Concept explainers
Interpretation:
To identify the functional groups in Warfarin.
Concept Introduction:
A group of atoms which are responsible for the
A stereo centre is the centre where all the 4 groups attached to a carbon are different.
A keto group stays in the equilibrium with its enol (−OH) form by resonance.
NaBH4 is a reducing agent it reduces
Interpretation:
To draw the stereorepresentation of the r enantiomer as s enantiomer is more active than r enantiomer.
Concept Introduction:
A stereo centre is the centre where all the 4 groups attached to a carbon are different.
A keto group stays in the equilibrium with its enol (−OH) form by resonance.
NaBH4 is a reducing agent it reduces ketone or aldehyde to an alcohol.
Interpretation:
To draw the structural formula of keto form of Warfarin.
Concept Introduction:
A stereo centre is the centre where all the 4 groups attached to a carbon are different.
A keto group stays in the equilibrium with its enol (−OH) form by resonance.
NaBH4 is a reducing agent it reduces ketone or aldehyde to an alcohol.
Interpretation:
To draw the product formed by treating warfarin with NaBH4..
Concept Introduction:
A stereo centre is the centre where all the 4 groups attached to a carbon are different.
A keto group stays in the equilibrium with its enol (−OH) form by resonance.
NaBH4 is a reducing agent it reduces ketone or aldehyde to an alcohol.
Interpretation:
The number of molecules of warfarin present in 4 mg tablet should be determined.
Concept Introduction:
A stereo centre is the centre where all the 4 groups attached to a carbon are different.
A keto group stays in the equilibrium with its enol (−OH) form by resonance.
NaBH4 is a reducing agent it reduces ketone or aldehyde to an alcohol.
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Chapter 17 Solutions
Introduction to General, Organic and Biochemistry
- 16-58 Following is a structural formula of desosamine, a sugar component of several macrolide antibiotics, including the erythromycins. The configuration shown here is that of the natural product. Erythromycin is produced by a strain of Streptomyces erythreus originally found in a soil sample from the Philippine Archipelago. ch3 T Desosamine Name all the functional groups in desosamine. (Chapter 10) How many stereocenters are present in desosamine? How many stereoisomers are possible for it? How many pairs of enantiomers are possible for it? Draw the alternative chair conformations for desosamine and label which groups are equatorial and which are axial. (d > Which of the alternative chair conformations for desosamine is more stable?arrow_forward17-54 Following is the structure of immunosuppressant FK-506, a molecule shown to disrupt calcineurin-mediated signal transduction in T-lymphocytes. (a) There are three carbon—carbon double bonds present in this molecule. Which of the three has the potential for cis/trans isomerism? Assign a cis or trans con?guration to each carbon-carbon double bond that has this possibility. (b) How many stereocenters are present in this molecule? How many stereoisomers are possible for it? (c) Are there any aromatic components in this molecule? (d) Consider the two carbon atoms marked with asterisks. Assign an R or S con?guration of each stereocenter. (e) Because of the presence of a 21-member ring, this molecule is described as a macrocycle. This ring is fashioned by three types of bonds, several carbon-carbon bonds, one ester, one hemiacetal, and one amide. Locate the ester and the hemiacetal. (f) Draw the structural formula of the long chain compound that would result if the hemiacetal were to be cleaved to an alcohol and a carbonyl group.arrow_forward18-18 Propanoic acid and methyl acetate are constitutional isomers, and both are liquids at room temperature. One of these compounds has a boiling point of 141°C; the other has a boiling point of 57°C. Which compound has which boiling point? Explain.arrow_forward
- 16-54 Several poisonous plants, including Atropa belladonna, contain the alkaloid atropine. The name “belladonna” (which means “beautiful lady”) probably comes from the fact that Roman women used extracts from this plant to make themselves more attractive. Atropine is widely used by ophthal mologists and optometrists to dilate the pupils for eye examination. Classify the amino group in atropine as primary, secondary, or tertiary. Locate all stereocenters in atropine. Account for the fact that atropine is almost insoluble in water (1 g in 455 mL of cold water) but atropine hydrogen sulfate is very soluble (1 g in 5 mL of cold water). Account for the fact that a dilute aqueous solution of atropine is basic (pH approximately 10.0).arrow_forward16-28 Following is the structural formula of metformin, the hydrochloride salt of which is marketed as the antidiabetic medication Glucophage. Metformin was introduced into clinical practice in the United States in 1995 for the treatment of type 2 diabetes. More than 25 million prescriptions for this drug were written in 2000, making it the most commonly prescribed brand-name diabetes medication in the nation. NH NH H3(\ 3 N N Nh2ch3 h Metformin Complete the Lewis structure for metformin, showing all valence electrons. Which nitrogen is the most likely site of protonation? Draw the structural formula of Glucophage.arrow_forward15-10 Define the term “stereoisomer.” Name three types of stereoisomers.arrow_forward
- 17-15 Draw structural formulas for the four aldehydes with the molecular formula C5H10O. Which of these aldehydes are chiral?arrow_forward17-29 Why can’t two molecules of acetone form a hydrogen bond with each other?arrow_forward17-12 Is it possible for the carbon atom of a carbonyl group to be a stereocenter? Explain.arrow_forward
- 17-74 Glucose, C6H12O6, contains an aldehyde group but exists predominantly in the form of the cyclic hemiacetal shown here. We will discuss this cyclic form of glucose in Chapter 20. A cyclic hemiacetal is formed when the —OH group of one carbon bonds to the carbonyl group of another carbon. (a) Which carbon in glucose provides the —OH group and which provides the —CHO group? (b) Draw the alternative chair confirmations of D-glucose and state which of the two is the more stable.arrow_forwardLabel each of the following structures as a cyclic hemiacetal, hemiketal, acetal, ketal, or none of these: a. b. c.arrow_forward17-47 What is the characteristic structural feature of a hemiacetal? Of an acetal?arrow_forward
- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning