Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Question
Chapter 22, Problem 54P
Interpretation Introduction
Interpretation:
The compounds A and B that are isomeric
Concept introduction:
Spectroscopy is a method that is used to identify the structure of the molecule. It is based on the interactions between matter and
Proton NMR spectroscopy identifies the number of hydrogen atoms present in a molecule and the nature of the
The value of chemical peaks depends upon the chemical environment around the hydrogen atom.
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Considering Hinsberg's Method to determine, 1°, 2°, 3° amines.
Draw the structure of the products of the following reactions.
Aniline (1°) + BSC, excess NaOH(DRAW STRUCTURE), then, + HCl (DRAW STRUCTURE)
Diethylamine (2°)+ BSC, excess NaOH (DRAW STRUCTURE), then, + HCl (DRAW STRUCTURE)
Triethylamine (3°)+ BSC, excess NaOH(DRAW STRUCTURE), then, + HCl (DRAW STRUCTURE)
Hinsberg's Method to determine, 1°, 2°, 3° amines.
Draw the structure of the products of the following reactions.
Aniline (1°) + BSC, excess NaOH (DRAW STRUCTURE), then + HCl (DRAW STRUCTURE)
Diethylamine (2°)+ BSC, excess NaOH (DRAW STRUCTURE), then + HCl (DRAW STRUCTURE)
Triethylamine (3°)+ BSC, excess NaOH(DRAW STRUCTURE), then + HCl (DRAW STRUCTURE)
Each hydrogen of a primary amide typically has a separate 1H-NMR resonance, as illustrated by the separate signals for the two amide hydrogens of propanamide, which fall at δ 6.22 and δ 6.58. Furthermore, each methyl group of N,N-dimethylformamide has a separate resonance (δ 3.88 and δ 3.98). How do you account for these observations?
Chapter 22 Solutions
Organic Chemistry - Standalone book
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Prob. 3PCh. 22.2 - Prob. 4PCh. 22.4 - Prob. 5PCh. 22.4 - Prob. 6PCh. 22.4 - Prob. 7PCh. 22.4 - Prob. 8PCh. 22.4 - Prob. 9PCh. 22.7 - Prob. 10P
Ch. 22.8 - Problem 22.11 Three of the following amines can be...Ch. 22.9 - Prob. 12PCh. 22.10 - Prob. 13PCh. 22.13 - Prob. 14PCh. 22.14 - Prob. 15PCh. 22.15 - Prob. 16PCh. 22.15 - Prob. 17PCh. 22.17 - Prob. 18PCh. 22.17 - Prob. 19PCh. 22.17 - Prob. 20PCh. 22.17 - Prob. 21PCh. 22.18 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Arrange the following compounds or anions in each...Ch. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - The compound shown is a somewhat stronger base...Ch. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Write the structure of the product formed on...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - Devise efficient syntheses of each of the...Ch. 22 - Prob. 46PCh. 22 - Prob. 47PCh. 22 - Prob. 48PCh. 22 - Prob. 49PCh. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - Prob. 52PCh. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56DSPCh. 22 - Prob. 57DSPCh. 22 - Prob. 58DSPCh. 22 - Prob. 59DSPCh. 22 - Synthetic Applications of Enamines The formation...Ch. 22 - Prob. 61DSP
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- 34. Pentan-1-amine vs. Pentanamide When comparing pentanal and pentan-3-one: 1. How do the amount of peaks differ? 2. Compare the range of PPM 3. Are there any other differences or similarities? Which carbon would be present at 173 В. NH2 4. С. Е. ppm? Spectra for pentane Spectra for pentanamide 10 20 PPM 35 30 25 15 180 160 120 40 34 100 PPM 140 80 60 20arrow_forwardDraw the structure of the following three isomeric amides with chemical formula C,H NO. Amide #1: N-ethylcyclopropanecarboxamide Amide #2: (Z)-3-hexenamide Amide #3: N-methylcyclobutanecarboxamide • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. opy aste ChemDoodle (Provious Next Email Instructor Save aarrow_forwardPhenacetin, a substance formerly used in over-the-counter headache remedies, has the formula C10H13NO2. Phenacetin is neutral and does not dissolve in either acid or base. When warmed with aqueous NaOH, phenacetin yields an amine, C8H11NO, whose 1H NMR spectrum is shown. When heated with HI, the amine is cleaved to an aminophenol, C6H7NO. What is the structure of phenacetin, and what are the structures of the amine and the aminophenol?arrow_forward
- 4. (Chapter 15 - 472) An aromatic compound C3H;Br has the following H NMR spectrum and a peak at 820 cm in its IR spectrum. Answer the following questions. Chem. Rel. shit area 3.00 2.00 120 2.58 207 2.00 739 2.00 TMS 5 Chemical shift (8) O ppm 10 1 ing 4(a). The IR peak at 820 cm1 in its IR spectrum indicates that the compound is. disubstituted = 4(b) The name of the compound is = Intensityarrow_forwardDetermine the hybridization around the N atom in each amine, andexplain why cyclohexanamine is 106 times more basic than aniline.arrow_forwardExplain the observed difference in the pKa values of the conjugate acids of amines A and B.arrow_forward
- What are the derivate reagents for the following compound: MDMA (N-methyl-N-trifluoroacetyl-3,4-methylenedioxyamphetamine)?arrow_forwardDraw the structure of the following three isomeric amides with chemical formula CGH|NO. Amide #1: N-ethylcyclopropanecarboxamide Amide #2: (Z)-3-hexenamide Amide #3: N-methylcyclobutanecarboxamide • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate structures with + signs from the drop-down menu. P opy aste ChemDoodle®arrow_forwardPropose a structure for an amine with molecular formula C6H7N by interpreting the given "H and 13c NMR data below. 1H NMR Ō 2.35 ppm Ō 7.10 ppm Ō 8.46 ppm singlet (3) doublet (2) doublet (2) 13C NMR 2, 4 1,5 6.00 5.00- 4.00 3.00- 2.00- 1.00- 0.00- 200 180 160 140 120 100 80 60 40 20 8/ ppmarrow_forward
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