(a)
Interpretation:
The synthesis of propranolol has to be shown from 1-naphthol.
(b)
Interpretation:
The chirality of Propranolol is to be identified and the possible stereoisomers has to be identified in the given synthesis.
Concept introduction:
Chiral:
A molecule is non superimposable on its mirror image is called chiral molecule.
Four different atoms attached to a carbon atom is called chiral molecule.
Isomer:
A molecule having the same molecular formula but with different chemical structure is called isomer.
Stereoisomers:
Stereoisomers are molecules that have the same molecular formula and they differ only in arrangement of atom in three-dimensional space.
Enantiomers:
A compound which is non-superimposable mirror image is called enantiomers.
Diastereomers:
A compound which is non-superimposable and non-mirror image is called diastereomers.
Racemic mixture:
A racemic mixture is simply a mixture containing an equal amount of each enantiomer.
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Chapter 21 Solutions
Organic Chemistry
- The start drug is Tolbutamide and the product is Chlorpropamide. Which of the following is incorrect? a. the -CH3 groyp is replaced with Cl atom to prevent oxidation of –CH3 group b. The -CH3 group in Tolbutamidw can be easily oxidized into -CH20H, and then to –CO2H c. this modification is used to prolong the duration of action of chlorpropamide d. this modification is achieved by an oxygen enzyme e. none of the abovearrow_forwardThe following molecule undergoes an intramolecular reaction in the presence of pyrrolidinium acetate, the protonated form of pyrrolidine. Draw the product of this reaction, assuming that a dehydration reaction takes place.arrow_forwardWhat is the main reaction mechanism for this reductive amination?arrow_forward
- Which of the following statement is INCORRECT? a. Electron-withdrawing group near the carboxylate ion reduces its stability thereby acidity is reduced. b. Electron-withdrawing group near the carboxylate ion increase acidity and also contributes to the stability. c. Electron-donating groups decrease acidity by destabilizing the carboxylate ion. d. A carboxylate ion is much more stable than the corresponding alkoxide ion because of the existence of resonance structures for the carboxylate ion which disperse its negative charge.arrow_forwardDuring the decarboxylation of acetoacetate, what is the nucleophile and what is the electrophile? Is the formation of a schiff base simply a preparation step or is the formation of a schiff base formed also by nucleophile/electrophile interaction?arrow_forwardThe hydrolysis of the ester shown here is catalyzed by morpholine. Explain how morpholine catalyzes the reaction. (Hint: The pKa of the conjugateacid of morpholine is 9.3, so morpholine is too weak a base to function as a base catalyst.)arrow_forward
- What is difference between the acetoacetic and malonic ester syntheses? Provide an example of each, including all intermediates..arrow_forward1) How will you describe whether any compound has been oxidized or reduced? Support the answer with suitable examples. 2)Why carboxylic acid with a carbonyl group at 3rd position can be decarboxylated? 3) Explain why electrophilic aromatic substitution in Pyrrole takes place at C-2 positions whereas, in Pyridine it takes place at C-3 position? 4) List the following esters in order of decreasing reactivities towards hydrolysis with reason: Methyl benzoate, p-cyano methyl benzoate and p-hydroxy methyl benzoate 5)LDA is the base of choice for carbonyl compound to completely convert into enolate. Why?arrow_forwardThe reaction that occurs when the benzaldehyde you have is reacted in a basic environment is called the Cannizzaro reaction, and when it is reacted with cyanide, it is called benzoin. It Explain the reason by writing the reaction mechanisms of the reactions.arrow_forward
- Following is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. You have not studied the Baeyer-Villiger reaction (D to E). The mechanism involves nucleophilic reaction of the peroxyacid with the carbonyl followed by a rearrangement much like that involved in the hydroboration reaction ). Write a mechanism for this reaction.arrow_forwardFollowing is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. The tributyltin hydride, Bu3SnH, used in the conversion of (H) to (I) reacts via a radical chain reaction; the first step involves a reaction with a radical initiator to form Bu3Sn?. Suggest a mechanism for the rest of the reaction.arrow_forwardFollowing is an outline of the stereospecific synthesis of the “Corey lactone.” Professor E. J. Corey (Harvard University) describes it this way. “The first general synthetic route to all the known prostaglandins was developed by way of bicycloheptene intermediates. The design was guided by the requirements that the route be versatile enough to allow the synthesis of many analogs and also allow early resolution. This synthesis has been used on a large scale and in laboratories throughout the world; it has been applied to the production of countless prostaglandin analogs. Note: The wavy lines in compound C indicate that the stereochemistry of -Cl and -CN groups was not determined. Q. What is the function of sodium hydride, NaH, in the first step? What is the pK a of cyclopentadiene? How do you account for its remarkable acidity?arrow_forward
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