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Chapter 9: Q31P (page 494)

Question:The application box in the margin of page 473 states, 鈥淭he addition of an acetylide ion to a carbonyl group is used in the synthesis of ethchlorvynol, a drug used to cause drowsiness and induce sleep.鈥� Show how you would accomplish this synthesis from acetylene and a carbonyl compound.

ethchlorvynol

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Synthesis of ethchlorovynol

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01

 Step-by-Step Solution Step 1: About ethchlorovynol

The sedative medication developed by the scientist Pfizer is ethchlorovynol. This drug is used for the treatment of insomnia. This drug is a member of carbinol that has a simpler structure.

02

About the structure of ethchlorovynol

The IUPAC name for ethchlorovynol is 1-chloro-3-ethylpent-1-en-4-yn-3-ol. This compound has one triple bond. The functional groups present in this compound are alcohol and chloro group.

03

Synthesis of ethchlorovynol

The (Z)-1-chloropent-1-en-3-one is treated with ethynide in the presence of sodium amide. On treatment with acid, ethchlorovynol is obtained. The mechanism is given below.

Synthesis of ethchlorovynol

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Most popular questions from this chapter

Predict the major product(s) of the following reactions:

(a) phenylacetylene + 2 HBr

(b) hex-1-yne + 2 HCl

(c) cyclooctyne + 2 HBr

(d) hex-2-yne + 2 HCl

Question: Show how you would synthesize each compound, beginning with acetylene and any necessary additional reagents.

(a) prop-2-yn-1-ol (propargyl alcohol)

(b) hept-2-yn-4-ol

(c) 2-phenylbut-3-yn-2-ol

(d) 3-methylhex-4-yn-3-ol

Question: Predict the products of the following acid-base reactions, or indicate if no significant reaction would take place.

(补)贬-颁鈮-贬+狈补狈贬2(b)H-C鈮�C-H+CH3Li(c)H-C鈮�C-H+NaOCH3(d)H-C鈮�C-H+NaOH(e)H-C鈮�CNa++NaOH(f)H-C鈮�CNa++H2O(g)H-C鈮�CNa++H2C=CH2(h)H2C=CH2+NaNH2(i)CH3OH+NaNH2

When compound Z is treated with ozone, followed by dimethyl sulfide and washing with water, the products are formic acid, 3-oxobutanoic acid, and hexanal.

Propose a structure for compound Z. What uncertainty is there in the structure you have proposed?

Question: Give IUPAC names for the following compounds.

a.

b.

c.

d.

e.

f.
See all solutions

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