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tekilochka [14]
3 years ago
13

(a) How many stereoisomers are possible for 4-methyl-1,2-cyclohexanediol? ___ (b) Name the stereoisomers formed by oxidation of

(S)-4-methylcyclohexene with osmium tetroxide. If there is only one stereoisomer formed, leave the second space blank. Isomer #1: Isomer #2: (c) Is the product formed in step (b) optically active? _____

Chemistry
1 answer:
nataly862011 [7]3 years ago
6 0

Answer:

See explanation

Explanation:

For the first part of the question, we have to check the <u>chiral carbons</u> in 4-methyl-1,2-cyclohexanediol. In this case carbons, <u>1 and 2 are chiral</u>, if we have 2 chiral carbons we will have 4 isomers. We have to remember that formula 2^n in which "n" is the number of chiral carbons, so:

<u>2^n = 2^2 = 4 isomers</u>

<u>And the isomers that we can have are:</u>

1) (1R,2S)-4-methylcyclohexane-1,2-diol

2) (1S,2S)-4-methylcyclohexane-1,2-diol

3) (1S,2S)-4-methylcyclohexane-1,2-diol

4) (1S,2R)-4-methylcyclohexane-1,2-diol

See figure 1

For the second part of the question, we have to remember that the oxidation with OsO_4 is a <u>syn addition</u>. In other words, the "OHs" are added in the <u>same plane</u>. In this case, we have the methyl group with a wedge bond, so the "OH" groups will have a dashed bond due to the <u>steric hindrance</u>. Due to this we only can have <u>1 isomer</u> ((1S,2R,4S)-4-methylcyclohexane-1,2-diol). Finally, on this molecule, <u>we dont have any symmetry planes</u> (this characteristic will cancel out the optical activity), so <u>the product of this reaction has optical activity</u>.

See figure 2

I hope it helps!

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