ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
10th Edition
ISBN: 9781260008562
Author: Carey
Publisher: MCG
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Chapter 5, Problem 37P
Interpretation Introduction
Interpretation:
An alcohol from given alcohols, which is converted to the corresponding chloride at the fastest rate, on reaction with concentrated hydrochloric acid is to be determined. Which one reacts at the slowest rate is to be determined as well.
Concept Introduction:
The
When a tertiary alcohol reacts with hydrogen chloride, a tertiary carbocation is formed.
When a secondary alcohol reacts with hydrogen chloride, a secondary carbocation is formed.
When a primary alcohol reacts with hydrogen chloride, a primary carbocation is formed.
Tertiary alcohols react fastest while primary alcohols react the slowest on reaction with concentrated hydrochloric acid.
More stable carbocations are formed faster, than less stable carbocations. Thus, tertiary carbocations react the fastest, while primary carbocations react the slowest on reaction with concentrated hydrochloric acid.
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5 (a). Using the peak information you listed in the tables for
both structures, assign each peak to that portion of the
structure that produces the peak in the NMR spectrum. Draw
this diagram on your own sheet of paper and attach the sketch
of your drawing to this question.
Question 6
5 (b). Using the peak information you listed in the tables for
both structures, assign each peak to that portion of the
structure that produces the peak in the NMR spectrum. Draw
this diagram on your own sheet of paper and attach the sketch
of your drawing to this question.
Question 7
6. Are there any differences between the spectra you obtained
in Beyond Labz and the predicted spectra? If so, what were
the differences?
<
2. Predict the NMR spectra for each of these two
compounds by listing, in the NMR tables below, the
chemical shift, the splitting, and the number of
hydrogens associated with each predicted peak. Sort the
peaks from largest chemical shift to lowest.
**Not all slots must be filled**
Peak
Chemical Shift (d)
5.7
1
Multiplicity
multiplate
..........
5.04
double of doublet
2
4.98
double of doublet
3
4.05
doublet of quartet
4
5
LO
3.80
quartet
1.3
doublet
6
Peak
Chemical Shift (d)
Multiplicity
Chapter 5 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)-PACKAGE
Ch. 5.1 - Prob. 1PCh. 5.1 - Prob. 2PCh. 5.1 - Many compounds contain more than one functional...Ch. 5.2 - Prob. 4PCh. 5.3 - Prob. 5PCh. 5.4 - Classify the isomeric C4H10O alcohols as being...Ch. 5.5 - Bromine is less electronegative than chlorine, yet...Ch. 5.6 - Prob. 8PCh. 5.7 - Prob. 9PCh. 5.8 - Prob. 10P
Ch. 5.8 - Prob. 11PCh. 5.9 - Carbocations are key intermediates in petroleum...Ch. 5.9 - Prob. 13PCh. 5.9 - Prob. 14PCh. 5.11 - Prob. 15PCh. 5.13 - Prob. 16PCh. 5.14 - For the reaction of a primary alcohol RCH2OH with...Ch. 5.15 - Prob. 18PCh. 5 - Write structural formulas for each of the...Ch. 5 - Prob. 20PCh. 5 - Prob. 21PCh. 5 - Write structural formulas for all the...Ch. 5 - Prob. 23PCh. 5 - Prob. 24PCh. 5 - Epichlorohydrin is the common name of an...Ch. 5 - Prob. 26PCh. 5 - Prob. 27PCh. 5 - Prob. 28PCh. 5 - Some of the most important organic compounds in...Ch. 5 - Prob. 30PCh. 5 - Prob. 31PCh. 5 - Prob. 32PCh. 5 - Prob. 33PCh. 5 - Prob. 34PCh. 5 - Prob. 35PCh. 5 - Prob. 36PCh. 5 - Prob. 37PCh. 5 - Prob. 38PCh. 5 - Prob. 39PCh. 5 - Prob. 40PCh. 5 - The reaction of 2,2-dimethyl-1-propanol...Ch. 5 - (a) Assuming that the rate-determining elementary...Ch. 5 - The reaction of 3-tert-butyl-3-pentanol with...Ch. 5 - Prob. 44PCh. 5 - Prob. 45PCh. 5 - Prob. 46DSPCh. 5 - Prob. 47DSPCh. 5 - Prob. 48DSPCh. 5 - Prob. 49DSPCh. 5 - Prob. 50DSPCh. 5 - Prob. 51DSPCh. 5 - Prob. 52DSP
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