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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.

Short Answer

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Answer

Step by step solution

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 product formed when is treated with each reagent.

a.SOCl2, Pyridine

b. TsCl, Pyridine

c. H2SO4

d. HBr

e. PBr3then NaCN

f. POCl3,Pyridine

Question: The cis and trans isomers of 2,3-dimethyloxirane both react with 鈥揙H to give butane-2,3-diol. One stereoisomer gives a single achiral product, and one gives two chiral enantiomers. Which epoxide gives one product and which gives two?

Question: Draw the products of each reaction, indicating the stereochemistry around any stereogenic centers.

a.

b.

c.

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

Question: Answer each question using the ball-and-stick model of compound A.

a. Give the IUPAC name for A, including R,Sdesignations for stereogenic centers.

b. Classify A as a 1掳,2掳,3掳alcohol.

c. Draw a stereoisomer for A and give its IUPAC name.

d. Draw a constitutional isomer that contains an OH group and give its IUPAC name.

e. Draw a constitutional isomer that contains an ether and give its IUPAC name.

f. Draw the products formed (including stereochemistry) when A is

treated with each reagent: [1] NaH; [2] ; [3] , pyridine;

[4] HCl; [5] ,pyridine; [6] TsCl, pyridine.
See all solutions

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