Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
9th Edition
ISBN: 9781305082144
Author: John E. McMurry
Publisher: Cengage Learning
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Question
Chapter 20.7, Problem 13P
Interpretation Introduction
a)
Interpretation:
How 3-pentanone can be prepared from a nitrile is to be shown.
Concept introduction:
The nitriles can be converted into a
To Show:
How to prepare 3-pentanone from a nitrile.
Interpretation Introduction
b)
Interpretation:
How p-nitroacetophenone can be prepared from a nitrile is to be shown.
Concept introduction:
The nitriles can be converted into a ketone first by treating it with a Grignard reagent and the hydrolyzing the imine-anion formed with water.
To Show:
How to prepare p-nitroacetophenone from a nitrile.
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19.78 Write the products of the following sequences of reactions. Refer to your reaction road-
maps to see how the combined reactions allow you to "navigate" between the different
functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18
roadmaps along with your new Chapter 19 roadmap for these.
(a)
1. BHS
2. H₂O₂
3. H₂CrO4
4. SOCI₂
(b)
1. Cl₂/hv
2. KOLBU
3. H₂O, catalytic H₂SO4
4. H₂CrO4
Reaction
Roadmap
An alkene 5. EtOH
6.0.5 Equiv. NaOEt/EtOH
7. Mild H₂O
An alkane
1.0
2. (CH3)₂S
3. H₂CrO
(d)
(c)
4. Excess EtOH, catalytic H₂SO
OH
4. Mild H₂O*
5.0.5 Equiv. NaOEt/EtOH
An alkene 6. Mild H₂O*
A carboxylic
acid
7. Mild H₂O*
1. SOC₁₂
2. EtOH
3.0.5 Equiv. NaOEt/E:OH
5.1.0 Equiv. NaOEt
6.
NH₂
(e)
1. 0.5 Equiv. NaOEt/EtOH
2. Mild H₂O*
Br
(f)
i
H
An aldehyde
1. Catalytic NaOE/EtOH
2. H₂O*, heat
3. (CH,CH₂)₂Culi
4. Mild H₂O*
5.1.0 Equiv. LDA
Br
An ester
4. NaOH, H₂O
5. Mild H₂O*
6. Heat
7.
MgBr
8. Mild H₂O*
7. Mild H₂O+
Li+ is a hard acid. With this in mind, which if the following compounds should be most soluble in water?
Group of answer choices
LiBr
LiI
LiF
LiCl
Q4: Write organic product(s) of the following reactions and show the curved-arrow mechanism
of the reactions.
Br
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OSO2CH3
MeOH
Chapter 20 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
Ch. 20.1 - Give IUPAC names for the following compounds:Ch. 20.1 - Draw structures corresponding to the following...Ch. 20.2 - Prob. 3PCh. 20.2 - The Ka for dichloroacetic acid is 3.32 Ă— 10-2....Ch. 20.3 - Calculate the percentages of dissociated and...Ch. 20.4 - Which would you expect to be a stronger acid, the...Ch. 20.4 - Dicarboxylic acids have two dissociation...Ch. 20.4 - The pKa of p-cyclopropylbenzoic acid is 4.45. Is...Ch. 20.4 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.6 - Prob. 11PCh. 20.6 - How might you carry out the following...Ch. 20.7 - Prob. 13PCh. 20.7 - Prob. 14PCh. 20.8 - Cyclopentanecarboxylic acid and...Ch. 20.8 - Prob. 16PCh. 20.SE - Prob. 17VCCh. 20.SE - Prob. 18VCCh. 20.SE - The following carboxylic acid can’t be prepared...Ch. 20.SE - Electrostatic potential maps of anisole and...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Predict the product(s) and provide the mechanism...Ch. 20.SE - Prob. 23MPCh. 20.SE - Predict the product(s) and provide the complete...Ch. 20.SE - Acid-catalyzed hydrolysis of a nitrile to give a...Ch. 20.SE - Prob. 26MPCh. 20.SE - Naturally occurring compounds called cyanogenic...Ch. 20.SE - 2-Bromo-6, 6-dimethylcyclohexanone gives 2,...Ch. 20.SE - Naturally occurring compounds called terpenoids,...Ch. 20.SE - In the Ritter reaction, an alkene reacts with a...Ch. 20.SE - Give IUPAC names for the following compounds:Ch. 20.SE - Prob. 32APCh. 20.SE - Prob. 33APCh. 20.SE - Prob. 34APCh. 20.SE - Prob. 35APCh. 20.SE - Prob. 36APCh. 20.SE - Prob. 37APCh. 20.SE - Prob. 38APCh. 20.SE - Calculate the Ka's for the following acids: (a)...Ch. 20.SE - Thioglycolic acid, HSCH2CO2H, a substance used in...Ch. 20.SE - Prob. 41APCh. 20.SE - Prob. 42APCh. 20.SE - How could you convert butanoic acid into the...Ch. 20.SE - How could you convert each of the following...Ch. 20.SE - How could you convert butanenitrile into the...Ch. 20.SE - How would you prepare the following compounds from...Ch. 20.SE - Prob. 47APCh. 20.SE - Using 13CO2 as your only source of labeled carbon,...Ch. 20.SE - Prob. 49APCh. 20.SE - Which method-Grignard carboxylation or nitrile...Ch. 20.SE - Prob. 51APCh. 20.SE - Prob. 52APCh. 20.SE - Propose a structure for a compound C6H12O2 that...Ch. 20.SE - Prob. 54APCh. 20.SE - How would you use NMR (either 13C or 1H) to...Ch. 20.SE - Prob. 56APCh. 20.SE - A chemist in need of 2,2-dimethylpentanoic acid...Ch. 20.SE - Prob. 58APCh. 20.SE - Prob. 59APCh. 20.SE - Prob. 60APCh. 20.SE - Prob. 61APCh. 20.SE - Prob. 62APCh. 20.SE - Prob. 63APCh. 20.SE - The following pKa values have been measured....Ch. 20.SE - Identify the missing reagents a-f in the following...Ch. 20.SE - Propose a structure for a compound, C4H7N, that...Ch. 20.SE - Prob. 67APCh. 20.SE - The 1H and 13C NMR spectra below belong to a...Ch. 20.SE - Propose structures for carboxylic acids that show...Ch. 20.SE - Carboxylic acids having a second carbonyl group...
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