Organic Chemistry, Books a la Carte Edition (8th Edition)
Organic Chemistry, Books a la Carte Edition (8th Edition)
8th Edition
ISBN: 9780134074580
Author: Bruice, Paula Yurkanis
Publisher: PEARSON
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Chapter 9, Problem 106P

(a)

Interpretation Introduction

Interpretation:

Synthesis of n-pentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pKa = 26) using an appropriate base to generate a carbanion.

The acetylide carbanion is a good nucleophile and can undergo nucleophilic substitution reactions (usually SN2 ) with 1o or 2o alkyl halides (Cl, Br or I) which can produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene (acetylene) H-CC-H can be susbtituted providing access to monosubstituted (H-CC-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-CC-R'

The product is also an alkyne; it can also undergo the other reactions.

(b)

Interpretation Introduction

Interpretation:

Synthesis of 2-pentanone from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pKa = 26) using an appropriate base to generate a carbanion.

The acetylide carbanion is a good nucleophile and can undergo nucleophilic substitution reactions (usually SN2 ) with 1o or 2o alkyl halides (Cl, Br or I) which can produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene (acetylene) H-CC-H can be susbtituted providing access to monosubstituted (H-CC-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-CC-R'

The product is also an alkyne; it can also undergo the other reactions.

(c)

Interpretation Introduction

Interpretation:

Synthesis of Pentanal from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pKa = 26) using an appropriate base to generate a carbanion.

The acetylide carbanion is a good nucleophile and can undergo nucleophilic substitution reactions (usually SN2 ) with 1o or 2o alkyl halides (Cl, Br or I) which can produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene (acetylene) H-CC-H can be susbtituted providing access to monosubstituted (H-CC-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-CC-R'

The product is also an alkyne; it can also undergo the other reactions.

(d)

Interpretation Introduction

Interpretation:

Synthesis of 1, 2-epoxypentane from 1-Bromo propane should be shown.

Concept Introduction:

Target molecule is nothing but the desired product.

Terminal alkynes are unusual for simple hydrocarbons in that they can be deprotonated (pKa = 26) using an appropriate base to generate a carbanion.

The acetylide carbanion is a good nucleophile and can undergo nucleophilic substitution reactions (usually SN2 ) with 1o or 2o alkyl halides (Cl, Br or I) which can produce an internal alkyne.

3o alkyl halides are more likely to undergo elimination.

One or both of the terminal H atoms in ethylene (acetylene) H-CC-H can be susbtituted providing access to monosubstituted (H-CC-R) and symmetrical (R = R') or unsymmetrical (R not equal to R') disubstituted alkynes R-CC-R'

The product is also an alkyne; it can also undergo the other reactions.

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Chapter 9 Solutions

Organic Chemistry, Books a la Carte Edition (8th Edition)

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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