Write the structural formulae of the two isomers with the molecular formula C_4H_8OC4H8O to illustrate functional group isomerism?

2 Answers
Jul 27, 2015

At first, just disregard the HH's. You use them later on to complete the valencies of the other atoms.

Explanation:

Since the net formula of a C_4C4 alkane is C_4H_10C4H10, apparently two HH's have been replaced by a double-bonded OO.

This can be done in only two different ways: at the end or somewhere in the middle.

Your isomers are (pictures from Wikipedia):
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CH_3-CH_2-CH_2-CHOCH3CH2CH2CHO
butanal or (butyric aldehyde)
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CH_3-CO-CH_2-CH_3CH3COCH2CH3
butanone (or methyl ethyl ketone)

The functional difference between aldehydes and ketones is that only the aldehyde can easily be oxidised to form a carbonic acid, in this case butanoic acid (or butyric acid). The ketones can only be destructively oxidised, by more powerful reactants.

Aug 17, 2015

An alternative way of assessing organic formulae is to invoke degrees of unsaturation. More isomers are possible.

Explanation:

As explained in the linky, C_4H_8OC4H8O has 1 degree of unsaturation. Each degree of unsaturation corresponds to a double bond (either C=CC=C, or C=OC=O), OROR a ring (a ring junction means 2 hydrogens are no longer needed for the chain termini. The alternative answer is indeed correct to identify the ketone and aldehyde as possible structural formulae. However, C_4H_8OC4H8O may also represent a 5-membered ring, ether tetrahydrofuran:
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THF (so-called) is a solvent that is widely used in organic and organometallic chemistry. It is water soluble, and higher boiling than diethyl ether, and its structure illustrates the richness of organic chemistry: only a few atoms, but a wealth of possible structural formulae.