Which of the following will produce the highest heat when 1.0 mole of each is hydrogenated in presence of Ni catalyst? I:CH2=CH2 II:CH3−CH=CH2 III:(CH3)2−C=CH−CH3 IV:CH3−C≡C−CH3 V:CH2=CH−CH=CH2
A
I
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B
II
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C
III
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D
IV
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E
V
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Solution
The correct option is DIII The stability of alkene can be determined by measuring the amount of energy associated with the hydrogenation of the molecule. Since the double bond is breaking in this reaction, the energy released in hydrogenation is proportional to the energy in the double bond of the molecule. Stability is simply a measure of energy. Lower energy molecules are more stable than higher energy molecules. More substituted alkenes are more stable than less substituted ones due to hyperconjugation. They have a lower heat of hydrogenation. The following illustrates the stability of alkenes with various substituents: V<I<II<IV<III