Asked Dec 26, 2019

(a) Which diastereomer of oct-4-ene yields a mixture of two enantiomers, (4R,5R)- and (4S, 5S)-4,5-dibromooctane on reaction with Br2? (b) Which diastereomer of oct-4-ene yields a single meso compound, (4R, 5S)-4,5-dibromooctane?


Expert Answer

Step 1

In organic chemistry, different types of chemical reactions are possible on the basis of their mechanism. Some common mechanism are substitution reaction, addition reaction, elimination reaction and rearrangement reactions.

Step 2

The addition of halogen on C=C is an example of addition reactions as each halogen atom is added on double bonded C atoms to form dihalo-products. The addition of halogen on C=C is always anti-addition in which once halogen added to C=C and form an adduct on which another halogen attack in anti-position.


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Br: ô+, :Br : Br: :Br: Br H Hc-CuR Heuc- н 'н н н* н н" н Br Product Alkene Intermediate

Step 3

Part (a) Diastereomer of oct-4-ene yields a mixture of two enantiomers, (4R,5R)- and (4S, 5S)-4,5-dibromooctane on reaction with Br...


Image Transcriptionclose

CH3 CH3 Br Br н Br2 ну Br Br H3C НаС CH3 H3C (4S,5S)-4,5-dibromooctane (4R,5R)-4,5-dibromooctane cis-4-octene


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