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Cyclic Hydrocarbons – Alicyclic Compounds
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Cyclic hydrocarbons; cyclopropane, cyclopentane, cyclohexane
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Organic ChemistryCyclic Hydrocarbons – Alicyclic Compounds
Many cases with sp3 + sp2 carbons, and a much smaller number with sp carbons (they want a bond angle
of 180o, which is hard to put in a ring)
Smallest one – Cyclopropane:
o Has angle strain because C-C-C angles are 60 o, but would prefer an angle of 109.5 o because
those carbons are supposed to be sp3 hybridized
o There is some torsional strain also
Substituted Cyclopropanes – if two substituents are present, isomers are possible
o B and c are cis/trans isomers of each other (or diastereomers)
o A is a constitutional isomer of b and/or c
Cyclobutane – some, but less angle strain
Actually Actual structure – slight butterfly
Cyclopentane – almost no angle strain, C-C-C bond angles = 104.5 o
, Cyclohexane – no angle strain at all, two limiting conformations with ‘perfect’ C-C-C bond angles
The chair is favored by 27 kJ/mol because:
There is actually a twist conformation which is 2nd best. Two different types of substituents:
The axial and equatorial sites exchange by a conformational change by chair-chair interconversion:
- If all substituents are H’s, A : B, 1 : 1
- But, if a non-H substituent is present
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