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One of the principal components of lemongrass oil is limonene, . When limonene is treated with excess hydrogen and a platinum catalyst, the product is an alkane of formula . What can you conclude about the structure of limonene?

Short Answer

Expert verified

Limonene must have one ring and two double bonds or a triple bond.

Step by step solution

01

Limonene

Limonene has three degrees of unsaturation. Hydrogenation reaction has proved this, as upon catalytic hydrogenation, that is, treatment of limonene with excess hydrogen and platinum as a catalyst, the product gets formed which has only one degree of unsaturation.

02

Structure of Limonene

Two degrees of unsaturation have been removed by hydrogenation reaction, and these must be two double bonds or one triple bond. The remaining unsaturation must be a ring. Thus, limonene must have one ring and either two double bonds or one triple bond.

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Most popular questions from this chapter

One of the principal components of lemongrass oil is limonene, C10H16. When limonene is treated with excess hydrogen and a platinum catalyst, the product is an alkane of formulaC10H20. What can you conclude about the structure of limonene?

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

Show how you would accomplish each of the following synthetic conversions.

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-

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
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