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Using the information for each compound below, A, B, C, and D, and the TLC information, calculate the index of hydrogen deficiency for each compound, A, B, C, D and determine their structures. Indicate the meaning of each bit of information. Calculate the Bf's for compounds A through G. Also give the structures of compounds E, F, and G. Compound A: CuHa (-)Bra, (+)KMNO, when heated "C NMR: 125ppm, 123ppm, 122ppm, 120ppm, 30ppm *HNMR: 7.7-7.5ppm complex splitting (2.5cm); 2ppm singlet (0.5cm) Compound B: C7H60 (+)Tollens, (+)KMNO, at room temperature, (-)FeCls, (-)Br. 1°C NMR: 210ppm, 135ppm, 130ppm, 128ppm, 126ppm *HNMR: 9.2ppm singlet (0.2cm), 7.8 - 7.3ppm complex splitting (1cm) Compound C: C10H1202 (-JBr2, (+)KMNO, at room temperature and when heated, (+) Lucas when heated "C NMR: 125ppm, 123ppm, 120ppm, 70ppm, 35ppm HNMR: 7.6-7.3ppm complex splitting (1.32cm); 4.4ppm broad lump (0.66cm), 3.5ppm triplet (0.66cm), 2.2ppm doublet (1.32cm) Compound D: C10H10 (+)Brz, (+)KMNO, at room temperature and when heated "C NMR: 128ppm, 126ppm, 124ppm, 115ppm, 38ppm A mixture of compounds A, B, C, and D from above is dissolved in a volatile solvent and the TLC is taken. It is shown to the left below. When the mixture is reacted with alkali KMno., (at room temperature and then heated), compound A yields compound E, compound B yields compound E, compound C yields compound F, and compound D yields compound G. The TLC of the mixture at the completion of this reaction is shown to the right. solvent front solvent front • B oe •E cm atarting line

Using the information for each compound below, A, B, C, and D, and the TLC information, calculate the index of hydrogen deficiency for each compound, A, B, C, D and determine their structures. Indicate the meaning of each bit of information. Calculate the Bf's for compounds A through G. Also give the structures of compounds E, F, and G. Compound A: CuHa (-)Bra, (+)KMNO, when heated "C NMR: 125ppm, 123ppm, 122ppm, 120ppm, 30ppm *HNMR: 7.7-7.5ppm complex splitting (2.5cm); 2ppm singlet (0.5cm) Compound B: C7H60 (+)Tollens, (+)KMNO, at room temperature, (-)FeCls, (-)Br. 1°C NMR: 210ppm, 135ppm, 130ppm, 128ppm, 126ppm *HNMR: 9.2ppm singlet (0.2cm), 7.8 - 7.3ppm complex splitting (1cm) Compound C: C10H1202 (-JBr2, (+)KMNO, at room temperature and when heated, (+) Lucas when heated "C NMR: 125ppm, 123ppm, 120ppm, 70ppm, 35ppm HNMR: 7.6-7.3ppm complex splitting (1.32cm); 4.4ppm broad lump (0.66cm), 3.5ppm triplet (0.66cm), 2.2ppm doublet (1.32cm) Compound D: C10H10 (+)Brz, (+)KMNO, at room temperature and when heated "C NMR: 128ppm, 126ppm, 124ppm, 115ppm, 38ppm A mixture of compounds A, B, C, and D from above is dissolved in a volatile solvent and the TLC is taken. It is shown to the left below. When the mixture is reacted with alkali KMno., (at room temperature and then heated), compound A yields compound E, compound B yields compound E, compound C yields compound F, and compound D yields compound G. The TLC of the mixture at the completion of this reaction is shown to the right. solvent front solvent front • B oe •E cm atarting line

Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
ChapterL4: Proton (1h) Nmr Spectroscopy
Section: Chapter Questions
Problem 4E
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Using the information for each compound below, A, B, C, and D, and the TLC information, calculate the index of hydrogen deficiency for each compound, A, B, C, D and determine their structures. Indicate the meaning of each bit of information. Calculate the BEs for compounds A through G. Also give the structures of compounds E, F, and G. Compound A: CuHa (-)Bra, (+)KMNO, when heated "C NMR: 125ppm, 123ppm, 122ppm, 120ppm, 30ppm *HNMR: 7.7-7.5ppm complex splitting (2.5cm); 2ppm singlet (0.5cm) Compound B: C7H60 (+)Tollens, (+)KMNO, at room temperature, (-)FeCl,, (-)Br. 1°C NMR: 210ppm, 135ppm, 130ppm, 128ppm, 126ppm HNMR: 9.2ppm singlet (0.2cm), 7.8 - 7.3ppm complex splitting (1cm) Compound C: C10H1202 (-JBr2, (+)KMNO, at room temperature and when heated, (+) Lucas when heated "C NMR: 125ppm, 123ppm, 120ppm, 70ppm, 35ppm HNMR: 7.6-7.3ppm complex splitting (1.32cm); 4.4ppm broad lump (0.66cm), 3.5ppm triplet (0.66cm), 2.2ppm doublet (1.32cm) Compound D: C10H10 (+)Brz, (+)KMNO, at room temperature and when heated "C NMR: 128ppm, 126ppm, 124ppm, 115ppm, 38ppm A mixture of compounds A, B, C, and D from above is dissolved in a volatile solvent and the TLC is taken. It is shown to the left below. When the mixture is reacted with alkali KMno., (at room temperature and then heated), compound A yields compound E, compound B yields compound E, compound C yields compound F, and compound D yields compound G. The TLC of the mixture at the completion of this reaction is shown to the right. solvent front solvent front • B •E cm starting line starting line
Transcribed Image Text:Using the information for each compound below, A, B, C, and D, and the TLC information, calculate the index of hydrogen deficiency for each compound, A, B, C, D and determine their structures. Indicate the meaning of each bit of information. Calculate the BEs for compounds A through G. Also give the structures of compounds E, F, and G. Compound A: CuHa (-)Bra, (+)KMNO, when heated "C NMR: 125ppm, 123ppm, 122ppm, 120ppm, 30ppm *HNMR: 7.7-7.5ppm complex splitting (2.5cm); 2ppm singlet (0.5cm) Compound B: C7H60 (+)Tollens, (+)KMNO, at room temperature, (-)FeCl,, (-)Br. 1°C NMR: 210ppm, 135ppm, 130ppm, 128ppm, 126ppm HNMR: 9.2ppm singlet (0.2cm), 7.8 - 7.3ppm complex splitting (1cm) Compound C: C10H1202 (-JBr2, (+)KMNO, at room temperature and when heated, (+) Lucas when heated "C NMR: 125ppm, 123ppm, 120ppm, 70ppm, 35ppm HNMR: 7.6-7.3ppm complex splitting (1.32cm); 4.4ppm broad lump (0.66cm), 3.5ppm triplet (0.66cm), 2.2ppm doublet (1.32cm) Compound D: C10H10 (+)Brz, (+)KMNO, at room temperature and when heated "C NMR: 128ppm, 126ppm, 124ppm, 115ppm, 38ppm A mixture of compounds A, B, C, and D from above is dissolved in a volatile solvent and the TLC is taken. It is shown to the left below. When the mixture is reacted with alkali KMno., (at room temperature and then heated), compound A yields compound E, compound B yields compound E, compound C yields compound F, and compound D yields compound G. The TLC of the mixture at the completion of this reaction is shown to the right. solvent front solvent front • B •E cm starting line starting line
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