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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Textbook Question
Chapter 1.SE, Problem 50AP
Most stable organic species have tetravalent carbon atoms, but species with trivalent carbon atoms also exist. Carbocations are one such class of compounds.
(a) How many valence electrons does the positively charged carbon atom have?
(b) What hybridization do you expect this carbon atom to have?
(c) What geometry is the carbocation likely to have?
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Solution
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Use retrosynthetic analysis to suggest two paths to synthesize 2-methyl-3-hexanol using the Grignard reaction. (Click and drag
the appropriate image to the correct position in the reactions.)
Route 1
Aldehyde 1
or
+98
Aldehyde 2
Route 2
Q6
+100
Solved in 1 attempt
Q7
+95
Solved in 2 attempts
Q8
+98
Unlimited attempts
possible
+
+
Grignard 1
OH
H3O+
Grignard 2
Answer Bank
Q9
+90
MgBr
Unlimited attempts
possible
CH3CH2CH2MgBr
Q10
Unlimited attempts
Q11
?
?
+100
in 1 attempt
2-methyl-3-hexanol
CH3CH2MgBr
H
H
о
H
Attempt 3
2) (4 pt) After the reaction was completed, the student collected the following data. Crude
product data is the data collected after the reaction is finished, but before the product
is purified. "Pure" product data is the data collected after attempted purification using
recrystallization.
Student B's data:
Crude product data
"Pure"
product data
after
recrystallization
Crude mass: 0.93 g grey solid
Crude mp: 96-106 °C
Crude % yield:
Pure mass: 0.39 g white solid
Pure mp: 111-113 °C
Pure % yield:
a) Calculate the crude and pure percent yields for the student's reaction.
b) Summarize what is indicated by the crude and pure melting points.
Don't used hand raiting
Chapter 1 Solutions
Study Guide with Student Solutions Manual for McMurry's Organic Chemistry, 9th
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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