Chapter 9: Q43 E (page 286)
How would you carry out the following reactions to introduce deuterium into organic molecules?
(a)

b.

c.

d.

Short Answer
a.

b.

c.

d.

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Chapter 9: Q43 E (page 286)
How would you carry out the following reactions to introduce deuterium into organic molecules?
(a)

b.

c.

d.

a.

b.

c.

d.

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Show the terminal alkyne and alkyl halide from which the following products can be obtained. If two routes look feasible, list both.

Terminal alkynes react with and water to yield bromo ketones. For example:

Propose a mechanism for the reaction. To what reaction of alkenes is
the process analogous?
Question:Using any alkyne needed, how would you prepare the following alkenes?
(c) 3-Methyl-1-pentene
What products would you obtain by hydration of the following alkynes?

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.

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