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Chapter 12: PROBLEM 12.47 (page 490)

Question: Draw the products formed after Steps and in the following three-step sequence. Then draw stepwise mechanisms for each step.

Short Answer

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Answer

Step by step solution

01

m-CPBA

m-CPBA is represented by the name meta-chloroperbenzoic acid, which is used for the formation of an epoxide at the double bond.

02

Conversion of epoxide into ether

When undergoing ring-opening, epoxides give alcohol that forms ether by attacking the C-X bond, where X is the halogen (Cl, Br, or I).

03

Explanation

The given substrate is an alkene with a halide bond. m-CPBA forms an epoxide at the alkene by giving oxygen to the alkene.

The base HO-attacks the epoxide from the less substituted site and forms diol.

In the third step, the base NaH abstracts the acidic hydrogen of OH, which leads to the attack of oxide on the C-Br bond.

The mechanism is shown as:

Ring opening of the epoxide

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Most popular questions from this chapter

Question: Hydrogenation of alkene A with D2 in the presence of Pd-C affords a single product B. Keeping this result in mind, what compound is formed when A is treated with each reagent:

(a) mCPBA; (b) Br2 , H2O followed by base? Explain these results.

Question: Sharpless epoxidation of allylic alcohol X forms compound Y. Treatment of Y with NaOH and C6H5SH in an alcohol鈥搘ater mixture forms Z. Identify the structure of Y and draw a mechanism for the conversion of Y to Z. Account for the stereochemistry of the stereogenic centers in Z. Z has been used as an intermediate in the synthesis of chiral carbohydrates.

Question: Draw the products formed when both cis- and trans-but-2-ene are treated with OsO4, followed by hydrolysis with NaHSO3+H2O. Explain how these reactions illustrate that syndihydroxylation is stereospecific.

Question: Devise a synthesis of each compound from CH3CH2OHas the only organic starting material; that is, every carbon in the product must come from a molecule of ethanol. You may use any other needed inorganic reagents.

Question: Draw the organic products formed when each alkene is treated with H2 / Pd-C. Indicate the three-dimensional structure of all stereoisomers formed.

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