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Chapter 12: PROBLEM 12.46 (page 489)

Question: a) What product is formed in Step [1] of the following reaction sequence?

(b) Draw a mechanism for Step [2] that accounts for the observed stereochemistry.

(c) What reaction conditions are necessary to form chiral A from prop-2-en-1-ol

Short Answer

Expert verified

Answer

a.

b.

c.

Step by step solution

01

Reaction of alcohols with methane sulfonyl chloride

The reaction of alcohols with methane sulfonyl chloride yields the corresponding methane sulfonates by the replacement of the hydrogen atom of the OH group by SO2CH3 .

02

Product obtained in step [1]

The reaction of the given compound with CH3SO2Cl is shown below:

Reaction of A with CH3SO2Cl

03

Mechanism of step [2]

The mechanism of the given reaction is provided below.

Mechanism

04

Preparation of chiral A using prop-2-en-1-ol

The preparation of chiral A from prop-2-en-1-ol can be carried out as shown below.

Synthesis of A

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Most popular questions from this chapter

Question: It is sometimes necessary to isomerize a cis alkene to a trans alkene in a synthesis, a process that cannot be accomplished in a single step. Using the reactions that you have learned in Chapters 8–12, devise a stepwise method to convert cis-but-2-ene to trans-but-2-ene.

Question: DHA is a fatty acid derived from fish oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid [CH3CH22OCO2H]and ozonolysis forms CH3CH2CHO,CH2(CHO)2(five equivalents), and HCOCH2CH2CO2H. What is the structure of DHA if all double bonds have the Zconfiguration?

Question: Identify A in the following reaction sequence and draw a mechanism for the conversion of A to B. B has been converted to (S,S)-reboxetine, an antidepressant marketed outside the United States.

Question: Label each reaction as oxidation, reduction, or neither.

a.

b.

c.

d.

Question: An unknown compound A of molecular formula C10H18O reacts with H2SO4 to form two compounds (B and C) of molecular formula C10H16. B and C both react with H2 in the presence of Pd-C to form decalin. Ozonolysis of B forms D, and ozonolysis of C forms a diketone E of molecular formula C10H16O2. Identify the structures of compounds A, B, C and E.
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