Question 3 Use the provided spectral data to determine the structure of the aromatic compound. Propose a synthesis from benzene in 5 steps or less. 200 oho, DEPT O out s 200 160 HNMR Sem 10 HNMR: 6.72 ppm (1H, d). 6.64 ppm (TH, s). 6.63 pom (TH d), 2.02 ppm (3H, s). 1.93 ppm (3H, s), 1.92 (3H, s) Answer 3

Organic Chemistry
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ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter15: Benzene And Aromaticity
Section15.SE: Something Extra
Problem 53AP: Consider the aromatic anions below and their linear counterparts. Draw all of the resonance forms...
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Question 3
Use the provided spectral data to determine the structure of the aromatic compound. Propose a synthesis from
benzene in 5 steps or less.
Spe
DEPT O out od
T
200
160
120
HNR Speu
10
6 5 43
HNMR: 6.72 ppm (1H, d) 6.64 ppm (1H, s). 6.63 pom (TH d). 2.02 ppm (3H, s). 1.93 ppm (3H, s), 1.92 (3H,
s)
Answer 3
Proposed Synthesis:
1. CH,BriFeBr,
2. Bra. ight
3. N
4. LIAIH.
5. HO
6. CHI (xs)
7. Ag.0, H,O
8. heat
Transcribed Image Text:Question 3 Use the provided spectral data to determine the structure of the aromatic compound. Propose a synthesis from benzene in 5 steps or less. Spe DEPT O out od T 200 160 120 HNR Speu 10 6 5 43 HNMR: 6.72 ppm (1H, d) 6.64 ppm (1H, s). 6.63 pom (TH d). 2.02 ppm (3H, s). 1.93 ppm (3H, s), 1.92 (3H, s) Answer 3 Proposed Synthesis: 1. CH,BriFeBr, 2. Bra. ight 3. N 4. LIAIH. 5. HO 6. CHI (xs) 7. Ag.0, H,O 8. heat
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