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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 from each compound. You may use any necessary reagents.

(a)octan - 1 - ol

(b)non - 1 - ene

(c)oct - 1 - yne

(d)1 - bromoheptane

(e)1 - bromohexane

(f)octanoic鈥�鈥�acid

(g)ethyl鈥�鈥�octanoate

Classify each hydrogen atom in the following compounds as primary (10),secondary(20) , or tertiary(30).

(a) butane

(b) isobutane

(c) 2-methylbutane

(d) cyclohexane

(e) norbornane (bicyclo heptane)

Question: Oxidation of primary alcohol to an aldehyde usually gives some over-oxidation to the carboxylic acid. Assume you have used PCC to oxidize pentan-1-ol to pentanal.

  1. Show how you would use acid-base extraction to purify the pentanal.
  2. Which of the expected impurities cannot be removed from pentanal by acid-base extractions? How would you remove this impurity?

Show how you would synthesize the following compounds, starting with acetylene and any compounds containing no more than four carbon atoms.

(a)hex-1-yne

(b)hex-2-yne

(c)cis-hex-2-ene

(d)trans-hex-2-ene

(e)1,1-dibromohexane

(f)2,2-dibromohexane

(g)pentanal, CH3CH2CH2CH2CHO

(h)pentan-2-one, CH3-CO-CH 2CH2 CH3

(i) (+/)-3,4-dibromohexane

(j)meso-butan-2,3-diol

(k)2-methylhex-3-yn-2-ol

Predict the major products formed when the following amines undergo exhaustive methylation, treatment with Ag2O, and heating.

  1. Hexan-2-amine
  2. 2-methylpiperidine
  3. N-ethylpiperidine

5.

6.
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