The decreasing order of the ease of the dehydration of alcohol in the presence of acid is given as follows.

3掳alcohol>2掳alcohol>1掳alcohol

The above order is dependent on the stability of the carbocation. The order is given as follows.

3掳alcohol>2掳alcohol>1掳alcohol

03

Order of increasing reactivity

The formation of a carbocation in the given compounds is as follows.

Order of carbocation

Thus, the increasing order of dehydration is shown below.

Order of dehydration

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Most popular questions from this chapter

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: Draw a stepwise mechanism for each reaction

a.

b.

Question: Draw two different routes to each of the following ethers using a Williamson ether synthesis. Indicate the preferred route (if there is one).

a.

b.

c.

Question: If the reaction of an alcohol with SOCl2and pyridine follows an SN2 mechanism, what is the stereochemistry of the alkyl chloride formed from (R)-butan-2-ol?

Question: Although alcohol V gives a single alkene W when treated with POCl3 and pyridine, three isomeric alkenes (X鈥揨) are formed on dehydration with H2SO4. Draw a stepwise mechanism for each reaction and explain why the difference occurs.
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