Chapter 9: Q39 E (page 286)
How would you carry out the following transformation? More than one
step is needed.
Chapter 9: Q39 E (page 286)
How would you carry out the following transformation? More than one
step is needed.
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Get started for freeDraw structures corresponding to the following names:
(a)3,3-Dimethyl-4-octyne
(b)3-Ethyl-5-methyl-1,6,8-decatriyne
(c)2,2,5,5-Tetramethyl-3-hexyne
(d)3,4-Dimethylcyclodecyne
(e)3,5-Heptadien-1-yne
(f)3-Chloro-4,4-dimethyl-1-nonen-6-yne
(g)3-sec-Butyl-1-heptyne
(h)5-tert-Butyl-2-methyl-3-octyne
The final step in the hydration of an alkyne under acidic conditions is the tautomerization of an enol intermediate to give the corresponding ketone. The mechanism involves a protonation followed by a deprotonation.
Show the mechanism for each of the following tautomerizations.
Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.
The pkaof acetone, CH3COCH3, is 19.3. Which of the following bases is strong enough to deprotonate acetone?
(b)
A hydrocarbon of unknown structure has the formula C8H10. On catalytic hydrogenation over the Lindlar catalyst, 1 equivalent of H2 is absorbed. On hydrogenation over a palladium catalyst, 3 equivalents of H2 are absorbed.
(a) How many degrees of unsaturation are present in the unknown structure?
(b) How many triple bonds are present?
(c) How many double bonds are present?
(d) How many rings are present?
(e) Draw a structure that fits the data.
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