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Chapter 9: q. 9-9-8 P-a (page 272)

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

(a) trans-2-Octene

Short Answer

Expert verified

Alkyne to an alkene uses sodium or lithium metal as the reducing agent in liquid ammonia. This method is complementary to Lindlar’s reduction because it produces trans rather than cis alkenes. Hence we want the trans product so use Li metal.

Step by step solution

01

Formation of trans-2-Octene

Alkyne to an alkene uses sodium or lithium metal as the reducing agent in liquid ammonia. This method is complementary to Lindlar’s reduction because it produces trans rather than cis alkenes. Hence we want the trans product so use Li metal.

02

Reaction with liquid ammonia

When alkyne reacts with ammonia in the presence of lithium then it breaks the three out of one bond and converts alkyne to an alkene by the addition of hydrogen to the atom but the addition must be in trans relation because of the presence of lithium-ion.

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Most popular questions from this chapter

How would you prepare the following carbonyl compounds starting from an alkyne (reddish-brown Br)?

b.

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

step is needed in each case.

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

a.CH3CH2CH2C≡CH

A cumulene is a compound with three adjacent double bonds. Draw an orbital picture of a cumulene. What kind of hybridization do the two central carbon atoms have? What is the geometric relationship of the substituents on one end to the substituents on the other end? What kind of isomerism is possible? Make a model to help see the answer.

R2C=C=C=CR2

A cumulene

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.
See all solutions

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