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Chapter 21: 86P (page 817)

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.

Short Answer

Expert verified

The nucleophilic attack occurs on the electrophilic position. The carbon bonded to the Cl, Br, I is more electrophilic, therefore, the nucleophile attacks on the carbon.

The carbonyl carbon also undergoes the nucleophilic attack and forms the respective product.

Step by step solution

01

Nucleophilic attack

The nucleophilic attack occurs on the electrophilic position. The carbon bonded to the Cl, Br, I is more electrophilic, therefore, the nucleophile attacks on the carbon.

The carbonyl carbon also undergoes the nucleophilic attack and forms the respective product.

02

Explanation

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

First Step

Stepwise Mechanism

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Most popular questions from this chapter

Devise a synthesis of each compound from the given starting materials. You may also use organic alcohols having four or fewer carbons, and any organic or inorganic reagents

a)

b)

c)

Maltose is a carbohydrate present in malt, the liquid obtained from barley and other grains. Although maltose has numerous functional groups, its reactions are explained by the same principles we have already encountered.

a. Label the acetal and hemiacetal carbons.b. What products are formed when maltose is treated with each of the following reagents: [1] ; [2] and HCl; [3] excess NaH, then excess ?c. Draw the products formed when the compound formed in Reaction [3] of part (b) is treated with aqueous acid.The reactions in parts (b) and (c) are used to determine structural features of carbohydrates like maltose. We will learn much more about maltose and similar carbohydrates in Chapter 28.

Consider the para-substituted aromatic ketones, NO2C6H4COCH2 (p-nitroacetophenone) and CH3OC6H4COCH3 (p-methoxyacetophenone).

a. Which carbonyl compound is more stable?

b. Which compound forms the higher percentage of hydrate at equilibrium?

c. Which compound exhibits a carbonyl absorption at a higher wavenumber in its IR spectrum?

Explain your reasoning in each part.

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

a.

b.

c.

Draw the products of each reaction.

a.

b.
See all solutions

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