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In a series of seven steps, (S)-malic acid is converted to the bromoepoxide shown on

Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote ISBN: 9781133952848 483

Solution for problem 18.48 Chapter 18

Organic Chemistry | 7th Edition

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Organic Chemistry | 7th Edition | ISBN: 9781133952848 | Authors: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Organic Chemistry | 7th Edition

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Problem 18.48

In a series of seven steps, (S)-malic acid is converted to the bromoepoxide shown on theright in 50% overall yield. This synthesis is enantioselective!of the stereoisomers pos-sible for the bromoepoxide, only one is formed.

Step-by-Step Solution:
Step 1 of 3

CHM 102: Introductory Organic Chemistry Hydrocarbon Alkane is a hydrocarbon that has only single bonds. Alkanes has a general formula of Cn 2n+2. An alkane in the shape of a ring is called a cycloalkane. Alkene is a compound that has at least one double bond. Alkene general formula is n 2n. • Alkyne is a compound that has at least one triple bond. A straight chain alkyne with one triple bond has the formula n 2n − 2 H H H H H H H C H H C C C H H C C H H H H H H H Methane (4H ) Ethane (CH -CH ) Propane (3H 2CH 3CH ) 3 3 H H H H H H H H H H C C C C H H C C C C C H H H H H Butane (CH -CH -CH -CH ) H H H H H 3 2 2 3 Pentane 3CH2-C2 -C2 -3H -CH ) Nomenclature of alkane Identify the parent chain (longest carbon chain) and the substituents (groups attached to the parent chain). Identify the ‘branches’ on the longest carbon chain and name them accordingly. Number the carbon atoms on the longest carbon chain to describe the positions of the branches – use the lowest numbers possible. Each substituent is given a n

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Chapter 18, Problem 18.48 is Solved
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Textbook: Organic Chemistry
Edition: 7
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
ISBN: 9781133952848

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In a series of seven steps, (S)-malic acid is converted to the bromoepoxide shown on