Organic Chemistry-Package(Custom)
4th Edition
ISBN: 9781259141089
Author: SMITH
Publisher: MCG
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Chapter 23, Problem 23.55P
Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that
have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps
from the chiral
configuration of the enantiomer formed by this route as
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Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral α-hydroxy acid A. Identify B and C in the following reaction sequence, and designate the configuration of the enantiomer formed by this route as R or S.
Clopidogrel is the generic name for Plavix, a drug used to prevent the formation of blood clots in patients that have a history of heart attacks or strokes. A single enantiomer of clopidogrel can be prepared in three steps from the chiral αhydroxy acid A. Identify B and C in the following reaction sequence, and designate the conguration of the enantiomer formed by this route as R or S.
An acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2-phenylpropanoic acid forms two products having different melting pointsand somewhat different solubilities. Draw the structure of these twoproducts. Assign R and S to any stereogenic centers in the products.How are the two products related? Choose from enantiomers,diastereomers, constitutional isomers, or not isomers of each other.
Chapter 23 Solutions
Organic Chemistry-Package(Custom)
Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.3PCh. 23 - Prob. 23.4PCh. 23 - Which CH bonds in the following molecules are...Ch. 23 - Prob. 23.6PCh. 23 - Prob. 23.7PCh. 23 - When ethyl acetoacetate (CH3COCH2CO2CH2CH3) is...Ch. 23 - Prob. 23.9PCh. 23 - Prob. 23.10P
Ch. 23 - Prob. 23.11PCh. 23 - Problem 23.11 Draw the products of each...Ch. 23 - Problem 23.12 Draw the products of each reaction....Ch. 23 - Prob. 23.14PCh. 23 - Prob. 23.15PCh. 23 - Prob. 23.16PCh. 23 - Prob. 23.17PCh. 23 - Prob. 23.18PCh. 23 - Problem 23.18 How can pentan-2-one be converted...Ch. 23 - Problem 23.19 Identify A, B, and C, intermediates...Ch. 23 - Prob. 23.21PCh. 23 - Problem 23.21 Draw the products of each...Ch. 23 - Prob. 23.23PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Prob. 23.25PCh. 23 - Prob. 23.26PCh. 23 - Prob. 23.27PCh. 23 - Prob. 23.28PCh. 23 - Prob. 23.29PCh. 23 - 23.29 Draw enol tautomer(s) for each compound....Ch. 23 - 22.30 The cis ketone A is isomerized to a trans...Ch. 23 - Draw enol tautomers for each compound. a. b. c.Ch. 23 - Prob. 23.33PCh. 23 - What hydrogen atoms in each compound have a pKa25?...Ch. 23 - Rank the labeled protons in each compound in order...Ch. 23 - Prob. 23.36PCh. 23 - Prob. 23.37PCh. 23 - Prob. 23.38PCh. 23 - Prob. 23.39PCh. 23 - 23.38 Acyclovir is an effective antiviral agent...Ch. 23 - Prob. 23.41PCh. 23 - 23.39 Explain why forms two different alkylation...Ch. 23 - 23.41 Acid-catalyzed bromination of pentanone ...Ch. 23 - Draw a stepwise mechanism for each reaction. a. b.Ch. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Use the malonic ester synthesis to prepare each...Ch. 23 - 23.45 Devise a synthesis of valproic acid , a...Ch. 23 - Synthesize each compound from diethyl malonate....Ch. 23 - Prob. 23.49PCh. 23 - What alkyl halides are needed to prepare each...Ch. 23 - Synthesize each compound from ethyl acetoacetate....Ch. 23 - Draw the organic products formed in each reaction....Ch. 23 - 23.51 Draw the products formed (including...Ch. 23 - Prob. 23.54PCh. 23 - 23.54 Clopidogrel is the generic name for Plavix,...Ch. 23 - 23.55 What reaction conditions—base, solvent, and...Ch. 23 - Explain why each of the following reactions will...Ch. 23 - Prob. 23.58PCh. 23 - 23.57 Draw a stepwise mechanism showing how two...Ch. 23 - 23.58 Draw a stepwise mechanism for the following...Ch. 23 - Prob. 23.61PCh. 23 - 23.60 Draw stepwise mechanisms illustrating how...Ch. 23 - Prob. 23.63PCh. 23 - Prob. 23.64PCh. 23 - Convert acetophenone (C6H5COCH3) into each of the...Ch. 23 - Prob. 23.66PCh. 23 - Prob. 23.67PCh. 23 - Prob. 23.68PCh. 23 - Synthesize each product from ethyl acetoacetate...Ch. 23 - Prob. 23.70PCh. 23 - Prob. 23.71PCh. 23 - 23.68 Capsaicin, the spicy component of hot...Ch. 23 - 23.69 Treatment of W with , followed by , affords...Ch. 23 - Prob. 23.74PCh. 23 - Prob. 23.75PCh. 23 - Prob. 23.76PCh. 23 - Prob. 23.77PCh. 23 - Prob. 23.78P
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- Following is a retrosynthesis for the coronary vasodilator ganglefene. (a) Propose a synthesis for ganglefene from 4-hydroxybenzoic acid and 3-methyl-3-buten-2-one. (b) Is ganglefene chiral? If so, which of the possible stereoisomers are formed in this synthesis?arrow_forwardAn acid–base reaction of (R)-sec-butylamine with a racemic mixture of 2phenylpropanoic acid forms two products having different melting points and somewhat different solubilities. Draw the structure of these two products. Assign R and S to any stereogenic centers in the products. How are the two products related? Choose from enantiomers, diastereomers, constitutional isomers, or not isomers of each other.arrow_forwardTreatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.arrow_forward
- When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in position 2 are incubated with citrate synthase, an enzyme of the tricarboxylic acid cycle, only the following enantiomer of [2-l4C]citric acid is formed stereoselectively. Note that citric acid containing only 12C is achiral. Assign an R or S configuration to this enantiomer of [2-14C]citric acid. (Note: Carbon-14 has a higher priority than carbon-12.)arrow_forwardDescribe the stereochemistry of the bromohydrin formed in each reaction (each reaction is stereospecific). (a) cis-3-Hexene + Br2/H2O (b) trans-3-Hexene + Br2/H2Oarrow_forwardTwo diastereomeric sets of enantiomers, A/B and C/D, exist for 3-bromo-2-butanol. When enantiomer A or B is treated with HBr, only racemic 2,3-dibromobutane is formed; no meso isomer is formed. When enantiomer C or D is treated with HBr, only meso 2,3-dibromobutane is formed; no racemic 2,3-dibromobutane is formed. Account for these observations.arrow_forward
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