Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Textbook Question
Chapter 2, Problem 41P
In each of the following groups of compounds, identify the one with the largest heat of
combustion and the one with the smallest. (Try to do this problem without consulting
Table 2.3.)
Hexane, heptane, octane
Pentane, 3-methylpentane,
Ethylcyclopentane, ethylcyclohexane, ethylcycloheptane
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Organic Chemistry
Maxwell
presented by Macmillan Learning
(a) Given the reactions and overall heats of combustion of four cyclic rings, calculate the heat of combustion per CH₂ group.
AH for reaction (kJ/mol) AH per CH₂ group (kJ/mol)
-2091
?
-2744
?
-3320
?
-3952
?
Compound
cyclopropane C₂H + 2/0₂
cyclobutane C₂H₂ + 60₂ →
4 8
Combustion reaction
2
2
cyclopentane C₂H₁0 + 15-0₂
cyclohexane C6H₁2 +90₂
12
AH per CH₂ for cyclopropane:
AH per CH₂ for cyclopentane:
+ 3CO, +3H,O
4 CO₂ + 4H₂O
5 CO₂ + 5H2₂O
6CO₂ + 6H₂O
kJ/mol
kJ/mol
(b) Rank the four cycloalkanes in order of stability from least
stable to most stable.
AH per CH₂ for cyclobutane:
AH per CH₂ for cyclohexane:
Least stable
kJ/mol
kJ/mol
B. II
OC. III
QUESTION 6
Consider 2-methylbutane (isopentane). Sighting along the C2-C3 bond, Draw a Newman projection formula for the
most stable conformation. Based on your drawing,
determine the total strain energy for this conformation.
Given the following strain energies with respect to atoms/groups bonded to C-C (one atom/group bonded to each C)
H H eclipsed: 4 kJ/mol
CH3 H eclipsed: 6 kJ/mol
CH3 CH3 eclipsed: 11 kJ/mol
CH3 CH3 gauche staggered: 3.8 kJ/mol
OA 14.8 kJ/mol
OB. 7.6 kJ/mol
O C.3.8 kJ/mol
OD. 11.4 kJ/mol
QUESTION 3
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Rank the following compounds in order of increasing heat of combustion. Be sure to answer all parts.
Drag each item to the correct box.
A) butane
A
Lowest Heat of Combustion
☐ ?
B) pentane
B
с
C) hexane
Highest Heat of Combustion
Chapter 2 Solutions
Organic Chemistry - Standalone book
Ch. 2.4 - Prob. 1PCh. 2.7 - Prob. 2PCh. 2.8 - Identify the orbital overlaps of all of the bonds...Ch. 2.9 - The hydrocarbon shown, called vinylacetylene, is...Ch. 2.12 - Prob. 5PCh. 2.12 - Prob. 6PCh. 2.13 - Prob. 7PCh. 2.14 - Refer to Table 2.2 as needed to answer the...Ch. 2.15 - Prob. 9PCh. 2.15 - Prob. 10P
Ch. 2.16 - Prob. 11PCh. 2.17 - Prob. 12PCh. 2.18 - Prob. 13PCh. 2.20 - Prob. 14PCh. 2.21 - Match the boiling points with the appropriate...Ch. 2.22 - Write a balanced chemical equation for the...Ch. 2.22 - Using the data in Table 2.3, estimate the heat of...Ch. 2.22 - Prob. 18PCh. 2.22 - Prob. 19PCh. 2.23 - Prob. 20PCh. 2.23 - Which of the following reactions requires an...Ch. 2 - The general molecular formula for alkanes is...Ch. 2 - Prob. 23PCh. 2 - Prob. 24PCh. 2 - Prob. 25PCh. 2 - What is the hybridization of each carbon in...Ch. 2 - Prob. 27PCh. 2 - Does the overlap of two p orbitals in the fashion...Ch. 2 - Prob. 29PCh. 2 - Aphids secrete an alarm pheromone having the...Ch. 2 - All the parts of this problem refer to the alkane...Ch. 2 - Prob. 32PCh. 2 - Prob. 33PCh. 2 - Prob. 34PCh. 2 - From among the 18 constitutional isomers of C8H18,...Ch. 2 - Give the IUPAC name for each of the following...Ch. 2 - Using the method outlined in Section 2.16, give an...Ch. 2 - Prob. 38PCh. 2 - Write a balanced chemical equation for the...Ch. 2 - The heats of combustion of methane and butane are...Ch. 2 - In each of the following groups of compounds,...Ch. 2 - Given H for the reaction H2(g)+12O2(g)H2O(l)...Ch. 2 - Prob. 43PCh. 2 - Prob. 44PCh. 2 - Prob. 45PCh. 2 - Prob. 46PCh. 2 - Prob. 47PCh. 2 - Compound A undergoes the following reactions:...Ch. 2 - Prob. 49PCh. 2 - Some Biochemical Reactions of Alkanes Alkanes...Ch. 2 - Prob. 51DSPCh. 2 - Some Biochemical Reactions of Alkanes Alkanes...Ch. 2 - Prob. 53DSP
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