LL ORG CHEM
LL ORG CHEM
6th Edition
ISBN: 9781264840083
Author: SMITH
Publisher: MCG
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Chapter 29, Problem 33P
Interpretation Introduction

Interpretation: The stepwise mechanism for the formation of flexibilene from diphosphate and isopentenyl diphosphate is to be drawn. The unusual about the cyclization that forms 15-membered ring of flexibilene is to be stated.

Concept introduction: Terpenes are naturally occurring compounds that are present in plants and animals. Terpenes contain one or more isoprene units. Terpenoids are derivatives of terpenes with oxygen containing functional group such as carbonyl groups. Monoterpenes contain two isoprene units, sesquiterpene contain three isoprene units etc. Terpenes and terpenoids can be biologically synthesized from dimethylallyl diphosphate and isopentenyl diphosphate.

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Part II. two unbranched ketone have molecular formulla (C8H100). El-ms showed that both of them have a molecular ion peak at m/2 =128. However ketone (A) has a fragment peak at m/2 = 99 and 72 while ketone (B) snowed a fragment peak at m/2 = 113 and 58. 9) Propose the most plausible structures for both ketones b) Explain how you arrived at your conclusion by drawing the Structures of the distinguishing fragments for each ketone, including their fragmentation mechanisms.
Part V. Draw the structure of compound tecla using the IR spectrum Cobtained from the compound in KBr pellet) and the mass spectrum as shown below. The mass spectrum of compound Tesla showed strong mt peak at 71. TRANSMITTANCE LOD Relative Intensity 100 MS-NW-1539 40 20 80 T 44 55 10 15 20 25 30 35 40 45 50 55 60 65 70 75 m/z D 4000 3000 2000 1500 1000 500 HAVENUMBERI-11
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