ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
10th Edition
ISBN: 9781260028355
Author: Carey
Publisher: MCG CUSTOM
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Chapter 8, Problem 57P
Dehydration of
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Problem 22 of 24
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Draw the missing organic structures
in the following multistep synthesis
at physiological pH (pH = 7.4). Ignore
any inorganic byproducts formed.
0
0
ΝΘ
BrCH(CO2CH2CH3)2
Select to Draw
1. NaOCH2CH3 2.
(CH3)2CHCI
Devise electrochemical cells in which the following reactions could be made to occur. If liquid
junctions are necessary, note them in the cell schematic appropriately, but neglect their effects.
(a) H2OH + OH¯
(b) 2H2O2
H₂O
(c) 2PbSO4 + 2H2O
(d) An
TMPD
PыO₂+ Pb + 4H+ + 20%¯¯
An + TMPD (in acetonitrile, where An and An are anthracene and its
anion radical, and TMPD and TMPD are N,N,N',N'-tetramethyl-p-phenylenediamine and its
cation radical. Use anthracene potentials for DMF solutions given in Appendix C.3).
(e) 2Ce3+ + 2H + BQ 2Ce4+ + H2Q (aqueous, where BQ is p-benzoquinone and H₂Q is p-
hydroquinone)
(f) Ag +Agl (aqueous)
(g) Fe3+ + Fe(CN)6 Fe²+ + Fe(CN) (aqueous)
Consider each of the following electrode-solution interfaces, and write the equation for the elec-
trode reaction that occurs first when the potential is moved in (1) a negative direction and (2) a posi-
tive direction from the open-circuit potential. Next to each reaction write the approximate potential
for the reaction in V vs. SCE (assuming the reaction is reversible).
(a) Pt/Cu2+ (0.01 M), Cd2+ (0.01 M), H2SO4(1 M)
(b) Pt/Sn2+ (0.01 M), Sn4+ (0.01 M), HCl(1 M)
(c) Hg/Cd2+ (0.01 M), Zn2+ (0.01 M), HCl(1 M)
Chapter 8 Solutions
ORGANIC CHEMISTRY-PACKAGE >CUSTOM<
Ch. 8.1 - What three alkenes yield 2-methylbutane on...Ch. 8.2 - Prob. 2PCh. 8.2 - Prob. 3PCh. 8.3 - Prob. 4PCh. 8.4 - Prob. 5PCh. 8.4 - Give a structural formula for the carbocation...Ch. 8.5 - Prob. 7PCh. 8.6 - Instead of the three-step process of Mechanism...Ch. 8.6 - The rates of hydration of the two alkenes shown...Ch. 8.6 - Is the electrophilic addition of hydrogen chloride...
Ch. 8.7 - You can calculate the equilibrium constant for the...Ch. 8.7 - Does the presence or absence of a catalyst such as...Ch. 8.7 - The gas phase reaction of ethanol with hydrogen...Ch. 8.8 - Prob. 14PCh. 8.8 - Hydroborationoxidation of -pinene, like its...Ch. 8.10 - Arrange the compounds 2-methyl-1-butene,...Ch. 8.10 - Give the structure of the product formed when each...Ch. 8.11 - Prob. 18PCh. 8.11 - Prob. 19PCh. 8.12 - Prob. 20PCh. 8.12 - Prob. 21PCh. 8.13 - Prob. 22PCh. 8.14 - Prob. 23PCh. 8.14 - Prob. 24PCh. 8 - How many alkenes yield...Ch. 8 - Prob. 26PCh. 8 - Catalytic hydrogenation of...Ch. 8 - Prob. 28PCh. 8 - Prob. 29PCh. 8 - Prob. 30PCh. 8 - Prob. 31PCh. 8 - A single epoxide was isolated in 7984% yield in...Ch. 8 - Prob. 33PCh. 8 - Prob. 34PCh. 8 - On catalytic hydrogenation over a rhodium...Ch. 8 - Prob. 36PCh. 8 - Prob. 37PCh. 8 - Prob. 38PCh. 8 - Prob. 39PCh. 8 - 1-Butene has a higher heat of hydrogenation than...Ch. 8 - Match the following alkenes with the appropriate...Ch. 8 - The heats of reaction were measured for addition...Ch. 8 - Complete the following table by adding + and -...Ch. 8 - Match the heats of hydrogenation (107 kJ/mol,...Ch. 8 - The iodination of ethylene at 25 C is...Ch. 8 - Specify reagents suitable for converting...Ch. 8 - (a) Which primary alcohol of molecular formula...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Identify compounds A and B in the retrosynthesis...Ch. 8 - Prob. 50PCh. 8 - On being heated with a solution of sodium ethoxide...Ch. 8 - Compound A (C7H15Br) is not a primary alkyl...Ch. 8 - Prob. 53PCh. 8 - Prob. 54PCh. 8 - A mixture of three alkenes (A, B, and C) was...Ch. 8 - Reaction of 3,3-dimethyl-1-butene with hydrogen...Ch. 8 - Dehydration of 2,2,3,4,4-pentamethyl-3-pentanol...Ch. 8 - Prob. 58PCh. 8 - East Indian sandalwood oil contains a hydrocarbon...Ch. 8 - Prob. 60PCh. 8 - Prob. 61PCh. 8 - Prob. 62PCh. 8 - Prob. 63PCh. 8 - Prob. 64PCh. 8 - On the basis of the mechanism of acid-catalyzed...Ch. 8 - As a method for the preparation of alkenes, a...Ch. 8 - Which of the following is the most reasonable...Ch. 8 - Prob. 68PCh. 8 - Oxymercuration Concerns about mercurys toxicity...Ch. 8 - Prob. 70DSPCh. 8 - Prob. 71DSPCh. 8 - Prob. 72DSPCh. 8 - Prob. 73DSPCh. 8 - Oxymercuration Concerns about mercurys toxicity...
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