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 2, Problem 28PP
Interpretation Introduction

Interpretation:

Based on the resonance and the electronegativity effects, the trends in carbonyl IR stretching frequencies from higher frequency for esters and carboxylic acids to lower frequency for amides are to be explained. Also, the way the nitrogen atom influences the distribution of electrons in an amide carbonyl group is to be suggested.

Concept Introduction:

▸ Infrared spectroscopy is a simple, instrumental technique, which helps to determine the presence of various functional groups.

▸ It depends on the interactions of atoms or molecules with the electromagnetic radiation.

▸ The molecules which have dipole moment are IR active and the molecules which do not have dipole moment are IR inactive.

▸ The change in the absorption frequency of a particular group takes place by changing the substituents in the neighborhood of that particular group.

▸ An electronegative atom or group causes –-I effect, which results in the bond order to increase.

▸ The lengthening and weakening of a bond leads to lower absorption frequency.

▸ The double bond character of carbonyl increases as the electronegativity of the atom bonded to carbonyl group increases.

▸ In amides the electron pair of nitrogen atom contributes to the resonance hybrid which decreases the double bond character.

▸ In case of carboxylic acid and esters, the carbonyl group is attached to the electronegative oxygen atom, which results in the increase of carbonyl absorption frequency.

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Chapter 2 Solutions

Organic Chemistry

Ch. 2 - Practice Problem 2.11 Although we shall discuss...Ch. 2 - Practice Problem 2.12 Write bond-line structural...Ch. 2 - Prob. 13PPCh. 2 - Practice Problem 2.14 One way of naming ethers is...Ch. 2 - Practice Problem 2.15 Eugenol is the main...Ch. 2 - Practice Problem 2.16 One way of naming amines is...Ch. 2 - Practice Problem 2.17 Which amines in Practice...Ch. 2 - Prob. 18PPCh. 2 - Prob. 19PPCh. 2 - Practice Problem 2.20 Write bond-line formulas for...Ch. 2 - Practice Problem 2.21 Write bond-line formulas for...Ch. 2 - Practice Problem 2.22 Write bond-line formulas for...Ch. 2 - Prob. 23PPCh. 2 - Practice Problem 2.24 Write another resonance...Ch. 2 - Prob. 25PPCh. 2 - Practice Problem 2.26 Which compound would you...Ch. 2 - Practice Problem 2.27 Arrange the following...Ch. 2 - Prob. 28PPCh. 2 - Prob. 29PCh. 2 - Identify all of the functional groups in each of...Ch. 2 - 2.31 There are four alkyl bromides with the...Ch. 2 - Prob. 32PCh. 2 - Classify the following alcohols as primary,...Ch. 2 - 2.34 Classify the following amines as primary,...Ch. 2 - Prob. 35PCh. 2 - Identify all of the functional groups in Crixivan,...Ch. 2 - 2.37 Identify all of the functional groups in...Ch. 2 - 2.38 (a) Indicate the hydrophobic and hydrophilic...Ch. 2 - Hydrogen fluoride has a dipole moment of 1.83 D;...Ch. 2 - 2.40 Why does one expect the cis isomer of an...Ch. 2 - Prob. 41PCh. 2 - Prob. 42PCh. 2 - Prob. 43PCh. 2 - 2.44 Consider each of the following molecules in...Ch. 2 - True or false: For a molecule to be polar, the...Ch. 2 - 2.46 Which compound in each of the following...Ch. 2 - Prob. 47PCh. 2 - The IR spectrum of propanoic acid (Fig. 2.16)...Ch. 2 - Prob. 49PCh. 2 - Write structural formulas for four compounds with...Ch. 2 - There are four amides with the formula C3H7NO. (a)...Ch. 2 - Prob. 52PCh. 2 - Prob. 53PCh. 2 - Prob. 54PCh. 2 - Prob. 55PCh. 2 - 2.56 Compound C is asymmetric, has molecular...Ch. 2 - 2.57 Examine the diagram showing an -helical...Ch. 2 - Prob. 1LGPCh. 2 - Prob. 2LGPCh. 2 - Prob. 3LGPCh. 2 - Consider the molecular formula C4H8O2. Predict...Ch. 2 - Consider the molecular formula C4H8O2. If any of...Ch. 2 - Prob. 6LGPCh. 2 - Consider the molecular formula. 7. Pick five...Ch. 2 - Prob. 8LGP
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