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Chapter 15: Q15-15-32E (page 477)

Cycloheptatrienone is stable, but cyclopentadienone is so reactive that it can鈥檛 be isolated. Explain, taking the polarity of the carbonyl group into account.

Cycloheptatrienone Cyclopentadienone

Short Answer

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Cycloheptatrienone

Cyclopentadienone

Step by step solution

01

Carbonyl group

When a carbonyl group is polarized it places a positive charge on the ring carbon which makes cycloheptatrienone aromatic and cyclopentadienone anti aromatic based on the huckle鈥檚 rule of aromaticity.

02

Aromatic and antiaromatic

The cycloheptatrienone ring in B contains six pi electrons and is aromatic according to Huckel鈥檚 rule whereas the cyclopentadienone ring in D contains four pi electrons and is antiaromatic. The resonance forms of cycloheptatrienone and cyclopentadienone are represented as:

Cycloheptatrienone

Cyclopentadienone

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