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Chapter 9: Q63. (page 379)

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

Short Answer

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Answer

Step by step solution

01

Step-by-Step SolutionStep 1: Reaction of ether with strong acid

The strong acids will protonate the oxygen atom of ether. Then a most stable carbocation intermediate is formed during this process.

02

Ether with tertiary butyl group

When an ether molecule consists of a tertiary butyl group in it, then the reaction of ether with strong acid leads to an elimination reaction from the tertiary butyl radical.

03

Explanation

The given acid CF3CO2His a strong acid, and it protonates the given ether and forms a tertiary butyl carbocation intermediate. This tertiary butyl carbocation further undergoes an elimination reaction and forms the products.

The mechanism of the reaction is as shown:

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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 the product of the following reaction, one step in the synthesis of the antiplatelet agent clopidogrel used to reduce the risk of stokes.

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

Question: Draw the products formed when ethylene oxide is treated with each reagent.

a.HBrb.H2O(H2SO4)c.[1]CH3CH2O;[2]H2Od.[1]CH3C鈮�N;[2]H2Oe.[1]O-H;[2]H2Of.[1]CH3S;[2]H2O

Question: Name each thiol.

a.

b.
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