Organic Chemistry
Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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Chapter 23, Problem 3LGP
Interpretation Introduction

Interpretation:

On the basis of given information, the structures of the required terpene and its isoprene unit are to be elucidated.

Concept introduction:

Terpenes are largely found as constituents of essential oils. They are mostly hydrocarbons.

The building block is a five-carbon isoprene unit (CH2C(CH3)CHCH2). The formula of terpene hydrocarbons is (C5H8)n.

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(d) Ozonolysis of 3,4-dimethyl-3-hexene gives compound D. (i) Write the reaction step for the formation of D by including the appropriate reagents. (ii) The mass spectrum of compound D shows a fragment ion peak at m/z 57. Propose the structure of this fragment ion. (ii) Identify the more stable resonance of the proposed structure in (ii).
Name the following compounds A and B. How could you distinguish these two molecules by using 1H NMR and IR techniques? Propose an analytical technique to determine the iron content of these compounds. Calculate the mass percentages of C and H of compound B (C: 12.01 g/mol; H: 1.008 g/mol; Fe: 55.845 g/mol).
Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm−1, and gives the following 1H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 20.
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