27. You've been given an unknown alkane in the lab (compound X) its molecular formula is C7H16. When reacting X with Br2/hv, three different products are formed: A, B and C. A and B are were each reacted separately with NaOEt/EtOH and you find that they both give the same product, D (C7H14, 'H NMR on next page). When C reacts with tBuOK/tBuOH, E is formed (C7H12, 'H NMR on next page). E can then react with ethylene and heat to form the Diels-Alder product F (given). compound F Provide structures for X, A, B, C, D, and E in a clearly labeled roadmap/reaction scheme in the space below. Then, label the NMRS on the next page with proper assignments using a clear lettering system for compounds D and E.

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
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.53P
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27. You've been given an unknown alkane in the lab (compound X) its molecular formula is
C7H16. When reacting X with Br2/hv, three different products are formed: A, B and C.
A and B are were each reacted separately with NaOEt/ETOH and you find that they both give the
same product, D (C7H14, 'H NMR on next page).
When C reacts with (BUOK/ABUOH, E is formed (C7H12, 'H NMR on next page). E can
then react with ethylene and heat to form the Diels-Alder product F (given).
compound F
Provide structures for X, A, B, C, D, and E in a clearly labeled roadmap/reaction
scheme in the space below. Then, label the NMRS on the next page with proper assignments
using a clear lettering system for compounds D and E.
Transcribed Image Text:27. You've been given an unknown alkane in the lab (compound X) its molecular formula is C7H16. When reacting X with Br2/hv, three different products are formed: A, B and C. A and B are were each reacted separately with NaOEt/ETOH and you find that they both give the same product, D (C7H14, 'H NMR on next page). When C reacts with (BUOK/ABUOH, E is formed (C7H12, 'H NMR on next page). E can then react with ethylene and heat to form the Diels-Alder product F (given). compound F Provide structures for X, A, B, C, D, and E in a clearly labeled roadmap/reaction scheme in the space below. Then, label the NMRS on the next page with proper assignments using a clear lettering system for compounds D and E.
Compound E
3 overlapping singlets,
integrating for 3H, each
(total of 9H)
1H
1H
1H
T
8.
5
3
2
1
Compound D
6.
5
4
3
1
-0-
Transcribed Image Text:Compound E 3 overlapping singlets, integrating for 3H, each (total of 9H) 1H 1H 1H T 8. 5 3 2 1 Compound D 6. 5 4 3 1 -0-
Expert Solution
Step 1

In the given problem, an alkane X having a molecular formula of C7H16 undergoes the bromination reaction in the presence of sunlight to form three products mainly A, B and C. The compound A and B on treating with NaOEt in the presence of EtOH will yield a same product namely D with molecular formula C7H14 while the compound C on reacting with NaOEt in the presence of EtOH will yield a product E with molecular formula C7H12

The product E formed will reacts with ethylene to give Diels elder product F whose structure is given in the question. 

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