ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
ORGANIC CHEMISTRY (LL)-W/SOLN.>CUSTOM<
10th Edition
ISBN: 9781259972348
Author: Carey
Publisher: MCG CUSTOM
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Chapter 9, Problem 27P
Interpretation Introduction

Interpretation:

The principal product in each of the given reactions is to be predicted.

Concept introduction:

The conjugate base of alkyne acts as a good nucleophile. On reaction with primary alkyl halide, it undergoes substitution reaction. The order of better leaving group of halogen in a nucleophilic substitution reaction is I>Br>Cl>F.

Alkynes, on hydrogenation with catalyst Lindlar palladium, undergo syn addition and yield cis alkene.

Alkynes, on hydration, undergo addition of a molecule of water. The hydrogen atom is bonded to less substituted triple bonded carbon, and the hydroxyl groupis bonded to more substituted triple bonded carbon atom and forms a ketone through enol formation.

Germinal and vicinal dihalides, on reaction with a strong base, undergo double dehydrohalogenation and form alkynes.

Ozonolysis of alkynes involves the cleavage of triple bond and formation of carboxylic acids as products. An acyclic alkyne forms two carboxylic acids whereas a cyclic alkyne forms a single product with two carboxylic acid groups.

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Done 11:14 ⚫ worksheets.beyondlabz.com 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 9 Solutions

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