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Ring opening reactions relieves the strain leads to more stable open
chain compounds. More strained means more unstable and more prone to
undergo ring opening reactions.
4 BITSPilani, Pilani Campus
Cyclopentane
• If planar, angles would be 108o but all hydrogens would
be eclipsed.
Newman
projection
Chair conformation
X
X Eaxial – Eequatorial X Eaxial – Eequatorial
-H 0.0 -COOH 2.9
-CN 0.4 -CH3 3.8
-F 0.5 -CH2CH3 4.0
-Cl 1.0 -CH(CH3)2 4.6
-Br 1.0 Ph 6.3
-OH 2.1 -C(CH3)3 11.4
12 BITSPilani, Pilani Campus
1-methylcyclohexane
trans-1,2-Dimethylcyclohexane
trans-1,4-Dimethylcyclohexane cis-1,4-Dimethylcyclohexane
Stable conformation