2. (a) Consider the structure of compound 1 and the spectroscopic data given below. REDRAW compound 1 and assign ALL the spectroscopic data given DIRECTLY ON the molecule you have redrawn:

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
Chapter20: Dienes, Conjugated Systems, And Pericyclic Reactions
Section20.3: Uv-visible Spectroscopy
Problem 20.5P
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2.
(а)
Consider the structure of compound 1 and the spectroscopic data
given below. REDRAW compound 1 and assign ALL the
spectroscopic data given DIRECTLY ON the molecule you have
redrawn:
H
CH3
CH
CH;CH,CH,
`CH3
H
COMPOUND 1
IR
1720; 1640 and 1595 (two bands) cm
ΙΗ ΝMR
8 1.10 (3H, t, J= 7.30 Hz)
:
8 1.30 (6H, d, J= 7.50 Hz)
8 1.75 (2H, sextet, J= 7.30 Hz)
8 2.25 (2H, dq, J= 7.30, 1.80 Hz)
8 4.85 (1H, septet, J= 7.50 Hz)
8 5.85 (1H, dt, J = 15.50, 1.80 Hz)
8 7.70 (1H, dt, J= 15.50, 7.30 Hz)
[d = doublet; t= triplet; dt = doublet of triplets; dq = doublet of quartets]
Transcribed Image Text:2. (а) Consider the structure of compound 1 and the spectroscopic data given below. REDRAW compound 1 and assign ALL the spectroscopic data given DIRECTLY ON the molecule you have redrawn: H CH3 CH CH;CH,CH, `CH3 H COMPOUND 1 IR 1720; 1640 and 1595 (two bands) cm ΙΗ ΝMR 8 1.10 (3H, t, J= 7.30 Hz) : 8 1.30 (6H, d, J= 7.50 Hz) 8 1.75 (2H, sextet, J= 7.30 Hz) 8 2.25 (2H, dq, J= 7.30, 1.80 Hz) 8 4.85 (1H, septet, J= 7.50 Hz) 8 5.85 (1H, dt, J = 15.50, 1.80 Hz) 8 7.70 (1H, dt, J= 15.50, 7.30 Hz) [d = doublet; t= triplet; dt = doublet of triplets; dq = doublet of quartets]
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