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Chapter 21: 85P (page 817)

Identify R and S in the following reaction sequence, and draw a mechanism for the conversion of R to S (molecular formula ). S was used in the synthesis of darunavir (trade name Prezista), used to treat HIV.

Short Answer

Expert verified

The ozonolysis occurs on the alkene. It forms aldehyde or ketone or both. The substituted carbon forms ketone and the unsubstituted carbon forms aldehyde in the presence of a reducing agent.

Step by step solution

01

Ozonolysis

The ozonolysis occurs on the alkene. It forms aldehyde or ketone or both. The substituted carbon forms ketone and the unsubstituted carbon forms aldehyde in the presence of a reducing agent.

02

Reducing agent

The sodium borohydride is the reducing agent which reduces aldehyde and ketone into the corresponding alcohol.The alcohol further undergoes intramolecular reaction forming the final product after abstraction of acidic hydrogen.

03

Explanation

The ozonolysis forms the aldehyde, which is further reduced from the sodium borohydride and forms the alcohol after workup.

The step-by-step reaction mechanism is as follows:

First Step

Second Step

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Most popular questions from this chapter

What carbonyl compound and amine are formed by the hydrolysis of each compound?

a.

b.

c.

Safrole is a naturally occurring acetal isolated from sassafras plants. Once used as a common food additive in root beer and other beverages, it is now banned because it is carcinogenic. What compounds are formed when safrole is hydrolysed with aqueous acid?

Draw a stepwise mechanism for the following reaction, a key step in the synthesis of conivaptan (trade name Vaprisol), a drug used in the treatment of low sodium levels.

Give the structure corresponding to each name.

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b. 3,3-dimethylcyclohexanecarbaldehyde

c. 3-benzoylcyclopentanone

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e. (R)-3-methylheptan-2-one

f. m-acetylbenzaldehyde

g. 2-sec-butylcyclopent-3-enone

h. 5,6-dimethylcyclohex-1-enecarbaldehyde

Draw the products of each reaction.

a.


b.

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d.

e.

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h.
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