Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 7, Problem 7.49AP
Interpretation Introduction
Interpretation:
The optically active compounds which on hydrogenation give optically inactive compound are to be predicted.
Concept introduction:
Nucleophilic addition reaction is a type of organic reaction in which the nucleophile is added to the electrophilic site. The carbon atom in carbonyl compound acts as an electrophilic center where a nucleophile attacks and gives an addition product.
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The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown. (a) Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole. (b) Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline. (c) Explain whyelectrophilic substitution occurs more readily at C3 rather than C2 of indole.
Compound F may be synthesised by the method below
Compound A
Compound F
HCI
CH3OH
H₂SO4
Compound B
CH3 CH₂ CH₂
CI
Compound E
NaOH
K₂Cr₂O7
H₂SO4
Compound C
K₂Cr₂O7
H₂SO4
Compound D
Draw the structural formulas of compounds A, C, D, E and F in the boxes provided above.
The bicyclic heterocycles quinoline and indole undergo electrophilic aromatic substitution to give the products shown. (a) Explain why electrophilic substitution occurs on the ring without the N atom for quinoline, but occurs on the ring with the N atom in indole. (b) Explain why electrophilic substitution occurs more readily at C8 than C7 in quinoline. (c) Explain why electrophilic substitution occurs more readily at C3 rather than C2 of indole.
Chapter 7 Solutions
Organic Chemistry
Ch. 7 - Prob. 7.1PCh. 7 - Prob. 7.2PCh. 7 - Prob. 7.3PCh. 7 - Prob. 7.4PCh. 7 - Prob. 7.5PCh. 7 - Prob. 7.6PCh. 7 - Prob. 7.7PCh. 7 - Prob. 7.8PCh. 7 - Prob. 7.9PCh. 7 - Prob. 7.10P
Ch. 7 - Prob. 7.11PCh. 7 - Prob. 7.12PCh. 7 - Prob. 7.13PCh. 7 - Prob. 7.14PCh. 7 - Prob. 7.15PCh. 7 - Prob. 7.16PCh. 7 - Prob. 7.17PCh. 7 - Prob. 7.18PCh. 7 - Prob. 7.19PCh. 7 - Prob. 7.20PCh. 7 - Prob. 7.21PCh. 7 - Prob. 7.22PCh. 7 - Prob. 7.23PCh. 7 - Prob. 7.24PCh. 7 - Prob. 7.25PCh. 7 - Prob. 7.26PCh. 7 - Prob. 7.27PCh. 7 - Prob. 7.28PCh. 7 - Prob. 7.29PCh. 7 - Prob. 7.30PCh. 7 - Prob. 7.31PCh. 7 - Prob. 7.32PCh. 7 - Prob. 7.33PCh. 7 - Prob. 7.34APCh. 7 - Prob. 7.35APCh. 7 - Prob. 7.36APCh. 7 - Prob. 7.37APCh. 7 - Prob. 7.38APCh. 7 - Prob. 7.39APCh. 7 - Prob. 7.40APCh. 7 - Prob. 7.41APCh. 7 - Prob. 7.42APCh. 7 - Prob. 7.43APCh. 7 - Prob. 7.44APCh. 7 - Prob. 7.45APCh. 7 - Prob. 7.46APCh. 7 - Prob. 7.47APCh. 7 - Prob. 7.48APCh. 7 - Prob. 7.49APCh. 7 - Prob. 7.50APCh. 7 - Prob. 7.51APCh. 7 - Prob. 7.52APCh. 7 - Prob. 7.53APCh. 7 - Prob. 7.54APCh. 7 - Prob. 7.55APCh. 7 - Prob. 7.56APCh. 7 - Prob. 7.57APCh. 7 - Prob. 7.58APCh. 7 - Prob. 7.59APCh. 7 - Prob. 7.60APCh. 7 - Prob. 7.61APCh. 7 - Prob. 7.62APCh. 7 - Prob. 7.63APCh. 7 - Prob. 7.64APCh. 7 - Prob. 7.65APCh. 7 - Prob. 7.66APCh. 7 - Prob. 7.67APCh. 7 - Prob. 7.68APCh. 7 - Prob. 7.69APCh. 7 - Prob. 7.70APCh. 7 - Prob. 7.71APCh. 7 - Prob. 7.72APCh. 7 - Prob. 7.73APCh. 7 - Prob. 7.74APCh. 7 - Prob. 7.75AP
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