Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 14, Problem 4PP
Practice Problem 14.4
Apply the polygon-and-circle method to the cyclopentadienyl cation and explain whether it would be aromatic or not.
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Practice Problem 13.37a
Draw the major organic product of the following reaction sequence.
1) RCO3H
2) MeMgBr
3) H20
8. (a) Benzene derivatives exhibit medium to
strong absorption in UV-region. Explain
why aniline and phenoxide ion have
strong UV-absorptions.
Practice Problem 13.37c
Draw the major organic product of the following reaction sequence.
1) RCO3H
2) NaSMe
3) H20
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - PRACTICE PROBLEM 14.1 Provide a name for each of...Ch. 14 - Prob. 2PPCh. 14 - Prob. 3PPCh. 14 - Practice Problem 14.4 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.5 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.6 1,3,5-Cycloheptatriene is...Ch. 14 - Prob. 7PPCh. 14 - Prob. 8PPCh. 14 - Practice Problem 14.9 In 1967 R. Breslow (of...Ch. 14 - Prob. 10PP
Ch. 14 - Practice Problem 14.11 In addition to a signal...Ch. 14 - PRACTICE PROBLEM 14.12
Azulene has an appreciable...Ch. 14 - Practice Problem 14.13 (a) The -Sh group is...Ch. 14 - Practice Problem 14.14
Explain how NMR...Ch. 14 - PRACTICE PROBLEM 14.15 Four benzenoid compounds,...Ch. 14 - Prob. 16PCh. 14 - Write structural formulas and give acceptable...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Which of the hydrogen atoms shown below is more...Ch. 14 - 14.22 The rings below are joined by a double bond...Ch. 14 - Prob. 23PCh. 14 - 14.24 (a) In 1960 T. Katz (Columbia University)...Ch. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - 14.27 5-Chloro-1,3-cyclopentadiene (below)...Ch. 14 - Prob. 28PCh. 14 - Furan possesses less aromatic character than...Ch. 14 - 14.30 For each of the pairs below, predict...Ch. 14 - Assign structures to each of the compounds A, B,...Ch. 14 - Prob. 32PCh. 14 - Give a structure for compound F that is consistent...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 37PCh. 14 - Prob. 38PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 41PCh. 14 - Compound E has the spectral features given below....Ch. 14 - Draw all of the molecular orbitals for...Ch. 14 - Prob. 1LGPCh. 14 - Prob. 2LGPCh. 14 - 3. The NMR signals for the aromatic hydrogens of...Ch. 14 - Prob. 4LGPCh. 14 - Prob. 5LGP
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- PRACTICE PROBLEM 8.20 Specify the alkene and reagents needed to synthesize each of the following diols. OH HO- (a) (b) (c) HO. н он HO (racemic) (racemic)arrow_forwardPractice Problem 13.37f Draw the major organic product of the following reaction sequence. .CI 1) Mg, diethyl ether 2) 3) H20arrow_forwardWrite structural formulas for the cyclohexadienyl cations formed from aniline (C6H5NH2) during(a) Ortho bromination (four resonance structures)(b) Meta bromination (three resonance structures)(c) Para bromination (four resonance structures)arrow_forward
- Explain the following observations :(i) The boiling point of ethanol is higher than that of methoxymethane.(ii) Phenol is more acidic than ethanol.(iii) o- and p-nitrophenols are more acidic than phenol.arrow_forwardPractice Problem 16.42 Choose the correct product for the following Diels-Alder reaction. X Your answer is incorrect. Try again. HOOC COOHarrow_forwardPractice Problem 18.39 Rank the following compounds in order of increasing reactivity toward electrophilic aromatic substitution. Br A B Br Br E Increasing reactivity toward electrophilic aromatic substitutionarrow_forward
- (a) CH3CHDOH (b) Show how to make these deuterium-labeled compounds, using CD3MgBr and D2O as your sources of deuterium, and any non-deuterated starting materials you wish. (a) CH3CH(OD)CD3 (d) Ph(CD3)2COD (b) CH3C(OH)(CD3)2 (c) CD3CH2CH2OHarrow_forwardPractice Problem 12.42b Predict the product and draw a mechanism for the following reaction: NABH, MEOH 12.42b Draw the major organic product.arrow_forwardPractice Problem 13.38e Propose a plausible mechanism for the following transformation. NaH CIarrow_forward
- Explain how pyrrole is isoelectronic with the cyclopentadienyl anionarrow_forwardAromaticity On the basis of Huckel's rule, label the following molecules as aromatic, nonaromatic or antiaromatic. Share your answers and comment on two other students' postings - have they correctly labeled the molecules? (a) (c) (e) anthracene [12]annulene azulene (b) (d) [10]annulene [14]annulene S-indacenearrow_forward(c) Diels-Alder reactions are a highly effective way to synthesise stereospecifically fused cyclic structures. (1) Using suitable diagrams, curly arrows and/or reaction schemes, explain why the reaction between cyclopentadiene and maleic anhydride favours formation of the endo product. (ii) If the reaction in part (i) were conducted using furan instead of cyclopentadiene, what difference would you observe in the product/s, with respect to their stereochemistry? (No need to draw reaction mechanisms) (iii) Draw the stereospecific 3D structure of the product formed during the Diels-Alder reaction below. (No need to show the reaction mechanism) Нeat Br Br (Figure Q11ciii)arrow_forward
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