Chapter 7: Problem 20
Show reagents and experimental conditions to bring about the following transformations.
Chapter 7: Problem 20
Show reagents and experimental conditions to bring about the following transformations.
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Get started for freePropose a synthesis of each compound starting from acetylene and any necessary organic and inorganic reagents. (a) 4 -Octyne (b) 4 -Octanone (c) cis-4-Octene (d) trans-4-Octene (e) 4-Octanol (f) meso- 4,5 -Octanediol
Hydration of 2-pentyne gives a mixture of two ketones, each with the molecular formula \(\mathrm{C}_{5} \mathrm{H}_{10} \mathrm{O}\). Propose structural formulas for these two ketones and for the enol from which each is derived.
Draw structural formulas for the major product(s) formed by reaction of 3 -hexyne with each of these reagents. (Where you predict no reaction, write NR.) (a) \(\mathrm{H}_{2}\) (excess)/ \(\mathrm{Pt}\) (b) \(\mathrm{H}_{2} /\) Lindlar catalyst (c) \(\mathrm{Na}\) in \(\mathrm{NH}_{3}(l)\) (d) \(\mathrm{BH}_{3}\) followed by \(\mathrm{H}_{2} \mathrm{O}_{2} / \mathrm{NaOH}\) (e) \(\mathrm{BH}_{3}\) followed by \(\mathrm{CH}_{3} \mathrm{COOH}\) (f) \(\mathrm{BH}_{3}\) followed by \(\mathrm{CH}_{3} \mathrm{COOD}\) (g) \(\mathrm{Cl}_{2}(1 \mathrm{~mol})\) (h) \(\mathrm{NaNH}_{2}\) in \(\mathrm{NH}_{3}(l)\) (i) \(\mathrm{HBr}(1 \mathrm{~mol})\) (j) \(\mathrm{HBr}(2 \mathrm{~mol})\) (k) \(\mathrm{H}_{2} \mathrm{O}\) in \(\mathrm{H}_{2} \mathrm{SO}_{4} / \mathrm{HgSO}_{4}\)
CC(C)(O)CC Oblivon Propose a synthesis for this
compound starting with a…
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Following is the structural formula of the tranquilizer meparfynol (Oblivon).
Using your reaction roadmap as a guide, show how to convert 3-hexyne into propanal. All of the carbon atoms of the target molecule must be derived from the starting material as efficiently as possible. Show all intermediate molecules synthesized along the way.
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