The hydronaphthacene ring system consists of five fused six-membered rings, as shown below in compounds 3 and 4. One method for construction of this ring system involves treatment of compound 1 with an organometallic reagent such as 2, called a Fischer carbene. (Tetrahedron Lett. 2011, 52, 4182-4185). Two diastereomeric products are obtained, 3 and 4, differing only in the configuration at one chiral center. SiMe, Cr(CO)5 OMe Me,Si HO CHO 1 Me,Si SiMeg 3 - (R) 4 - (S)

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The hydronaphthacene ring system consists of five fused six-membered rings, as shown below in compounds 3 and 4. One method for
construction of this ring system involves treatment of compound 1 with an organometallic reagent such as 2, called a Fischer carbene.
(Tetrahedron Lett. 2011, 52, 4182-4185). Two diastereomeric products are obtained, 3 and 4, differing only in the configuration at one
chiral center.
SiMe,
Cr(CO)5
OMe
Me,Si
HO
2
CHO
Me,Si
1
SiMe,
3 - (R)
4 - (S)
Transcribed Image Text:The hydronaphthacene ring system consists of five fused six-membered rings, as shown below in compounds 3 and 4. One method for construction of this ring system involves treatment of compound 1 with an organometallic reagent such as 2, called a Fischer carbene. (Tetrahedron Lett. 2011, 52, 4182-4185). Two diastereomeric products are obtained, 3 and 4, differing only in the configuration at one chiral center. SiMe, Cr(CO)5 OMe Me,Si HO 2 CHO Me,Si 1 SiMe, 3 - (R) 4 - (S)
Select the choice(s) that describes how you could distinguish these two products using only 1³C NMR (select all that apply).
O Compound 4 lacks an internal plane of symmetry, so it has a greater number of signals in its 13C NMR spectrum.
O Compound 4 has an internal plane of symmetry, so it has fewer signals in its 13C NMR spectrum.
O Compound 3 lacks an internal plane of symmetry, so it has a greater number of signals in its 13C NMR spectrum.
O Compound 3 has an internal plane of symmetry, so it has fewer signals in its 13C NMR spectrum.
Transcribed Image Text:Select the choice(s) that describes how you could distinguish these two products using only 1³C NMR (select all that apply). O Compound 4 lacks an internal plane of symmetry, so it has a greater number of signals in its 13C NMR spectrum. O Compound 4 has an internal plane of symmetry, so it has fewer signals in its 13C NMR spectrum. O Compound 3 lacks an internal plane of symmetry, so it has a greater number of signals in its 13C NMR spectrum. O Compound 3 has an internal plane of symmetry, so it has fewer signals in its 13C NMR spectrum.
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