EBK ESSENTIAL ORGANIC CHEMISTRY
EBK ESSENTIAL ORGANIC CHEMISTRY
3rd Edition
ISBN: 8220100659461
Author: Bruice
Publisher: PEARSON
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Chapter 20.6, Problem 11P
Interpretation Introduction

Interpretation:

The isoprene units has to be marked in lycopene and β-carotene and has to detect the similarity in the way which squalene, lycopene and β-carotene are biosynthesized.

Concept Introduction:

Terpenes are made by joining five-carbon units, usually in a head to tail-fashion.

Monoterpenes are those terpenes with two isoprene units-have 10 carbons, sesquiterpenes have 15 carbons, diterpenes have 20 carbons, triterpenes have 30 carbons and tetraterpenes have 40 carbons.

Isopentenyl pyrophosphate (isoprene) is the five-carbon compound used for the biosynthesis of terpenes.

Isoprene unit:

  EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 20.6, Problem 11P , additional homework tip  1

  EBK ESSENTIAL ORGANIC CHEMISTRY, Chapter 20.6, Problem 11P , additional homework tip  2

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Mark off the isoprene units in lycopene and beta-carotene. Can you detect a similarity in the way in which squalene, lycopene, and beta-carotene are biosynthesized?
a-pinene When a-pinene reacts with 1. BH3; 2. H₂O2, NaOH, H₂O 4 possible cis,trans isomers can be formed, but one of these is formed more readily than the others. Draw the structure of this preferred isomer. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • To aid you in your drawing, the structure of a-pinene is provided for you in the drawing palette.
Give the reaction equation for the alkene given to you assuming the reactant was Br2, in the presence ofwater indicating the stereochemistry of all products formed.
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