Organic Chemistry
7th Edition
ISBN: 9780321803078
Author: Bruice, Paula Yurkanis
Publisher: Pearson College Div
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Question
Chapter 13.9, Problem 21P
(a)
Interpretation Introduction
Interpretation:
The major product of the reaction of 1-methylcyclohexene with given reagents should be drawn.
(b)
Interpretation Introduction
Interpretation:
For each reaction in part (a) Stereoisomer should be identified.
Concept introduction:
Radical or free radical: unpaired valence electron of an atom, molecule, or ion is called as radical.
Chiral: Four different atoms attached to a carbon atom is called chiral molecule.
Achiral: A molecula has superimposable mirror images are called achiral.
Stereoisomers: Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.
Enantiomers: A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers: A compound which is non-superimposable and non-mirror image is called enantiomers
Racemic mixture: A racemic mixture is simply a mixture containing an equal amount of each enantiomer
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A. Draw the structure(s) of the major product(s) from addition of 1 equivalent of HX to the conjugated diene.
B. Show the correct mechanism using curved arrows
When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed
When 2-bromo-3-phenylbutane is treated with sodium methoxide, two alkenes result (by E2 elimination). The Zaitsevproduct predominates.(a) Draw the reaction, showing the major and minor products.(b) When one pure stereoisomer of 2-bromo-3-phenylbutane reacts, one pure stereoisomer of the major product results.For example, when (2R,3R)-2-bromo-3-phenylbutane reacts, the product is the stereoisomer with the methyl groups cis.Use your models to draw a Newman projection of the transition state to show why this stereospecificity is observed.(c) Use a Newman projection of the transition state to predict the major product of elimination of (2S,3R)-2-bromo-3-phenylbutane
Chapter 13 Solutions
Organic Chemistry
Ch. 13.2 - Prob. 1PCh. 13.2 - Write the steps for formation of...Ch. 13.3 - Prob. 3PCh. 13.4 - Prob. 4PCh. 13.5 - Prob. 7PCh. 13.5 - a. Would chlorination or bromination produce a...Ch. 13.5 - Prob. 10PCh. 13.6 - Prob. 11PCh. 13.7 - Prob. 12PCh. 13.7 - Prob. 13P
Ch. 13.8 - Prob. 14PCh. 13.8 - Draw the stereoisomers of the major...Ch. 13.9 - a. How many stereoisomers are formed from the...Ch. 13.9 - Prob. 17PCh. 13.9 - Prob. 19PCh. 13.9 - Prob. 20PCh. 13.9 - Prob. 21PCh. 13.10 - Prob. 22PCh. 13.11 - How many atoms share the unpaired electrons in...Ch. 13.11 - Prob. 24PCh. 13 - Prob. 25PCh. 13 - Prob. 26PCh. 13 - Prob. 27PCh. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - Prob. 32PCh. 13 - Prob. 33PCh. 13 - Prob. 34PCh. 13 - Prob. 35PCh. 13 - Starting with cyclohexane, how could the following...Ch. 13 - a. Propose a mechanism for the following reaction:...Ch. 13 - What stereoisomers are obtained from the following...Ch. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Draw the products of the following reactions,...Ch. 13 - a. What five-carbon alkene forms the same product...Ch. 13 - Prob. 44PCh. 13 - Prob. 45PCh. 13 - Prob. 46PCh. 13 - Explain why the rate of bromination of methane...Ch. 13 - Prob. 48P
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