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Chapter 8: Q10P (page 415)

Predict the major products of the following reactions.

(a) Propene + BH3 .THF (b) the product from part (a) + H2O2/OH-

(c) 2-methylpent-2-ene + BH3.THF (d) the product from part (c) + H2O2/OH-

(e) methylcyclohexane+ BH3 .THF (f) the product from (e) + H2O2/OH-

Short Answer

Expert verified

Answer

a.

b.

c.

d.

e.

f.

Step by step solution

01

BH3, THF

a. In hydroboration, borane in presence of tetrahydrofuran solvent gives tri substituted boron compound.

It generally follows anti-markovnikov rule without water. According to this rule hydroxyl group is attached to the more substituted alkenes and hydrogen is attached to the less substituted alkenes.

02

Addition of  H2O2/OH-  

Addition of H2O2/OH- convert this product to alcohol. It is reduction. Hydroxyl ion is used as base.

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Most popular questions from this chapter

Predict the major products of the following reactions, including the stereochemistry.

  1. Cyclohexene + KMnO4, H2O, cold dilute
  2. Cyclohexene + peroxyacetate acid, in water
  3. cis-pent-2-ene + OsO4,H2O2
  4. cis-pent-2-ene + peroxyacetate acid in water
  5. trans-pent-2-ene + OsO4, H2O2
  6. trans-pent-2-ene + peroxyacetic acid in water

The two butenedioic acids are called fumaric acid(trans) and maleic acid(cis). 2,3-Dihydroxybutanedioic acid is called tartaric acid.

Show how would you convert

  1. Fumaric acid to (±)-tartaric acid.
  2. Fumaric acid to meso-tartaric acid.
  3. Maleic acid to (±)-tartaric acid.
  4. Maleic acid to meso-tartaric acid.

Unknown X, C5 H9 Br, does not react with bromine or with dilute KMnO4. Upon treatment with potassium tert-butoxide, X gives only one product, Y, C5 H8. Unlike X, Y decolorizes bromine and changes KMnO4 from purple to brown. Catalytic hydrogenation of Y gives methylcyclobutane. Ozonolysis–reduction of Y gives dialdehyde Z, C5 H8 O2. Propose consistent structures for X, Y, and Z. Is there any aspect of the structure of X that is still unknown?

A graduate student attempted to form the iodohydrin of the alkene shown below. Her analysis of the products showed a good yield of an unexpected product. Propose a mechanism to explain the formation of this product.

Limonene is one of the compounds that give lemons their tangy odour.Show the structures of the products expected when limonene reacts with an excess of each of these reagents.

(a) Borane in tetrahydrofuran, followed by basic hydrogen peroxide

(b) m-chloroperoxybenzoic acid

(c) ozone, then dimethyl sulfide

(d) a mixture of osmic acid and hydrogen peroxide

(e) hot, concentrated potassium permanganate

(f) peroxyacetic acid in acidic water

(g) hydrogen and a platinum catalyst

(h) hydrogen bromide gas

(i) hydrogen bromide gas in a solution containing dimethyl peroxide

(j) bromine water

(k) chlorine gas

(l) mercuric acetate in methanol, followed by sodium borohydride

(m) CHBr3 and 50% aq. NaOH
See all solutions

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