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Chapter 20: Q11P (page 1038)

Circle the isoprene units in geranial, menthol, camphor, and abietic acid.

Short Answer

Expert verified

Terpenes contain a variety of functional groups. Isoprene units in terpenes usually bond head to tail. Isoprene is 2-methyl-1,3-butadiene unit. In geranial, there are two isoprene units and in menthol, there are also two isoprene units. They are both monoterpenes.

Step by step solution

01

Step-1. Isoprene units in geranial and menthol:

Terpenes contain a variety of functional groups. Isoprene units in terpenes usually bond head to tail. Isoprene is 2-methyl-1,3-butadiene unit. In geranial, there are two isoprene units and in menthol, there are also two isoprene units. They are both monoterpenes.

02

Step-2. Isoprene units in camphor and abietic acid:

Terpenes are naturally occurring compounds which are derived from 5-carbon alkene known as isoprene. They contain multiples of five carbon atoms, that is, 10, 15, 20 and so on. Camphor is a monoterpene and contain two isoprene units whereas abietic acid is diterpene and contains four isoprene units.

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Most popular questions from this chapter

Most of the Fischer esterification mechanism is identical with the mechanism of acetal formation. The difference is in the final step, where a resonance-stabilized carbocation loses a proton to give the ester. Write mechanisms for the following reactions, with the comparable steps directly above and below each other. Explain why the final step of the esterification (proton loss) cannot occur in acetal formation, and show what happens instead.

Use the information in Table 4-2 to rank the following radicals in decreasing order of stability.

Q. 15 Show how Fischer esterification might be used to form the following esters. In each case, suggest a method for driving the reaction to completion.

  1. methyl salicylate
  2. methyl formate (bp 32oC )
  3. ethyl phenylacetate

Question. A student adds NBS to a solution of 1-methylcyclohexene and irradiates the mixture with a sunlamp until all the NBS has reacted. After a careful distillation, the product mixture contains two major products of formula.

  1. Draw the resonance forms of the three possible allylic free radical intermediates.
  2. Rank these three intermediates from most stable to least stable.
  3. Draw the products obtained from each free-radical intermediate.

The 2000 Nobel Prize in Chemistry was awarded for work on polyacetylenes. Acetylene can be polymerized using a Ziegler-Natta catalyst. The cis or trans stereochemistry of the products can be controlled by careful selection and preparation of the catalyst. The resulting polyacetylene is an electrical semiconductor with a metallic appearance. cis-Polyacetylene has a copper color, and trans-polyacetylene is silver.

(a) Draw the structures of cis- and trans-polyacetylene.

(b) Use your structures to show why these polymers conduct electricity.

(c) It is possible to prepare polyacetylene films whose electrical conductivity is anisotropic. That is, the conductivity is higher in some directions than in others. Explain how this unusual behavior is possible.
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