ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
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Question
Chapter 5, Problem 34P
Interpretation Introduction
Interpretation:
The principal organic products of each reaction are to be determined from the given reagent and organic reactant.
Concept Introduction:
When alcohol treated with hydrogen halide typically undergoes nucleophilic substitution reaction to yield
When three moles of alcohol react with phosphorus tribromide to yield alkyl halide with phosphorous acid and hydrogen bromide.
When alcohols treated with thionyl chlorides in the presence of pyridine react to yield alkyl chloride with sulfur dioxide and hydrogen chloride.
When alcohols treated with methyl sulfonyl chloride react in the presence of pyridine to yield butyl methanesulfonate.
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3. For the reactions below, draw the arrows corresponding to the transformations and draw in the boxes the reactants
or products as indicated. Note: Part A should have arrows drawn going from the reactants to the middle structure
and the arrows on the middle structure that would yield the final structure. For part B, you will need to draw in
the reactant before being able to draw the arrows corresponding to product formation.
A.
B.
Rearrangement
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2. Draw the arrows required to make the following reactions occur. Please ensure your arrows point from exactly
where you want to exactly where you want. If it is unclear from where arrows start or where they end, only partial
credit will be given. Note: You may need to draw in lone pairs before drawing the arrows.
A.
B.
H-Br
人
C
Θ
CI
H
Cl
Θ
+
Br
O
4. For the reactions below, draw the expected product. Be sure to indicate relevant stereochemistry or formal
charges in the product structure.
a)
CI, H
e
b)
H
lux ligh
Br
'H
Chapter 5 Solutions
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
Ch. 5.1 - Prob. 1PCh. 5.1 - Prob. 2PCh. 5.1 - Many compounds contain more than one functional...Ch. 5.2 - Prob. 4PCh. 5.3 - Prob. 5PCh. 5.4 - Classify the isomeric C4H10O alcohols as being...Ch. 5.5 - Bromine is less electronegative than chlorine, yet...Ch. 5.6 - Prob. 8PCh. 5.7 - Prob. 9PCh. 5.8 - Prob. 10P
Ch. 5.8 - Prob. 11PCh. 5.9 - Carbocations are key intermediates in petroleum...Ch. 5.9 - Prob. 13PCh. 5.9 - Prob. 14PCh. 5.11 - Prob. 15PCh. 5.13 - Prob. 16PCh. 5.14 - For the reaction of a primary alcohol RCH2OH with...Ch. 5.15 - Prob. 18PCh. 5 - Write structural formulas for each of the...Ch. 5 - Prob. 20PCh. 5 - Prob. 21PCh. 5 - Write structural formulas for all the...Ch. 5 - Prob. 23PCh. 5 - Prob. 24PCh. 5 - Epichlorohydrin is the common name of an...Ch. 5 - Prob. 26PCh. 5 - Prob. 27PCh. 5 - Prob. 28PCh. 5 - Some of the most important organic compounds in...Ch. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - The reaction of 2,2-dimethyl-1-propanol...Ch. 5 - (a) Assuming that the rate-determining elementary...Ch. 5 - The reaction of 3-tert-butyl-3-pentanol with...Ch. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46DSPCh. 5 - Prob. 47DSPCh. 5 - Prob. 48DSPCh. 5 - Prob. 49DSPCh. 5 - Prob. 50DSPCh. 5 - Prob. 51DSPCh. 5 - Prob. 52DSP
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