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Chapter 9: Q68. (page 379)

Question: Draw a stepwise mechanism for the following reaction and explain the stereochemistry of the product.

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01

Step-by-Step SolutionStep 1: Epoxides

The organic compounds epoxides are examples of cyclic ethers and can be protonated with strong acids and can be converted into the compounds that contain -OH group.

02

Explanation

The given compound contains both an epoxide group and a -OH group. The epoxide reacts with the proton of the strong acid and then breaks its bond with the carbon atom and forms a carbocation intermediate.

The -OH group acts as a nucleophile, and it attacks on the carbocation intermediate from the backside. This is an example of an intramolecular SN2reaction. Thus, inversion in stereochemistry can be observed.

Mechanism

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Most popular questions from this chapter

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

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

Question: Draw two steps to convert (CH3)3CHOH into each of the following compounds: (CH3)2N3 , and (CH3)2CHOCH2CH3.

Question: An allylic alcohol contains an OH group on a carbon atom adjacent to a double bond. The treatment of allylic alcohol A with HCl forms a mixture of two allylic chlorides, B and C. Draw a stepwise mechanism that illustrates how both products are formed.

Question: Draw a stepwise mechanism for the following reaction.

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