Methadone a chiral synthetic compound used to treat opiate dependence and cancer pain is used as a racemicmixture. It is a central-acting analgesic that has a high affinity for u-opiod receptors. In humans, R (-)-methadone is about [25-50] fold more potent as an analgesic than its S (+) antipode.ofČENH₂CCH3Figure 1. MethadoneMethadone (Figure 1) is synthesized by alkylation of diphenylacetonitrile using 1-dimethylamino-2-propylchloride in the presence of sodium amide. The resulting 4-dimethylamino-2,2-dephenylvaleronitrile(Figure 2) is reacted with the ethylmagnesiumbromide and then hydrolyzed. This resulting racemate isseparated using (+)-tartaric acid, thus isolating (-)-methadoneCH3CHCH-CHI-N(H₂CCH3CH3-CH3NINH:CH₂-CH-CH₂-NCENCH3CH3-C-CH-CH₂-NCEOCH3C₂H5 MethadoneFigure 2CH3CH31.C₂HsMgBr2. H₂O1.1 How many stereoisomers can Methadone (Figure 1) have?1.2 What does the (-) sign in R(-)-Methadone mean?1.3 Draw the R isomer of Methadone (Figure 1) (explicitly show all stereochemical bonds aroundstereogenic center/s). Place numbers 1-4 (1-highest priority and 4 - lowest priority) around the groupssurrounding the stereogenic center/s1.4 Draw the S isomer of 4-dimethylamino-2,2-dephenylvaleronitrile (Figure 2)

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1.1 How many stereoisomers can Methadone (Figure 1) have? 1.2 What does the (-) sign in R(-)-Methadone mean? 1.3 Draw the R isomer of Methadone (Figure 1) (explicitly show all stereochemical bonds around stereogenic center/s). Place numbers 1-4 (1-highest priority and 4 - lowest priority) around the groups surrounding the stereogenic center/s 1.4 Draw the S isomer of 4-dimethylamino-2,2-dephenylvaleronitrile (Figure 2)

1.1 How many stereoisomers can Methadone (Figure 1) have? 1.2 What does the (-) sign in R(-)-Methadone mean? 1.3 Draw the R isomer of Methadone (Figure 1) (explicitly show all stereochemical bonds around stereogenic center/s). Place numbers 1-4 (1-highest priority and 4 - lowest priority) around the groups surrounding the stereogenic center/s 1.4 Draw the S isomer of 4-dimethylamino-2,2-dephenylvaleronitrile (Figure 2)

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

Chapter23: Amines

Section: Chapter Questions

Problem 23.71P

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