Chapter 9: Q40P (page 495)
Show how you would convert the following starting materials into the target compound. You may use any additional reagents you need.
Chapter 9: Q40P (page 495)
Show how you would convert the following starting materials into the target compound. You may use any additional reagents you need.
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Get started for freeWhen 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: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
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)
Show how you would convert
(a) oct-3-yne to cis-oct-3-ene.
(b) pent-2-yne to trans-pent-2-ene.
(c) cis-cyclodecene to trans-cyclodecene.
(d) but-1-yne to cis-hex-3-ene.
Propose a mechanism for the reaction of pent-1-yne with HBr in the presence of peroxides. Show why anti-Markovnikov orientation results.
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