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Chapter 10: Q.27. (page 414)

Question: Draw the products formed when each alkene is treated with BH3followed by H2O2,HO-. Include the stereochemistry at all stereogenic centers.

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01

 Step 1:Hydroboration-oxidation reaction

This reaction consists of two steps: hydroboration and oxidation. It gives a racemic mixture of alcohols.

02

Formation of products for a, b and c

a.

The reaction of but-1-ene with BH3followed by oxidation is shown below:

Product formation in a

b.

The reaction of (S)-1,4-dimethylcyclohex-1-ene with BH3 followed by oxidation is shown below:

Product formation in b

c.

The reaction of 1-ethylcyclopent-1-ene with BH3 followed by oxidation is shown below:

Product formation in c

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Most popular questions from this chapter

Question: Draw the constitutional isomer formed in each reaction.

a.

b.

c.

d.

e.

f.

Question: Draw the products formed when (CH3)2C=CH2 is treated with each reagent.

a. HBr

b.H2O, H2SO4

c. CH3CH2HO,H2SO4

d. Cl2

e.Br2 ,H2O

f. NBS (aqueous DMSO)

g. [1] BH3; [2] H2O2 ,HO-

Question: 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?

Question: Label each C-C double bond as E or Z. Kavain is a naturally occurring relaxant isolated from kava root.

Question: (a) Label the carbon–carbon double bond in A as E or Z. (b) Draw the products (including stereoisomers) formed when A is treated with H2O in the presence of H2SO4.
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