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Chapter 9: Q. 9-9-8 P-b (page 272)

Using any alkyne needed, how would you prepare the following alkenes?

(b) cis-3-Heptene

Short Answer

Expert verified

It鈥檚 the reagent used in the reaction to convert the alkyne to an alkene by hydrogenation when 1 equivalent When 2 equivalent is present alkyne converts to alkane.

Step by step solution

01

Lindlar’s catalyst

It鈥檚 the reagent used in the reaction to convert the alkyne to an alkene by hydrogenation when 1 equivalent When 2 equivalent is present alkyne converts to alkane.

02

Formation of cis-3-Heptene

Alkyne hydrogenation to alkene occurs when a less active Lindlar鈥檚 catalyst is used which is a finely divided palladium metal with lead acetate and quinoline, an aromatic amine. The hydrogenation occurs with syn stereochemistry.

03

Reaction with Lindlar’s catalyst

When alkyne reacts with Lindlar鈥檚 catalyst then it breaks the three out of one bond and converts alkyne to an alkene by the addition of hydrogen to the atom and forms alkene as shown:

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Most popular questions from this chapter

The pkaof acetone, CH3COCH3, is 19.3. Which of the following bases is strong enough to deprotonate acetone?

(c) NaHCO3(pkaof H2CO36.4)

Question: How would you carry out the following conversions? More than one

step may be needed in some instances.

Occasionally, a chemist might need to invert the stereochemistry of an alkene鈥攖hat is, to convert a cis alkene to a trans alkene, or vice versa. There is no one-step method for doing an alkene inversion, but the transformation can be carried out by combining several reactions in the proper sequence. How would you carry out the following reactions?

(a)tran-5-decene鈫�?cis-5-decene

(b)cis-5-decene鈫�?trans-5-decene

Give IUPAC names for the following compounds:

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.
See all solutions

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