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Chapter 7: PROBLEM 7.8 (page 255)

Question: CPC (cetylpyridinium chloride), an antiseptic found in throat lozenges and mouthwash, is synthesized by the following reaction. Draw the structure of CPC.

Short Answer

Expert verified

The structure of CPC is shown below:

Step by step solution

01

CPC

CPC stands for cetylpyridinium chloride, which is an example of a cationic surfactant and has a quaternary ammonium portion. It finds application in toothpaste and sprays. It also functions as an antiseptic

02

Reaction of Lewis base and Lewis acid

The lone pair of nitrogen of pyridine (acts as Lewis base) donates its electron pair to the electrophilic carbon atom of 1-chlorohexadecane (acts as Lewis acid). This leads to the removal of the chlorine group.

The complete reaction is shown below:

Structure and formation of CP

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Most popular questions from this chapter

Question: An sp3 hybridized C-Cl bond is more polar than a sp2 hybridized C-Cl bond. (a) Explain why this phenomenon arises. (b) Rank the following compounds in order of increasing boiling point.

Question: Which of the following molecules contain a good leaving group?

a.

b.

c.

d.

Question: What happens to the rate of an SN1 reaction under each of the following conditions?

a. [RX] is tripled, and :Nu-stays the same.

b. Both [RX] and :Nu-are tripled.

c. [RX] is halved, and :Nu-stays the same.

d. [RX] is halved, and:Nu-is doubled.

Question: Fill in the appropriate reagent or starting material in each of the following reactions:

a.

b.

c.

d.

Question: Uridine monophosphate (UMP) is one of the four nucleotides that compose RNA, the nucleic acid that translates the genetic information of DNA into proteins needed by cells for proper function and development. A key step in the synthesis of UMP is the reaction of A with B to form C, which is then converted to UMP in one step. Draw a stepwise mechanism for this SN1 reaction.
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