EBK ORGANIC CHEMISTRY-PRINT COMPANION (
4th Edition
ISBN: 9781119776741
Author: Klein
Publisher: WILEY CONS
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Identify products A and B from the given 1H NMR data.a. Treatment of CH2 = CHCOCH3 with one equivalent of HCl forms compound A. A exhibits the following absorptions in its 1H NMR spectrum: 2.2 (singlet, 3 H), 3.05 (triplet, 2 H), and 3.6 (triplet, 2 H) ppm. What is the structure of A?b. Treatment of acetone [(CH3)2C = O] with dilute aqueous base forms B. Compound B exhibits four singlets in its 1H NMR spectrum at 1.3 (6 H), 2.2 (3 H), 2.5 (2 H), and 3.8 (1 H) ppm. What is the structure of B?
Arrange the compounds in order of INCREASING reactivity towards bromination.
1. Toluene, Nitrobenzene, Anisole, Aniline
2. Acetanilide, Benzaldehyde, Toluene, Iodobenzene
3. Acetophenone, Bromobenzene, Aniline, Phenol
Galantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of
Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was
converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2
A. NaOH
MeO
D. DMP or PCC
G. HBr
MeO
B. H₂SO4, H₂O, HgSO4
E. Na2Cr₂O7, H₂SO4, H₂O
H. 1) O3; 2) DMS
H 2
The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary
reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there
is more than one correct solution, provide just one answer.
C. 1) BH3-THF; 2) H₂O2, NaOH
F.HBr, ROOR
I. TsCl, py
Meo
I₁,
N
Me
Galanthamine
OH
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- Galantamine, a natural product produced by the amaryllis family of flowering plants, has been used in the early treatment of Alzheimer's disease. In a synthesis of galantamine and related compounds (J. Org. Chem. 2015, 80, 1952-1956), compound 1 was converted into compound 2. Propose an efficient synthesis for the conversion of 1 to 2 A. NaOH MeO D. DMP or PCC G. HBr 1 MeO B. H₂SO4, H₂O, HgSO4 E. Na₂Cr₂O7, H₂SO4, H₂O H. 1) O3; 2) DMS H 2 x I. TsCl, py The conversion of 1 to 2 can be performed with some reagent or combination of the reagents listed below. Give the necessary reagents in the correct order for each transformation, as a string of letters (without spaces or punctuation, such as "EBF"). If there is more than one correct solution, provide just one answer. C. 1) BH3-THF; 2) H₂O2, NaOH F.HBr, ROOR = MeO Ill. N Me Galanthamine OHarrow_forwardhelp me pleasearrow_forwardWhen deuterated phenanthrene oxide undergoes a rearrangement in water to form a phenol, 81% of the deuterium is retained in the product a. What percentage of the deuterium is retained if an NIH shift occurs? b. What percentage of the deuterium is retained if an NIH shift does not occur?arrow_forward
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