Compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm and shows a single absorption in the proton NMR spectrum at 8 3.00. When heated gently with methanol, compound B, C,H,O,, is obtained. Compound B has IR absorptions at 2500–3000 (broad), 1730, and 1701 cm-, and its proton NMR spectrum in D,0 consists of resonances at & 2.7 (complex splitting) and & 3.7 (a singlet) in the intensity ratio 4:3. Give the structures A and B, omitting stereochemistry.
Compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm and shows a single absorption in the proton NMR spectrum at 8 3.00. When heated gently with methanol, compound B, C,H,O,, is obtained. Compound B has IR absorptions at 2500–3000 (broad), 1730, and 1701 cm-, and its proton NMR spectrum in D,0 consists of resonances at & 2.7 (complex splitting) and & 3.7 (a singlet) in the intensity ratio 4:3. Give the structures A and B, omitting stereochemistry.
Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter21: Benzene And The Concept Of Aromaticity
Section: Chapter Questions
Problem 21.26P: Compound I (C11H14O2) is insoluble in water, aqueous acid, and aqueous NaHCO3, but dissolves readily...
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![Compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm and shows a single absorption in the
proton NMR spectrum at 8 3.00. When heated gently with methanol, compound B, C,H,O,, is obtained. Compound B
has IR absorptions at 2500–3000 (broad), 1730, and 1701 cm-, and its proton NMR spectrum in D,0 consists of
resonances at & 2.7 (complex splitting) and & 3.7 (a singlet) in the intensity ratio 4:3. Give the structures A and B,
omitting stereochemistry.](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Ff140a581-3fa5-49f7-a0c3-bdc8f7e4514c%2F21871876-fc69-4ecf-a3af-6a44ba48bc88%2Fu7dc6t8.bmp&w=3840&q=75)
Transcribed Image Text:Compound A has prominent infrared absorptions at 1050, 1786, and 1852 cm and shows a single absorption in the
proton NMR spectrum at 8 3.00. When heated gently with methanol, compound B, C,H,O,, is obtained. Compound B
has IR absorptions at 2500–3000 (broad), 1730, and 1701 cm-, and its proton NMR spectrum in D,0 consists of
resonances at & 2.7 (complex splitting) and & 3.7 (a singlet) in the intensity ratio 4:3. Give the structures A and B,
omitting stereochemistry.
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