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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

Give the IUPAC name for each aldehyde.

a.

b.

c

The boiling point of butan-2-one ( 79.64oC ) is significantly higher than the boiling point of diethyl ether ( 34.6OC), even though both compounds exhibit dipole–dipole interactions and have comparable molecular weights. Offer an explanation.

What Wittig reagent and carbonyl compound are needed to prepare each alkene? When two routes are possible, indicate which route, if any, is preferred.

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b.

c.

Draw the products of each reaction.

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b.

How would you use a protecting group to carry out the following transformation?
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