Organic Chemistry: Structure and Function
8th Edition
ISBN: 9781319079451
Author: K. Peter C. Vollhardt, Neil E. Schore
Publisher: W. H. Freeman
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Chapter 7, Problem 69P
Interpretation Introduction
Interpretation: The most stable carbocation needs to be determined.
Concept introduction: Carbocations are intermediates form during a reaction and their stability depends on three main factors listed below:
- The stability of carbocations increases with an increase in the number of carbon atoms in the molecule. (tertiary carbocation > secondary carbocation > primarycarbocation).
- Presence of pi bonds which allow carbocation to take part in resonance which stabilizes the positive charge on carbocation.
- Presence of electron donating group or atom with lone pairs.
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When an unknown amine reacts with an unknown acid chloride, an amide with a molecular mass of 163 g/mol (M* = 163 m/z)
is formed. In the infrared spectrum, important absorptions appear at 1661, 750 and 690 cm. The 13C NMR and DEPT spectra
are provided. Draw the structure of the product as the resonance contributor lacking any formal charges.
13C NMR
DEPT 90
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DEPT 135
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Draw the unknown amide.
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Chapter 7 Solutions
Organic Chemistry: Structure and Function
Ch. 7.1 - Prob. 7.1ECh. 7.2 - Prob. 7.2ECh. 7.3 - Prob. 7.3ECh. 7.3 - Prob. 7.5TIYCh. 7.4 - Prob. 7.7TIYCh. 7.5 - Prob. 7.9TIYCh. 7.6 - Prob. 7.10ECh. 7.7 - Prob. 7.11ECh. 7.7 - Prob. 7.12ECh. 7.7 - Prob. 7.13E
Ch. 7.7 - Prob. 7.15TIYCh. 7.8 - Prob. 7.16ECh. 7.8 - Prob. 7.17ECh. 7.9 - Prob. 7.18ECh. 7.9 - Prob. 7.19ECh. 7.9 - Prob. 7.20ECh. 7.9 - Prob. 7.21ECh. 7.9 - Prob. 7.22ECh. 7 - Prob. 25PCh. 7 - Prob. 26PCh. 7 - Prob. 27PCh. 7 - Prob. 28PCh. 7 - Prob. 29PCh. 7 - Prob. 30PCh. 7 - Prob. 31PCh. 7 - Prob. 32PCh. 7 - Prob. 33PCh. 7 - Prob. 34PCh. 7 - Prob. 35PCh. 7 - Prob. 36PCh. 7 - Prob. 37PCh. 7 - Prob. 38PCh. 7 - Prob. 39PCh. 7 - Prob. 40PCh. 7 - Prob. 41PCh. 7 - Prob. 42PCh. 7 - Prob. 43PCh. 7 - Prob. 44PCh. 7 - Prob. 45PCh. 7 - Prob. 46PCh. 7 - Prob. 47PCh. 7 - Prob. 48PCh. 7 - Prob. 49PCh. 7 - Prob. 50PCh. 7 - Prob. 51PCh. 7 - Prob. 52PCh. 7 - Prob. 53PCh. 7 - Prob. 54PCh. 7 - Prob. 55PCh. 7 - Prob. 56PCh. 7 - Prob. 57PCh. 7 - Prob. 58PCh. 7 - Prob. 59PCh. 7 - Prob. 60PCh. 7 - Prob. 61PCh. 7 - Prob. 62PCh. 7 - Prob. 63PCh. 7 - Prob. 64PCh. 7 - Prob. 65PCh. 7 - Prob. 66PCh. 7 - Prob. 67PCh. 7 - Prob. 68PCh. 7 - Prob. 69PCh. 7 - Prob. 70P
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