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Chapter 25: PROBLEM 25.21 (page 1019)

Question: Rank the following compounds in order of increasing basicity

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01

Basicity of arylamines and alkylamines

Arylamines (aniline) having a ring accept electrons pairs from the amine group. Therefore, aniline is less basic than alkylamines.

Alkylamines have an alkyl group that donates electrons and increases their basicity.

02

Amide

Amide also contains nitrogen which is bonded with the carbonyl group. The lone pair of electrons in the amide delocalize to the carbonyl group. Therefore, amide is less basic than aniline.

03

Explanation

The increasing order of basicity is as shown.

Increasing basicity order

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Most popular questions from this chapter

Devise a synthesis of each biologically active compound from benzene.

Rank the following compounds in order of increasing basicity and explain the order you chose.

Question: Which N atom in each compound is more basic? What product is formed when each compound is treated with HCl?

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Question: Varenicline (trade name Chantix) is a drug used to help smokers quit their habit.

(a) Which N atom in varenicline is most basic? Explain your choice.

(b) What product is formed when varenicline is treated with HCl?

Question: Devise a synthesis of each compound from benzene. You may use any other organic or inorganic reagents.

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