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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

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

(a)

(b)

(c)

Dimethylamine(CH3) 2 NHhas a molecular weight of 45 and a boiling point of 7.40C. Trimethylamine, (CH3) 3N, has a higher molecular weight (59) but a lower boiling point(3.50C) . Explain this apparent discrepancy.

Question: Show the products you expect when each compound reacts with NBS with light shining on the reaction.

c)

Question:

  1. Why do most long-chain fatty acids show a large peak in the mass spectrum at m/z 60?
  2. Use equations to explain the prominent peaks at m/z 74 and m/z 87 in the mass spectrum of 2-methylpentanoic acid.
  3. Why doesn鈥檛 the mass spectrum of 2-methylpentanoic acid show a large peak at m/z 60?

An unknown compound gives a mass spectrum with a weak molecular ion at m/z113 and a prominent ion at m/z68. Its NMR and IR spectra are shown here. Determine the structure, and show how it is consistent with the observed absorptions. Propose a favorable fragmentation to explain the prominent MS peak at m/z68.

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