When (Z)-3-methyl-3-hexene undergoes hydroboration-oxidation, two isomeric products are formed. Give their structures, and label each chiral carbon atom as (R) or (S).

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06-12-2022
Chemistry

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When (Z)-3-methyl-3-hexene undergoes hydroboration-oxidation, two isomeric products are formed. Give their structures, and label each chiral carbon atom as (R) or (S).

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durbansa43 durbansa43 · Answer 1 · 2022-12-17T22:11:20-05:00

During hydroboration-oxidation of (Z)-3-methyl-3-hexene, two isomeric products are formed: 3-methyl-2-hexanol and 3-methylhexanal. The structures are shown as follows

3-methyl-2-hexanol:

H H

| |

C C

| |

C C

| |

H H

\ |

C C

| |

C C

| |

H H

| |

C C

| |

H H

| |

C C

| |

H H

| |

C C

| |

H H

3-methylhexanal:

H H

| |

C C

| |

C C

| |

H H

\ |

C C

| |

C C

| |

H H

| |

C C

| |

H H

| |

C C

| |

H H

| |

C C

| |

H H

The chiral carbon atoms in these two compounds are labeled as follows:

3-methyl-2-hexanol:

H H

| |

C C

| |

C C

| |

H H

\ |

C C

| |

C(R) C(S)

| |

H H

| |

C C

| |

H H

| |

C C

| |

H H

3-methylhexanal:

H H

| |

C C

| |

C C

| |

H H

\ |

C C

| |

C(S) C(R)

| |

H H

| |

C C

| |

H H

| |

C C

| |

H H

C C

| |

H H

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