Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 3, Problem 13PP
Interpretation Introduction

Interpretation:

The carbon–oxygen bond lengths and the equal negative charge on oxygens of an acetate ion are to be explained by drawing resonance structures.

Concept introduction:

Resonance is the phenomenon of describing delocalized electrons in certain molecular ions through various forms or resonance structures and the forms contributing to the hybrid form.

The positions of electrons are different, without effecting the positions of the nuclei.

The effect of delocalization is caused by resonance, where the negative charge is distributed among the oxygen atoms in a carboxylate ion.

The rules for drawing resonance structures are as follows:

Only nonbonding electron pairs and pi electrons can participate in conjugation in the formation of various resonating structures.

The single bonds present in the molecule do not break or form in the resonance structures.

The placement of atoms present in the molecule remains fixed.

The octet of all atoms is completely filled.

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Draw all resonance contributors for each of the following molecules or ions. Be sure to include the curved arrows thatindicate which pairs of electrons are shifted in going from one resonance structure to the next.(a) CH3NO2(b) CH3CO-2(c) CH3CHCHCH-2(the ion has two C-C single bonds)(d) C5H5N (a ring is formed by the C and N atoms, and each H is bonded to C)(e) C4H5N (a ring is formed by the C and N atoms, the N is bonded to one H, and each C is bonded to one H)
Consider Lewis formulas A, B, and C:(a) Are A, B, and C constitutional isomers, or are they resonance contributors? (b) Which have a negatively charged carbon? (c) Which have a positively charged carbon? (d) Which have a positively charged nitrogen? (e) Which have a negatively charged nitrogen? (f) What is the net charge on each? (g) Which is a more stable structure, A or B? Why? (h) Which is a more stable structure, B or C? Why? (i) What is the CNN geometry in each according to VSEPR?
2. On the first drawing on the left for each structure below, draw the electron pushing arrows needed to produce the resonance structure on the right. The structures are bond-line; you need to draw the implied lone pair electrons that participate in resonance. (b) (a) Ⓒ

Chapter 3 Solutions

Organic Chemistry

Ch. 3 - Prob. 11PPCh. 3 - Prob. 12PPCh. 3 - Prob. 13PPCh. 3 - Prob. 14PPCh. 3 - PRACTICE PROBLEM 3.15 Nitro groups have a large...Ch. 3 - PRACTICE PROBLEM 3.16 Your laboratory instructor...Ch. 3 - Prob. 17PPCh. 3 - Prob. 18PPCh. 3 - Prob. 19PPCh. 3 - What is the conjugate base of each of the...Ch. 3 - List the bases you gave as answers to Problem 3.20...Ch. 3 - 3.22 What is the conjugate acid of each of the...Ch. 3 - List the acids you gave as answers to Problem 3.22...Ch. 3 - Rank the following in order of increasing acidity.Ch. 3 - Without consulting tables, select the stronger...Ch. 3 - Designate the Lewis acid and Lewis base in each of...Ch. 3 - Prob. 27PCh. 3 - Prob. 28PCh. 3 - Write an equation, using the curved-arrow...Ch. 3 - 3.30 What reaction will take place if ethyl...Ch. 3 - 3.31 (a) The of formic acid. What is the? (b)...Ch. 3 - Acid HA has pKa=20; acid HB has pKa=10. (a) Which...Ch. 3 - Prob. 33PCh. 3 - 3.34 (a) Arrange the following compounds in order...Ch. 3 - 3.35 Arrange the following compounds in order of...Ch. 3 - 3.36 Arrange the following in order of increasing...Ch. 3 - Prob. 37PCh. 3 - 3.38 Supply the curved arrows necessary for the...Ch. 3 - Glycine is an amino acid that can be obtained from...Ch. 3 - 3.40 Malonic acid, , is a diprotic acid. The for...Ch. 3 - 3.41 The free-energy change, , for the ionization...Ch. 3 - 3.42 At the enthalpy change, , for the ionization...Ch. 3 - The compound at right has (for obvious reasons)...Ch. 3 - 3.44. (a) Given the above sequence of...Ch. 3 - Prob. 45PCh. 3 - Prob. 46PCh. 3 - 3.47 As noted in Table 3.1, the of acetone, , is...Ch. 3 - Formamide (HCONH2) has a pKa of approximately 25....Ch. 3 - List all the chemical species likely to be present...Ch. 3 - Prob. 2LGPCh. 3 - Prob. 3LGPCh. 3 - Prob. 4LGP
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