Organic Chemistry, Binder Ready Version
2nd Edition
ISBN: 9781118454312
Author: David R. Klein
Publisher: WILEY
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Question
Chapter 18.6, Problem 4LTS
Interpretation Introduction
Interpretation: For the given transformation an efficient synthesis should be proposed.
Concept introduction:
- When approaching a synthesis problem two questions should be asked
-
- 1. Is there a change in the carbon skeleton?
- 2. Is there a change in the position or identity of the
functional group
- When approaching a synthesis problem, should not encounter a one-step method
- The desired transformation can achieve in two steps
- There are two ways to introduce functionality at a benzylic position
-
- 1. Oxidation, which produces benzoic acid at benzylic position
- 2. Radical bromination, which produces benzylic halide.
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Instructions: Complete the questions in the space provided. Show all your work
1. You are trying to determine the rate law expression for a reaction that you are completing at 25°C. You measure
the initial reaction rate and the starting concentrations of the reactions for 4 trials.
BrO³¯ (aq) + 5Br¯ (aq) + 6H* (aq) → 3Br₂ (l) + 3H2O (l)
Initial rate
Trial
[BrO3]
[H*]
[Br]
(mol/L)
(mol/L) | (mol/L)
(mol/L.s)
1
0.10
0.10
0.10
8.0
2
0.20
0.10
0.10
16
3
0.10
0.20
0.10
16
4
0.10
0.10
0.20
32
a.
Based on the above data what is the rate law expression?
b. Solve for the value of k (make sure to include proper units)
2. The proposed reaction mechanism is as follows:
i.
ii.
BrО¸¯ (aq) + H+ (aq) → HBrO3 (aq)
HBrO³ (aq) + H* (aq) → H₂BrO3* (aq)
iii.
H₂BrO³* (aq) + Br¯ (aq) → Br₂O₂ (aq) + H2O (l)
[Fast]
[Medium]
[Slow]
iv.
Br₂O₂ (aq) + 4H*(aq) + 4Br(aq) → 3Br₂ (l) + H2O (l)
[Fast]
Evaluate the validity of this proposed reaction. Justify your answer.
е.
Д
CH3
D*, D20
C.
NaOMe,
Br
Br
Chapter 18 Solutions
Organic Chemistry, Binder Ready Version
Ch. 18.2 - Prob. 1LTSCh. 18.2 - Prob. 1PTSCh. 18.2 - Prob. 2ATSCh. 18.2 - Prob. 3ATSCh. 18.2 - Prob. 4ATSCh. 18.2 - Prob. 5ATSCh. 18.4 - Prob. 6CCCh. 18.4 - Prob. 8CCCh. 18.4 - Prob. 9CCCh. 18.5 - Prob. 10CC
Ch. 18.5 - Prob. 2LTSCh. 18.5 - Prob. 11PTSCh. 18.5 - Prob. 12ATSCh. 18.5 - Prob. 13ATSCh. 18.5 - Prob. 14ATSCh. 18.5 - Prob. 3LTSCh. 18.5 - Prob. 15PTSCh. 18.5 - Prob. 16ATSCh. 18.5 - Prob. 17ATSCh. 18.5 - Prob. 18CCCh. 18.6 - Prob. 19CCCh. 18.6 - Prob. 4LTSCh. 18.6 - Prob. 20PTSCh. 18.6 - Prob. 21ATSCh. 18.6 - Prob. 22ATSCh. 18.6 - Prob. 23ATSCh. 18.7 - Prob. 5LTSCh. 18.7 - Prob. 24PTSCh. 18.7 - Prob. 25ATSCh. 18.8 - Prob. 26CCCh. 18.8 - Prob. 27CCCh. 18 - Prob. 28PPCh. 18 - Prob. 29PPCh. 18 - Prob. 30PPCh. 18 - Prob. 31PPCh. 18 - Prob. 32PPCh. 18 - Prob. 33PPCh. 18 - Prob. 34PPCh. 18 - Prob. 35PPCh. 18 - Prob. 36PPCh. 18 - Prob. 37PPCh. 18 - Prob. 38PPCh. 18 - Prob. 39PPCh. 18 - Prob. 40PPCh. 18 - Prob. 41PPCh. 18 - Prob. 42PPCh. 18 - Prob. 43PPCh. 18 - Prob. 44PPCh. 18 - Prob. 45PPCh. 18 - Prob. 46PPCh. 18 - Prob. 47PPCh. 18 - Prob. 48PPCh. 18 - Prob. 49PPCh. 18 - Prob. 50PPCh. 18 - Prob. 51PPCh. 18 - Prob. 52PPCh. 18 - Prob. 53IPCh. 18 - Prob. 54IPCh. 18 - Prob. 55IPCh. 18 - Prob. 56IPCh. 18 - Prob. 57IPCh. 18 - Prob. 58IPCh. 18 - Prob. 59IPCh. 18 - Prob. 60IPCh. 18 - Prob. 61IPCh. 18 - Prob. 62IPCh. 18 - Prob. 63IPCh. 18 - Prob. 64IPCh. 18 - Prob. 65IPCh. 18 - Prob. 66IPCh. 18 - Prob. 67IP
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