Te C−C−C bond angles in furan are much smaller than those in benzene. The likely reason is which of the following:?

2019-03-03 3:12 pm
Te C−C−C bond angles in furan are much smaller than those in benzene. The likely reason is which of the following:

The hybridization of the carbon atoms in furan is different from that in benzene.
Furan does not have another resonance structure equivalent to the one above.
The atoms in a five-membered ring are forced to adopt smaller angles than in a six-membered ring.

回答 (2)

2019-03-03 4:43 pm
The answer is: The atoms in a five-membered ring are forced to adopt smaller angles than in a six-membered ring.

Refer to the diagrams below.

The first option is false. This is because the carbon atoms in benzene and those in furan are all in sp³ hybridization.

The second option is false. The statement is true, but this is not the reason to explain the difference in bond angles.

The third option is true. The carbon atoms in both benzene and furan are sp³ hybridized, and the angles between electron pairs are 120°. The interior angle of a hexagon (benzene ring) is 120°, while that of a pentagon (furan ring) is 108° which is smaller than 120°. In furan, the atoms are forces to adopt smaller angles.
2019-03-04 4:43 am
Furan does have two more resonance structures: -O+= with the double bonds to both of the two adjacent C atoms. Still no effect on bond angles.


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