The hydronaphthacene ring system consists of five fused six-membered rings, as shown below in compounds 3 and 4. One method forconstruction 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 onechiral center.SiMe,Cr(CO)5OMeMe,SiHO2CHOMe,Si1SiMe,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.

Ans) Compound 4 has an internal plane of symmetry, so it has fewer signals in its 13C NMR spectrum.

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)

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)

Chemistry

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ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Concept explainers

Organomagnesium compounds

The interaction of alkyl halide with Mg metal in a suitable ether solvent is the common method for the synthesis of the Grignard reagent.

Hydrolysis Grignard Reactions and Reduction

Organomagnesium halides are Grignard reagents. Francois Auguste Victor Grignard, a French chemist who received the Nobel Prize in Chemistry in 1912, created these highly useful reagents.

Question

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.

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