Arrange the following alkenes in decreasing order of stability. [figure] Choose the correct answer from the options given below:
- III > I > II > IV
- III > II > I > IV
- I > III > II > IV
- I > III > IV > II
Answer
(3) I > III > II > IV
Solution
Stability of alkenes increases with the number of α-hydrogens (hyperconjugation) / alkyl groups on the C=C carbons:
I: 2,3-dimethylbut-2-ene, tetrasubstituted, 12 α-H
III: 2-methylbut-2-ene, trisubstituted, 9 α-H
II: trans-but-2-ene, disubstituted, 6 α-H
IV: cis-but-2-ene, disubstituted, 6 α-H
I > III > (II, IV)
Between II and IV: in the cis isomer the two CH3 groups are on the same side and repel each other (steric strain), so the trans isomer is more stable (lower heat of hydrogenation).
I > III > II > IV
Answer: (3)