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Chapter 9: Q31P (page 494)

Question:The application box in the margin of page 473 states, “The 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.” 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

Develop syntheses for the following compounds, using acetylene and compounds containing no more than four carbon atoms as your organic starting materials.

(a) 3-methylnon-4-yn-3-ol (“3-ol” means there is an OH group on C3.)

(b) cis-1-ethyl-2-methylcyclopropane

(c)

(d) meso-hexane-3,4-diol

Deduce the structure of each compound from the information given. All unknown in this problem have molecular formula C8H12.

(a)Upon catalytic hydrogenation, unknown Wgives cyclooctane. Ozonolysis of W,followed by reduction with dimethylsulfide, gives octanedioic acid,HOOC-(CH2) 6-COOH . Draw the structure of W.

(b)Upon catalytic hydrogenation, unknown Xgives cyclooctane. Ozonolysis of X,followed by reduction with dimethyl sulfide, gives two equivalents of butanedial , O =CH -CH2 CH 2-CH = O. Draw the structure of X.

(c) Upon catalytic hydrogenation, unknown Y gives cyclooctane. Ozonolysis of Y, followed by reduction with dimethyl sulfide, gives a three-carbon dialdehyde and a five-carbon dialdehyde. Draw the structure of Y.

(d) Upon catalytic hydrogenation, unknown Z gives cis-bicyclo[4.2.0]octane. Ozonolysis of Z, followed by reduction with dimethyl sulfide, gives a cyclobutane with a three-carbon aldehyde (-CH2-CH2-CHO ) group on C1 and a one-carbon aldehyde (CHO) group on C2. Draw the structure of Z.

Propose a mechanism for the entire reaction of pent-1-yne with 2 moles of HBr. Show why Markovnikov’s rule should be observed in both the first and second additions of HBr.

Question:Using cyclooctyne as your starting material, show how you would synthesize the following compounds. (Once you have shown how to synthesize a compound, you may use it as the starting material in any later parts of this problem.)

(a)cis-cyclooctene

(b)cyclooctane

(c)trans-1,2-dibromocyclooctane

(d)cyclooctanone

(e)1,1-dibromocyclooctane

(f)3-bromocyclooctene

(g)cyclooctane-1,2-dione

(h)

(i)

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?
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