Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 10.6C, Problem 10.9P
A nitro group (—NO2) effectively stabilizes a negative charge on an adjacent carbon atom through resonance:
Two of the following nitrophenols are much more acidic than phenol itself. The third compound is only slightly more acidic than phenol. Use resonance structures of the appropriate phenoxide ions to show why two of these anions should be unusually stable.
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22.22 For each compound, indicate which group on the ring is more strongly activating and then
draw a structural formula of the major product formed by nitration of the compound.
Br
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OCHS
NO₂
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CO₂H
NHCOCH3
NHCOCH,
(h)
CHS
22.23 The following molecules each contain two aromatic rings.
(b)
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(c)
Which ring in each undergoes electrophilic aromatic substitution more readily? Draw
the major product formed on nitration.
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Chapter 10 Solutions
Organic Chemistry (9th Edition)
Ch. 10.3A - Prob. 10.1PCh. 10.3B - Give both the IUPAC name and the common name for...Ch. 10.3B - Prob. 10.3PCh. 10.3C - Give a systematic (IUPAC) name for each diol. a....Ch. 10.4B - Predict which member of each pair will be more...Ch. 10.4B - Dimethylamine (CH3)2NH, has a molecular weight of...Ch. 10.6A - Prob. 10.7PCh. 10.6A - Prob. 10.8PCh. 10.6C - A nitro group (NO2) effectively stabilizes a...Ch. 10.6C - Prob. 10.10P
Ch. 10.8B - Prob. 10.11PCh. 10.8B - Prob. 10.12PCh. 10.9A - Prob. 10.13PCh. 10.9B - Prob. 10.14PCh. 10.9C - Show how you would synthesize each tertiary...Ch. 10.9D - Prob. 10.16PCh. 10.9D - Show how you would add Grignard reagents to acid...Ch. 10.9D - A formate ester, such as ethyl formate, reacts...Ch. 10.9E - Prob. 10.19PCh. 10.9E - In Section9-7B, we saw how acetylide ions add to...Ch. 10.9F - Prob. 10.21PCh. 10.10A - Prob. 10.22PCh. 10.10B - Prob. 10.23PCh. 10.11B - Predict the products you would expect from the...Ch. 10.11B - Prob. 10.25PCh. 10.11B - Prob. 10.26PCh. 10.12 - Prob. 10.27PCh. 10.12 - Prob. 10.28PCh. 10.12 - Authentic skunk spray has become valuable for use...Ch. 10 - Give a systematic (IUPAC) name for each alcohol....Ch. 10 - Give systematic (IUPAC) names for the following...Ch. 10 - Draw the structures of the following compounds...Ch. 10 - Predict which member of each pair has the higher...Ch. 10 - Predict which member of each pair is more acidic,...Ch. 10 - Predict which member of each group is most soluble...Ch. 10 - Draw the organic products you would expect to...Ch. 10 - Prob. 10.37SPCh. 10 - Show how you would synthesize the following...Ch. 10 - Show how you would use Grignard syntheses to...Ch. 10 - Show how you would accomplish the following...Ch. 10 - Show how you would synthesize the following: a....Ch. 10 - Complete the following acid-base reactions. In...Ch. 10 - Prob. 10.43SPCh. 10 - Prob. 10.44SPCh. 10 - Geminal diols, or 1,1-diols, are usually unstable,...Ch. 10 - Vinyl alcohols are generally unstable, quickly...Ch. 10 - Compound A (C7H11Br) is treated with magnesium in...Ch. 10 - Prob. 10.48SPCh. 10 - Prob. 10.49SPCh. 10 - Prob. 10.50SPCh. 10 - Prob. 10.51SPCh. 10 - Prob. 10.52SPCh. 10 - Prob. 10.53SPCh. 10 - Prob. 10.54SPCh. 10 - Prob. 10.55SPCh. 10 - Prob. 10.56SPCh. 10 - Show how this 1 alcohol can be made from the...Ch. 10 - Prob. 10.58SPCh. 10 - Prob. 10.59SPCh. 10 - Prob. 10.60SP
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