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Chapter 12: PROBLEM 12.4 (page 459)

Question: Which alkene in each pair has the larger Heat of hydrogenation?

a.

b.

Short Answer

Expert verified

Answer

a.


b.

Step by step solution

01

Heat of hydrogenation

When (C=C) is broken and new (C-H) are formed, some energy is released out, known as the heat of hydrogenation.

The stability of alkenes is inversely proportional to the heat of hydrogenation.

02

Stability of alkenes

One of the factors that affect the stability of alkenes is substituents. The number of substituents and their position defines the stability of alkenes.

03

Determination of alkenes with larger heat of hydrogenation

a. Cis alkenes are less stable than trans alkenes due to steric hindrance; therefore, cis alkenes will have larger heat of hydrogenation.

Cis and trans alkene

b. As the number of substitutions increases, the stability increases as hyperconjugation increases.

Di and Tri substituted alkene

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Most popular questions from this chapter

Question: One compound that contributes to the “seashore smell”at beaches in Hawai’s is dictyopterene D’ with excess H2in the presence of a Pd catalyst forms butylcycloheptane. Ozonolysis with O3 followed by (CH3)2S forms CH2(CHO)2,HCOCH2CH(CHO)2, and CH3CH2CHO. What are possible structures of dictyopterene D’?

Question: What alkane is formed when each alkene is treated with H2 and a Pd catalyst?

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b.

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Question: Oximene and myrcene, two hydrocarbons isolated from alfalfa that have the molecular formula C10H16, both yield 2,6-dimethyloctane when treated with H2and a Pd catalyst. Ozonolysis of oximene forms (CH3)2C=O, CH2=O, CH2(CHO)2and CH3COCHO. Ozonolysis of myrcene yields (CH3)2CO, CH2=O(two equiv), and HCOCH2CH2COCHO. Identify the structures of oximene and myrcene.

Question: What product is formed when CH3OCH2CH2C≡CCH2CHCH32 is treated with each reagent: (a) H2 (excess), Pd-C; ; (b) H2(1 equiv), Lindlar catalyst; (c) H2(excess), Lindlar catalyst; (d) Na,NH3 ?

Question: a) What product is formed in Step [1] of the following reaction sequence?

(b) Draw a mechanism for Step [2] that accounts for the observed stereochemistry.

(c) What reaction conditions are necessary to form chiral A from prop-2-en-1-ol

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