ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
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Question
Chapter 27, Problem 27.27P
Interpretation Introduction
(a)
Interpretation: The product formed on thermal electrocyclic ring opening of the given compounds is to be predicted.
Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in thermal conditions undergoes reaction in conrotatory fashion and polyene containing odd number of bonds undergo reaction in disrotatory fashion.
Interpretation Introduction
(b)
Interpretation: The product formed on photochemical electrocyclic ring opening of the given compounds.
Concept introduction: Electrocyclic reactions involve ring opening or ring closure in a conjugated polyene. According to Woodward-Hoffmann rules, the polyene containing even number of bonds in photochemical conditions undergoes reaction in disrotatory fashion and polyene containing odd number of bonds undergo reaction in conrotatory fashion.
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(a) What product is formed when each compound undergoes a thermal electrocyclic ring opening? (b) What product is formed when each compound undergoes a photochemical electrocyclic ring opening?
(a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b)What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.
(a) What product is formed when triene N undergoes thermal electrocyclic ring closure? (b) What product is formed when triene N undergoes photochemical ring closure? (c) Label each process as conrotatory or disrotatory.
Chapter 27 Solutions
ORGANIC CHEMISTRY
Ch. 27 - Prob. 27.1PCh. 27 - Problem 27.2
For each molecular orbital in Figure...Ch. 27 - Problem 27.3
(a) Using Figure 27.2 as a guide,...Ch. 27 - Problem 27.4
(a) How many molecular orbitals are...Ch. 27 - Prob. 27.5PCh. 27 - Prob. 27.6PCh. 27 - Prob. 27.7PCh. 27 - Prob. 27.8PCh. 27 - Prob. 27.9PCh. 27 - Prob. 27.10P
Ch. 27 - Problem 27.11
What product would be formed by the...Ch. 27 - Consider cycloheptatrienone and ethylene, and draw...Ch. 27 - Problem 27.13
Show that a thermal suprafacial...Ch. 27 - Prob. 27.14PCh. 27 - a Draw the product of the following [4+2]...Ch. 27 - Prob. 27.16PCh. 27 - Prob. 27.17PCh. 27 - Problem 27.18
Using orbital symmetry, explain why...Ch. 27 - Prob. 27.19PCh. 27 - Prob. 27.20PCh. 27 - Prob. 27.21PCh. 27 - Prob. 27.22PCh. 27 - Prob. 27.23PCh. 27 - Prob. 27.24PCh. 27 - Problem 27.25
(a) What product is formed by the...Ch. 27 - Prob. 27.26PCh. 27 - Prob. 27.27PCh. 27 - Prob. 27.28PCh. 27 - Prob. 27.29PCh. 27 - Prob. 27.30PCh. 27 - Prob. 27.31PCh. 27 - Prob. 27.32PCh. 27 - Prob. 27.33PCh. 27 - Prob. 27.34PCh. 27 - Prob. 27.35PCh. 27 - Prob. 27.36PCh. 27 - Prob. 27.37PCh. 27 - Prob. 27.38PCh. 27 - Prob. 27.39PCh. 27 - Prob. 27.40PCh. 27 - 27.41 What starting materials are needed to...Ch. 27 - Prob. 27.42PCh. 27 - Prob. 27.43PCh. 27 - Prob. 27.44PCh. 27 - Prob. 27.45PCh. 27 - Prob. 27.46PCh. 27 - 27.47 What product is formed from the [5,5]...Ch. 27 - Prob. 27.48PCh. 27 - 27.49 Draw structures for A, B, and C in the...Ch. 27 - Prob. 27.50PCh. 27 - Prob. 27.51PCh. 27 - 27.52 Draw the products of each reaction.
c....Ch. 27 - Prob. 27.53PCh. 27 - 27.54 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.55PCh. 27 - Prob. 27.56PCh. 27 - Prob. 27.57PCh. 27 - 27.58 Draw a stepwise, detailed mechanism for the...Ch. 27 - Prob. 27.59PCh. 27 - Prob. 27.60PCh. 27 - Prob. 27.61PCh. 27 - Prob. 27.62PCh. 27 - Prob. 27.63P
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- For alkenes A, B, C, and D: (a) Rank A—D in order of increasing heat of hydrogenation; (b) rank A—D in order of increasing rate of reaction with H2, Pd-C; (c) draw the products formed when each alkene is treated with ozone, followed by Zn, H2O.arrow_forwardConsider the tetracyclic compound with rings labeled A–D. (a) Which ring is the most reactive in electrophilic aromatic substitution? (b) Which ring is the least reactive in electrophilic aromatic substitution?arrow_forwardWhen (R)-6-bromo-2,6-dimethylnonane is dissolved in CH3OH, nucleophilic substitution yields an optically inactive solution. When the isomeric halide (R)-2-bromo-2,5-dimethylnonane is dissolved in CH3OH under the same conditions, nucleophilic substitution forms an optically active solution. Draw the products formed in each reaction, and explain why the difference in optical activity is observed.arrow_forward
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