Bundle: Organic Chemistry, 9th, Loose-Leaf + OWLv2, 4 terms (24 months) Printed Access Card
9th Edition
ISBN: 9781305701021
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 1.SE, Problem 57AP
Among the most common over-the-counter drugs you might find in a medicine cabinet are mild pain relievers such ibuprofen (Advil, Motrin), naproxen (Aleve), and acetaminophen (Tylenol).
(a) How many sp3-hybridized carbons does each molecule have?
(b) How many sp2-hybridized carbons does each molecule have?
(c) Can you spot any similarities in their structures?
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5. A solution of sucrose is fermented in a vessel until the evolution of CO2 ceases. Then, the
product solution is analyzed and found to contain, 45% ethanol; 5% acetic acid; and 15%
glycerin by weight.
If the original charge is 500 kg, evaluate;
e. The ratio of sucrose to water in the original charge (wt/wt).
f. Moles of CO2 evolved.
g. Maximum possible amount of ethanol that could be formed.
h. Conversion efficiency.
i. Per cent excess of excess reactant.
Reactions:
Inversion reaction: C12H22O11 + H2O →2C6H12O6
Fermentation reaction: C6H12O6 →→2C2H5OH + 2CO2
Formation of acetic acid and glycerin: C6H12O6 + C2H5OH + H₂O→ CH3COOH + 2C3H8O3
Show work. don't give Ai generated solution. How many carbons and hydrogens are in the structure?
13. (11pts total) Consider the arrows pointing at three different carbon-carbon bonds in the
molecule depicted below.
Bond B
2°C. +2°C. cleavage
Bond A
•CH3 + 26.← Cleavage
2°C. +
Bond C
+3°C•
CH3 2C
Cleavage
E
2°C. 26.
weakest bond
Intact molecule
Strongest 3°C 20.
Gund
Largest
argest
a. (2pts) Which bond between A-C is weakest? Which is strongest? Place answers in
appropriate boxes.
C
Weakest
bond
A
Produces
Most
Bond
Strongest
Bond
Strongest Gund
produces least stable
radicals
Weakest
Stable radical
b. (4pts) Consider the relative stability of all cleavage products that form when bonds A,
B, AND C are homolytically cleaved/broken. Hint: cleavage products of bonds A, B,
and C are all carbon radicals.
i. Which ONE cleavage product is the most stable? A condensed or bond line
representation is fine.
13°C. formed in
bound C
cleavage
ii. Which ONE cleavage product is the least stable? A condensed or bond line
representation is fine.
• CH3
methyl radical
Formed in Gund A Cleavage
c.…
Chapter 1 Solutions
Bundle: Organic Chemistry, 9th, Loose-Leaf + OWLv2, 4 terms (24 months) Printed Access Card
Ch. 1.3 - Give the ground-state electron configuration for...Ch. 1.3 - How many electrons does each of the following...Ch. 1.4 - Prob. 3PCh. 1.4 - Convert the following representation of ethane,...Ch. 1.4 - What are likely formulas for the following...Ch. 1.4 - Prob. 6PCh. 1.4 - Prob. 7PCh. 1.7 - Draw a line-bond structure for propane, CH3CH2CH3....Ch. 1.7 - Convert the following molecular model of hexane, a...Ch. 1.8 - Draw a line-bond structure for propene, CH3CH=CH2....
Ch. 1.8 - Draw a line-bond structure for 1, 3-butadiene,...Ch. 1.8 - Following is a molecular model of aspirin...Ch. 1.9 - Draw a line-bond structure for propyne, CH3C≡CH....Ch. 1.10 - Prob. 14PCh. 1.12 - Prob. 15PCh. 1.12 - Prob. 16PCh. 1.12 - The following molecular model is a representation...Ch. 1.SE - Convert each of the following molecular models...Ch. 1.SE - The following model is a representation of citric...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - The following model is a representation of...Ch. 1.SE - How many valence electrons does each of the...Ch. 1.SE - Give the ground-state electron configuration for...Ch. 1.SE - Prob. 24APCh. 1.SE - Prob. 25APCh. 1.SE - Draw an electron-dot structure for acetonitrile,...Ch. 1.SE - Draw a line-bond structure for vinyl chloride,...Ch. 1.SE - Fill in any nonbonding valence electrons that are...Ch. 1.SE - Convert the following line-bond structures into...Ch. 1.SE - Convert the following molecular formulas into...Ch. 1.SE - Prob. 31APCh. 1.SE - Oxaloacetic acid, an important intermediate in...Ch. 1.SE - Prob. 33APCh. 1.SE - Potassium methoxide, KOCH3, contains both covalent...Ch. 1.SE - What is the hybridization of each carbon atom in...Ch. 1.SE - Prob. 36APCh. 1.SE - Prob. 37APCh. 1.SE - What bond angles do you expect for each of the...Ch. 1.SE - Propose structures for molecules that meet the...Ch. 1.SE - What kind of hybridization do you expect for each...Ch. 1.SE - Pyridoxal phosphate, a close relative of vitamin...Ch. 1.SE - Prob. 42APCh. 1.SE - Prob. 43APCh. 1.SE - Quetiapine, marketed as Seroquel, is a heavily...Ch. 1.SE - Tell the number of hydrogens bonded to each carbon...Ch. 1.SE - Why do you suppose no one has ever been able to...Ch. 1.SE - Allene, H2C=C=CH2, is somewhat unusual in that it...Ch. 1.SE - Allene (see Problem 1-47) is structurally related...Ch. 1.SE - Complete the electron-dot structure of caffeine,...Ch. 1.SE - Most stable organic species have tetravalent...Ch. 1.SE - A carbanion is a species that contains a...Ch. 1.SE - Divalent carbon species called carbenes are...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - There are two different substances with the...Ch. 1.SE - Prob. 56APCh. 1.SE - Among the most common over-the-counter drugs you...
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