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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The oxidation of 3-pentanol to 3-pentanone was performed in the lab and an IR was taken of the finished product.  (a) what are the key functional groups in the starting material, 3-pentaol? (b) what are the key functional groups in the product, 3-pentanone? (c) based on the IR spectrum below, was the experiment successful, and, if so, how pure was the product? Explain your reasoning.
and An acidic liquid has a broad band at 3300 cm a sharp band at 1710 cm in the infrared spectrum. One mole of this unknown reacts with one mole of NaOH. The ¹H NMR spectrum shows three peaks in the ratio 2 : 2 : 1. Microanalysis gave C, 33.2 %; H, 4.6%; C1, 32.7%. Deduce the structure of the unknown. Spell out the full name of the compound.
(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).
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