Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 9.9F, Problem 9.20P
(a)
Interpretation Introduction
To determine: The structure of the product and an intermediate, when hydroboration-oxidation is applied to
Interpretation: The structure of the product and an intermediate, when hydroboration-oxidation is applied to
Concept introduction: Hydroboration-oxidation reactions convert an
(b)
Interpretation Introduction
To determine: The reason as to why a mixture of products should be expected with any unsymmetrical internal alkyne.
Interpretation: The reason as to why a mixture of products should be expected with any unsymmetrical internal alkyne is to be stated.
Concept introduction: Hydroboration-oxidation reactions convert an alkyne molecule into ketone in the presence of disiamylborane and hydrogen peroxide through two step mechanism, whereas an alkene molecule in hydroboration-oxidation reaction is converted into alcohol by the addition of water.
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b) In order to synthesis 2-phenylpropan-2-ol, you started with a hydration of prop-1-ene
using the hydroboration method. Then you oxidized the intermediate with KMNO4.
Finally, alkylation using CeHsMgBr was performed to obtain the final product. However,
the reaction was not successful. Analyse the reaction by explaining what happened to
the reaction and provide the correct synthetic method.
9. Identify the major product of each reaction and indicate whether the reaction is likely
to proceed by a bimolecular (SN2) or a unimolecular (SN1) mechanism. Why is each
reaction likely to proceed via the mechanism you have chosen? (Hint: The leaving
groups -OSO2CF3 and -OMs are also sulfonates (like tosylate, -OTS), so they are
also good leaving groups.)
a)
b)
d)
Oso₂CF,
OMs
Br
Nal
acetone
NaCN
DMF
CH₂OH
80% H₂O, 20% ethanol
-6-
The second-order rate constant (in units of M-1s-1) for acid-catalyzed hydration at 25 °C is given for each of the following alkenes:
a.Calculate the relative rates of hydration of the alkenes. (Hint: Divide each rate constant by the smallest rate constant of the series: 3.51 x 10-8.)
b. Why does (Z)-2-butene react faster than (E)-2-butene?
c. Why does 2-methyl-2-butene react faster than (Z)-2-butene?
d. Why does 2,3-dimethyl-2-butene react faster than 2-methyl-2-butene?
Chapter 9 Solutions
Organic Chemistry (9th Edition)
Ch. 9.1 - a. Count the elements of unsaturation in...Ch. 9.2 - Prob. 9.2PCh. 9.4B - What reaction would acetylene likely undergo if it...Ch. 9.6 - Prob. 9.4PCh. 9.6 - Predict the products of the following acid-base...Ch. 9.7A - Solved Problem9-1 showed the synthesis of...Ch. 9.7A - Show how you might synthesize the following...Ch. 9.7B - Prob. 9.8PCh. 9.7B - Show how you would synthesize...Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...
Ch. 9.8 - When 2,2-dibromo-1-phenylpropane is heated...Ch. 9.9C - Show how you would convert a. oct-3-yne to...Ch. 9.9C - The fragrance of (Z)-1-phenylhex-2-en-1-ol...Ch. 9.9D - In the addition of just 1 mole of bromine to 1...Ch. 9.9E - Propose a mechanism for the entire reaction of...Ch. 9.9E - Predict the major product(s) of the following...Ch. 9.9E - Propose a mechanism for the reaction of pent-1-yne...Ch. 9.9E - Show how hex-1-yne might be converted to a....Ch. 9.9F - When pent-2-yne reacts with mercuric sulfate in...Ch. 9.9F - Prob. 9.20PCh. 9.9F - Prob. 9.21PCh. 9.9F - Prob. 9.22PCh. 9.10A - Predict the product(s) you would expect from...Ch. 9.10B - Prob. 9.24PCh. 9.10B - Prob. 9.25PCh. 9 - Prob. 9.26SPCh. 9 - Give common names for the following compounds. a....Ch. 9 - Prob. 9.28SPCh. 9 - Prob. 9.29SPCh. 9 - Using cyclooctyne as your starting material, show...Ch. 9 - Prob. 9.31SPCh. 9 - Prob. 9.32SPCh. 9 - Predict the products of reaction of pent-1-yne...Ch. 9 - Show how you would accomplish the following...Ch. 9 - Show how you would synthesize the following...Ch. 9 - Predict the products formed when CH3CH2C C : Na+...Ch. 9 - Prob. 9.37SPCh. 9 - Prob. 9.38SPCh. 9 - When compound Z is treated with ozone, followed by...Ch. 9 - Show how you would convert the following starting...Ch. 9 - The following functional-group interchange is a...Ch. 9 - Using any necessary inorganic reagents, show how...Ch. 9 - Prob. 9.43SP
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