Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 4.14, Problem 4.23P
- a. Compute the heats of reaction for abstraction of a primary hydrogen and a secondary hydrogen from propane by a fluorine radical.
CH3—CH2—CH3 + F· → CH3—CH2—CH2 + HF
CH3 — CH2 — CH3+F· → CH3—CH—CH3 + HF
- b. How selective do you expect free-radical fluorination to be?
- c. What product distribution would you expect to obtain from the free-radical fluorination of propane?
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Ethers can be prepared by reaction of an alkoxide or phenoxide ion with a primary alkyl halide.
Draw the structure of the expected organic product of the reaction of iodomethane with the following alkoxide ion:
CH3
H3C
O Na
You do not have to consider stereochemistry.
You do not have to explicitly draw H atoms.
• Do not include lone pairs in your answer. They will not be considered in the grading.
• Do not include counter-ions, e.g., Na", I, in your answer.
орy вste
ChemDoodle
Determine the one or two steps it takes to get from the starting
material to the product using the reactions found in this chapter.
HC-C
HO,
a.
HC,
HO
CH2-OH
b. СH, — CH—СH,—CH—CH,
ČH,-CH3
CH2
||
CH3-CH-CH,-Ĉ-CH3
ČH,-CH3
Br
c. CH;-CH,-C=CH2
CH,-CH,-C-CH;
ČH3
7.
The reaction of methoxide anion with
bromoethane to yield the ether ethyl methyl ether and
the bromide anon (Br-) is an excellent example of a
general reaction type called Sy2 (substitution
nucleophilic bimolecular):
CH,0+ CH,СH-Br a CH3-0-CH,СH; + Br-
a. Change in enthalpy is -103 kJ/mol; the change in
entropy is + 0.025 kJ/mol-K. Calculate DG at
300K.
b. Is the reaction endergonic or exergonic?
c. Is the reaction endothermic or exothermic?
d. Use curved arrows to show the complete
mechanism.
Reaction of 2-methyl-1-butene with H-Cl could
yield TWO alkyl chloride products. Draw and name
8.
them.
Chapter 4 Solutions
Organic Chemistry (9th Edition)
Ch. 4.3A - Draw Lewis structures for the following free...Ch. 4.3B - a. Write the propagation steps leading to the...Ch. 4.3C - Prob. 4.3PCh. 4.3C - Prob. 4.4PCh. 4.4 - The following reaction has a value of G =...Ch. 4.4 - Under base-catalyzed conditions two molecules of...Ch. 4.5B - When ethene is mixed with hydrogen in the presence...Ch. 4.5B - For each reaction, estimate whether S for the...Ch. 4.7 - a. Propose a mechanism for the free radical...Ch. 4.7 - a. Using bond-dissociation enthalpies from...
Ch. 4.8 - The reaction of tert-butyl chloride with methanol...Ch. 4.8 - Under certain conditions, the bromination of...Ch. 4.8 - When a small piece of plat num is added to a...Ch. 4.10 - Prob. 4.14PCh. 4.10 - Prob. 4.15PCh. 4.12 - The bromination of methane proceeds through the...Ch. 4.12 - a. Using me BDEs in Table4-2 (page 167 ), compute...Ch. 4.13A - What would be the product ratio in the...Ch. 4.13A - Classify each hydrogen atom in the following...Ch. 4.13B - Use the bond-dissociation enthalpies in Tabte4-2...Ch. 4.13B - Prob. 4.21PCh. 4.13B - Prob. 4.22PCh. 4.14 - a. Compute the heats of reaction for abstraction...Ch. 4.14 - 2,3-Dimethylbutane reacts with bromine in the...Ch. 4.14 - Prob. 4.25PCh. 4.15 - Prob. 4.26PCh. 4.15 - Prob. 4.27PCh. 4.16A - Prob. 4.28PCh. 4.16A - Prob. 4.29PCh. 4.16B - Prob. 4.30PCh. 4.16C - Prob. 4.31PCh. 4.16C - Acetonitrile (CH3C N) is deprotonated by very...Ch. 4.16D - Prob. 4.33PCh. 4 - The following reaction is a common synthesis used...Ch. 4 - Consider the following reaction-energy diagram. a....Ch. 4 - Draw a reaction-energy diagram for a one-step...Ch. 4 - Draw a reaction-energy diagram for a two-step...Ch. 4 - Prob. 4.38SPCh. 4 - Treatment of tert-butyl alcohol with concentrated...Ch. 4 - Label each hydrogen atom in the following...Ch. 4 - Prob. 4.41SPCh. 4 - Prob. 4.42SPCh. 4 - Prob. 4.43SPCh. 4 - Prob. 4.44SPCh. 4 - Prob. 4.45SPCh. 4 - Prob. 4.46SPCh. 4 - For each compound, predict the major product of...Ch. 4 - When exactly 1 mole of methane is mixed with...Ch. 4 - Prob. 4.49SPCh. 4 - Prob. 4.50SPCh. 4 - Prob. 4.51SPCh. 4 - When dichloromethane is treated with strong NaOH,...Ch. 4 - Prob. 4.53SPCh. 4 - When a small amount of iodine is added to a...Ch. 4 - Prob. 4.55SPCh. 4 - When healthy, Earths stratosphere contains a low...Ch. 4 - Prob. 4.57SPCh. 4 - lodination of alkanes using iodine (I2) is usually...
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