EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
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Textbook Question
Chapter 15.5, Problem 15.7P
Propose a mechanism for each reaction, showing explicitly how the observed mixtures of products are formed.
- a. 3 — methylbut — 2 — en — 1 — ol -+- HBr→1 — bromo — 3 — methylbut — 2 — ene + 3 — bromo — 3 — methylbut — 1 — ene
- b. 2 — methylbut — 3 — en — 2 — ol + HBr → 1 — bromo — 3 — methylbut — 2 — ene + 3 — bromo — 3 — methylbut — 1 — ene
- c. cyclopenta-1,3-diene + Br2 →3,4-dibromocyclopent-1-ene + 3,5-dibromocyclopent-1-ene
- d. 1 — chlorobut — 2 — ene + AgNO3, H2O→but — 2 — en — 1 — ol + but — 3 — en — 2 — ol
- e. 3 — chlorobut — 1 — ene + AgNO3, H2O→but — 2 — en — 1 — ol + but — 3 — en — 2 — ol
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3. Consider the compounds below and determine if they are aromatic, antiaromatic, or
non-aromatic. In case of aromatic or anti-aromatic, please indicate number of I
electrons in the respective systems. (Hint: 1. Not all lone pair electrons were explicitly
drawn and you should be able to tell that the bonding electrons and lone pair electrons
should reside in which hybridized atomic orbital 2. You should consider ring strain-
flexibility and steric repulsion that facilitates adoption of aromaticity or avoidance of anti-
aromaticity)
H H
N
N:
NH2
N
Aromaticity
(Circle)
Aromatic Aromatic Aromatic Aromatic Aromatic
Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic
nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic
aromatic TT
electrons
Me
H
Me
Aromaticity
(Circle)
Aromatic Aromatic Aromatic
Aromatic Aromatic
Antiaromatic Antiaromatic Antiaromatic Antiaromatic Antiaromatic
nonaromatic nonaromatic nonaromatic nonaromatic nonaromatic
aromatic πT
electrons
H
HH…
A chemistry graduate student is studying the rate of this reaction:
2 HI (g) →H2(g) +12(g)
She fills a reaction vessel with HI and measures its concentration as the reaction proceeds:
time
(minutes)
[IH]
0
0.800M
1.0
0.301 M
2.0
0.185 M
3.0
0.134M
4.0
0.105 M
Use this data to answer the following questions.
Write the rate law for this reaction.
rate
= 0
Calculate the value of the rate constant k.
k =
Round your answer to 2 significant digits. Also be
sure your answer has the correct unit symbol.
None
Chapter 15 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 15.2 - Prob. 15.1PCh. 15.2 - Prob. 15.2PCh. 15.2 - Prob. 15.3PCh. 15.4 - Prob. 15.4PCh. 15.4 - Prob. 15.5PCh. 15.5 - Treatment of an alkyl halide with AgNO3 in alcohol...Ch. 15.5 - Propose a mechanism for each reaction, showing...Ch. 15.6 - When Br2 is added to buta-1,3-diene at 15 C, the...Ch. 15.7 - Prob. 15.9PCh. 15.7 - When N-bromosuccinimide is added to hex-1-ene in...
Ch. 15.7 - Prob. 15.11PCh. 15.9 - Addition of 1-bromobut-2-ene to magnesium metal in...Ch. 15.10 - Show how you might synthesize the following...Ch. 15.11 - Predict the products of the following proposed...Ch. 15.11 - Prob. 15.15PCh. 15.11A - Prob. 15.16PCh. 15.11B - Prob. 15.17PCh. 15.11B - Predict the products of the following Diels-Alder...Ch. 15.12C - Prob. 15.19PCh. 15.12C - Prob. 15.20PCh. 15.13C - Prob. 15.21PCh. 15.13D - Using the examples in Table15-2 to guide you,...Ch. 15.14 - Phenolphthalein is an acid-base indicator that is...Ch. 15 - Prob. 15.24SPCh. 15 - Prob. 15.25SPCh. 15 - Show how the reaction of an allylic halide with a...Ch. 15 - Prob. 15.27SPCh. 15 - A solution was prepared using 0.0010 g of an...Ch. 15 - Prob. 15.29SPCh. 15 - Prob. 15.30SPCh. 15 - Prob. 15.31SPCh. 15 - Prob. 15.32SPCh. 15 - Prob. 15.33SPCh. 15 - Give the structures of the products represented by...Ch. 15 - Furan and malemide undergo a Diels-Alder reaction...Ch. 15 - Prob. 15.36SPCh. 15 - Prob. 15.37SPCh. 15 - Prob. 15.38SPCh. 15 - Prob. 15.39SPCh. 15 - Determine whether each structure is likely to be...Ch. 15 - An important variation of the Diels-Alder reaction...
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