Compound D 3 overlapping singlets, integrating for 3H, each (total of 9H) 2H, quartet 3H triplet 8 7 6 5 3 Z 1 C Compound E ) 8 00 7 3 overlapping singlets, integrating for 3H, each (total of 9H) 1H 1H 1H IT 6 5 3 N. 0 11. (10 pts) You've been given an unknown alkane in the lab (compound ✗) its molecular formula is C7H16. When reacting X with Br2/hv, three different products are formed: A, B and C. A and B were each reacted separately with NaOEt/EtOH and you find that they both give the same product, D (C7H14, 1H NMR on next page). When C reacts with tBuOK/tBuOH, E is formed (C7H12, 1H 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 by drawing the structure and adding peak assignments using a clear lettering system for compounds D and E.
Compound D 3 overlapping singlets, integrating for 3H, each (total of 9H) 2H, quartet 3H triplet 8 7 6 5 3 Z 1 C Compound E ) 8 00 7 3 overlapping singlets, integrating for 3H, each (total of 9H) 1H 1H 1H IT 6 5 3 N. 0 11. (10 pts) You've been given an unknown alkane in the lab (compound ✗) its molecular formula is C7H16. When reacting X with Br2/hv, three different products are formed: A, B and C. A and B were each reacted separately with NaOEt/EtOH and you find that they both give the same product, D (C7H14, 1H NMR on next page). When C reacts with tBuOK/tBuOH, E is formed (C7H12, 1H 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 by drawing the structure and adding peak assignments using a clear lettering system for compounds D and E.
Chapter12: Structure Determination: Mass Spectrometry And Infrared Spectroscopy
Section12.SE: Something Extra
Problem 46AP: Ketones undergo a reduction when treated with sodium borohydride, NaBH4. What is the structure of...
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Transcribed Image Text:Compound D
3 overlapping
singlets,
integrating for 3H,
each (total of 9H)
2H,
quartet
3H
triplet
8
7
6
5
3
Z
1
C
Compound E
)
8
00
7
3 overlapping singlets,
integrating for 3H, each
(total of 9H)
1H
1H
1H
IT
6
5
3
N.
0
Transcribed Image Text:11. (10 pts) You've been given an unknown alkane in the lab (compound ✗) its molecular
formula is C7H16. When reacting X with Br2/hv, three different products are formed: A, B
and C.
A and B were each reacted separately with NaOEt/EtOH and you find that they both give the
same product, D (C7H14, 1H NMR on next page).
When C reacts with tBuOK/tBuOH, E is formed (C7H12, 1H 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 by drawing the structure
and adding peak assignments using a clear lettering system for compounds D and E.
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