Question 26.Int.1: An acyclic organic compound with the formula C6H12O is found...
An acyclic organic compound with the formula C_6H_{12}O is found to be optically active, does not decolorize Br_2 (in CCl_4), and does not undergo reaction when treated with a mixture of Na_2Cr_2O_7 and H_2SO_4. However, a reaction does occur when the compound is treated with NaBH_4. Identify a compound having these physical and chemical properties. Then draw structures for the two stereoisomers, using dashed and solid wedge symbols. Finally, give acceptable names for the two stereoisomers.
Analyze
There is only one oxygen atom per molecule, so the compound must be an alcohol, ether, aldehyde, or ketone. Also, because there are only 12 hydrogen atoms per molecule, rather than 2 × 6 + 2 = 14, we know that the molecule must contain either a π bond or a ring. We are told the compound is acyclic, and thus the molecule must contain a π bond and not a ring. Alcohols (except tertiary alcohols) and aldehydes are rather easily oxidized, so we suspect the molecule is neither an alcohol (though possibly a tertiary alcohol) nor an aldehyde. The ether linkage is stable in the presence of most oxidizing and reducing agents, and because the compound we need can be reduced, we suspect that that the compound is not an ether. At this point, we must decide whether the molecule is a ketone or a tertiary alcohol containing a carbon-carbon double bond. We can rule out a carbon-carbon double bond because the compound does not react with Br_2, a reaction characteristic of alkenes. The compound we seek is a ketone.
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