Organic Chemistry; Organic Chemistry Study Guide A Format: Kit/package/shrinkwrap
Organic Chemistry; Organic Chemistry Study Guide A Format: Kit/package/shrinkwrap
8th Edition
ISBN: 9780134581064
Author: Bruice, Paula Yurkanis
Publisher: Prentice Hall
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Chapter 9, Problem 115P

(a)

Interpretation Introduction

Interpretation:

The products of SN2/E2 reaction of (3S, 4S)-3-bromo-4-methylhexane with methoxide base should be drawn.

Concept Introduction:

For alkyl halide (tertiary, benzylic, and allylic) that can undergo both SN2/E2. and SN1/E1. reaction.

A good nucleophile/strong base favors SN2/E2.

In primary alkyl halides substitution take place.

In secondary alkyl halides substitution and elimination take place (strong. bulky bases and high temperatures favor elimination over substitution).

In tertiary alkyl halides only elimination takes place.

Allylic and benzylic halides substitution and elimination takes place (unless they are tertiary).

Tertiary alkyl halides, allylic halides and benzylic halides: substitution and elimination with substitution favored.

(b)

Interpretation Introduction

Interpretation:

The products of SN2/E2 reaction of (3R, 4R)-3-bromo-4-methylhexane with methoxide base should be drawn.

Concept Introduction:

For alkyl halide (tertiary, benzylic, and allylic) that can undergo both SN2/E2. and SN1/E1. reaction.

A good nucleophile/strong base favors SN2/E2.

In primary alkyl halides substitution take place.

In secondary alkyl halides substitution and elimination take place (strong. bulky bases and high temperatures favor elimination over substitution).

In tertiary alkyl halides only elimination takes place.

Allylic and benzylic halides substitution and elimination takes place (unless they are tertiary).

Tertiary alkyl halides, allylic halides and benzylic halides: substitution and elimination with substitution favored.

(c)

Interpretation Introduction

Interpretation:

The products of SN2/E2 reaction of (3S, 4R)-3-bromo-4-methylhexane with methoxide base should be drawn.

Concept Introduction:

For alkyl halide (tertiary, benzylic, and allylic) that can undergo both SN2/E2. and SN1/E1. reaction.

A good nucleophile/strong base favors SN2/E2.

In primary alkyl halides substitution take place.

In secondary alkyl halides substitution and elimination take place (strong. bulky bases and high temperatures favor elimination over substitution).

In tertiary alkyl halides only elimination takes place.

Allylic and benzylic halides substitution and elimination takes place (unless they are tertiary).

Tertiary alkyl halides, allylic halides and benzylic halides: substitution and elimination with substitution favored.

(d)

Interpretation Introduction

Interpretation:

The products of SN2/E2 reaction of (3R, 4S)-3-bromo-4-methylhexane with methoxide base should be drawn.

Concept Introduction:

For alkyl halide (tertiary, benzylic, and allylic) that can undergo both SN2/E2. and SN1/E1. reaction.

A good nucleophile/strong base favors SN2/E2.

In primary alkyl halides substitution take place.

In secondary alkyl halides substitution and elimination take place (strong. bulky bases and high temperatures favor elimination over substitution).

In tertiary alkyl halides only elimination takes place.

Allylic and benzylic halides substitution and elimination takes place (unless they are tertiary).

Tertiary alkyl halides, allylic halides and benzylic halides: substitution and elimination with substitution favored.

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For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. ? Will the first MgBr product that forms in this reaction create a new CC bond? olo ? OH جمله O Yes Ⓒ No MgCl ? Will the first product that forms in this reaction create a new CC bond? Click and drag to start drawing a structure. Yes No X ☐ : ☐ टे PH
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PROPOSE REACTION MECHANISM FOR ACID-CATALYZED REACTION OF 3-PENTANONE WITH DIMETHYLAMINE

Chapter 9 Solutions

Organic Chemistry; Organic Chemistry Study Guide A Format: Kit/package/shrinkwrap

Ch. 9.2 - Prob. 17PCh. 9.3 - Prob. 18PCh. 9.4 - Prob. 19PCh. 9.5 - Draw the configuration(s) of the substitution...Ch. 9.5 - Which of the following reactions take place more...Ch. 9.7 - Prob. 22PCh. 9.7 - Prob. 23PCh. 9.7 - Prob. 24PCh. 9.7 - Prob. 25PCh. 9.8 - Four alkenes are formed from the E1 reaction of...Ch. 9.8 - If 2-fluoropentane could undergo an E1 reaction,...Ch. 9.8 - Prob. 28PCh. 9.8 - Propose a mechanism for the following reaction:Ch. 9.9 - Prob. 30PCh. 9.9 - What percentage of the reaction described in...Ch. 9.10 - Prob. 33PCh. 9.10 - Prob. 35PCh. 9.11 - Why do cis-1-bromo-2-ethylcyclohexane and...Ch. 9.11 - Which isomer reacts more rapidly in an E2...Ch. 9.11 - Prob. 38PCh. 9.12 - Prob. 39PCh. 9.12 - Prob. 40PCh. 9.12 - Prob. 41PCh. 9.12 - Explain why only a substitution product and no...Ch. 9.12 - a. Explain why 1-bromo-2,2-dimethylpropane has...Ch. 9.13 - Prob. 44PCh. 9.13 - Prob. 45PCh. 9.13 - What products will be obtained from the El...Ch. 9.13 - Prob. 47PCh. 9.13 - Prob. 48PCh. 9.13 - Prob. 49PCh. 9.13 - Why is a cumulated diene not formed in the...Ch. 9.13 - What product is obtained when the following...Ch. 9.13 - What products are formed from the following...Ch. 9.14 - Prob. 54PCh. 9.14 - Prob. 55PCh. 9.14 - Prob. 56PCh. 9.14 - Prob. 58PCh. 9.14 - Under which of the following reaction conditions...Ch. 9.15 - A small amount of another organic product is...Ch. 9.15 - What is the best way to prepare the following...Ch. 9.15 - Prob. 62PCh. 9.15 - What products (including stereoisomers, if...Ch. 9.16 - After a proton is removed from the OH group, which...Ch. 9.16 - Prob. 65PCh. 9.17 - Prob. 66PCh. 9 - Prob. 1PCh. 9 - Methoxychlor is an insecticide that was intended...Ch. 9 - Prob. 67PCh. 9 - Prob. 68PCh. 9 - Prob. 69PCh. 9 - Prob. 70PCh. 9 - Prob. 71PCh. 9 - Prob. 72PCh. 9 - Starting with cyclohexene, how can the following...Ch. 9 - Prob. 74PCh. 9 - The pKa of acetic acid in water is 4.76. What...Ch. 9 - Prob. 76PCh. 9 - Prob. 77PCh. 9 - Prob. 78PCh. 9 - Prob. 79PCh. 9 - Prob. 80PCh. 9 - Prob. 81PCh. 9 - Prob. 82PCh. 9 - Draw the major product obtained when each of the...Ch. 9 - Prob. 84PCh. 9 - a. Indicate how each of the following factors...Ch. 9 - Prob. 86PCh. 9 - A chemist wanted to synthesize the...Ch. 9 - Prob. 88PCh. 9 - Prob. 89PCh. 9 - Prob. 90PCh. 9 - Prob. 91PCh. 9 - Starting with an alkyl halide, how could the...Ch. 9 - Indicate which species in each pair gives a higher...Ch. 9 - Prob. 94PCh. 9 - Rank the following from most reactive to least...Ch. 9 - For each of the following alkyl halides, indicate...Ch. 9 - Prob. 97PCh. 9 - When 2-bromo-2,3-dimethylbutane reacts with a...Ch. 9 - Prob. 100PCh. 9 - When the following compound undergoes solvolysis...Ch. 9 - cis-1-Bromo-4-tert-butylcyclohexane and...Ch. 9 - Draw the substitution and elimination products.Ch. 9 - tert-Butyl chloride undergoes solvolysis in both...Ch. 9 - Prob. 105PCh. 9 - Prob. 106PCh. 9 - In which solventethanol or diethyl etherwould the...Ch. 9 - Prob. 108PCh. 9 - Two bromoethers are obtained from the reaction of...Ch. 9 - Prob. 110PCh. 9 - Prob. 111PCh. 9 - Prob. 112PCh. 9 - Which of the following hexachlorocyclohexanes is...Ch. 9 - Explain why the rate of the reaction of...Ch. 9 - Prob. 115PCh. 9 - Two elimination products are obtained from the...Ch. 9 - Draw the structures or the product of the obtained...Ch. 9 - How could you prepare the following compounds from...Ch. 9 - cis-4-Bromocyclohexanol and...Ch. 9 - Prob. 120PCh. 9 - Propose a mechanism for the following reaction:Ch. 9 - Prob. 122PCh. 9 - Prob. 123PCh. 9 - Prob. 124PCh. 9 - Prob. 125PCh. 9 - Predict the product for the following reaction and...Ch. 9 - Prob. 127PCh. 9 - Prob. 128PCh. 9 - When equivalent amounts of methyl bromide nod...Ch. 9 - Prob. 130PCh. 9 - The reaction of chloromethane with hydroxide ion...
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