Which one of the following alkenes will react faster with H2 under catalytic hydrogenation conditions ?
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Answer
(1) [figure]
Solution
In catalytic hydrogenation, the alkene is adsorbed on the metal surface and both H atoms are added from the same side (syn addition).
∵ Bulky R groups on the double bond hinder its approach to the catalyst surface, the rate decreases as substitution increases; a more substituted alkene is also more stable (lower heat of hydrogenation).
⇒ Rate of hydrogenation: less substituted > more substituted, i.e. disubstituted > trisubstituted > tetrasubstituted
Among the two disubstituted alkenes, in the cis-1,2-disubstituted alkene (option 1) each doubly bonded carbon carries only one R group, so neither carbon is crowded (in option 2 one carbon carries both R groups); it is also the less stable of the two and reacts faster.
∴ The alkene in option (1) reacts fastest.
Answer: (1)