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Interpretation:
The details of the mechanism for the reaction between mixed anhydride and Z-Ala-Leu, and how carbon dioxide and ethanol are formed in the mechanisms are to be discussed.
Concept introduction:
The reaction between nucleophile and acyl compounds is called nucleophilic acyl substitution.
Nucleophilic acyl substitution describe a class of substitution reactions involving nucleophiles and acyl compounds. In this type of reaction, a nucleophile—such as an alcohol, amine, or enolate—displaces the leaving group of an acyl derivative—such as an acid halide, anhydride, or ester.
A mixed anhydride is a
Acid chlorides react with
The carboxylic acid is converted into acid chlorides in the presence of thionyl chloride.
Decarboxylation is the loss of carbon dioxide.
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Chapter 17 Solutions
ORGANIC CHEMISTRY-ETEXT REG ACCESS
- A chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug for the control of gastric acidity and peptic ulcers. Cimetidine reduces gastric acid secretion by inhibiting the interaction of histamine with gastric H2 receptors. In the development of this drug, a cyano group was added to the substituted guanidino group to alter its basicity. Do you expect this modified guanidino group to be more basic or less basic than the guanidino group of arginine? Explain.arrow_forward18-48 4-Aminobenzoic acid is prepared from benzoic acid by the following two steps. Show reagents and experimental conditions to bring about each step.arrow_forward(a) Predict the product of the reaction of KOH with 1-amino propane. (b) Predict the product of a deprotonated ethanol (an “ethanolate anion", O-CH2-CH3) with phenol (hydroxybenzene). (c) Predict the product of propanoic acid with deprotonated ethanol (an “ethanolate anion", O-CH2-CH3).arrow_forward
- H NH₂ ཡིནྣཾ ༥ ཨ ཨནྡྷ༥ ༠ ཨི་ཝཱ, ཙ ཨ་ར༩ H NH3+ the acidity of the amine ion drives the reaction to shift toward the conjugate base of the carboxylic acid product. the resulting carboxylic acid ion is a weaker base than an acetate ion. O aldehydes are more reactive toward nucleophiles than ketones. Onucleophilic attack occurs preferentially at the less hindered carbon of the formyl group.arrow_forward1. Create a flowchart for the synthesis and purification of phenacetin. Draw out your steps for the extraction process and label the organic and aqueous layers in your diagrams. Indicate where the product is in each step. 2. Draw the mechanism for the deprotonation of the phenol group of acetaminophen by potassium carbonate. Label the acid, base, conjugate acid and conjugate base. How do you know potassium carbonate is a strong enough base to do this deprotonation?arrow_forwardDefine the Mechanism - Conversion of Carboxylic Acids to Amides with DCCarrow_forward
- Based on the image attached, it shows methyl salicylate reacts with Ethanamine, and Ether act as a solvent to form N-ethylbenzamide as a product. Explains the mechanism reaction of conversion ester to an amide.arrow_forwardThe deuterium kinetic isotope effect (kH2O/kD2O) for the hydrolysis of aspirin is 2.2. What does this tell you about the kind of catalysis exerted by the ortho-carboxyl substituent? (Hint: It is easier to break an O¬H bond than an O¬D bond.)arrow_forwardExplain the products that would be formed when cholesterol is reacted with bromine in an organic solvent. Outline a mechanism for the reaction that takes place.arrow_forward
- но- OH + HO-CH3 но -CH3 + H20 phosphoric acid methanol methyl phosphate water Formation of a phosphate ester Assuming phosphoric acid undergoes a similar reaction to that of carboxylic acids, outline a mechanism for the formation of methylphosphate. Formation of phosphate esters generally does not require the addition of a mineral acid catalyst the way Fischer esterifications do. Explain why this is so.arrow_forwardA student decided to run the esterification reaction between p-toluic acid (p-methylbenzoic) and ethanol but found that the stockroom had only just enough ethanol left to react with her carboxylic acid, that is, a stoichiometric amount of alcohol. Furthermore, the only concentrated acid the stockroom had left was hydrochloric acid (a non-dehydrating acid ). What other method (s) could she use to drive the esterification reaction to completion ?arrow_forward27) Hydrolysis of an ester: O II CH,-C-O-CH2-CH2-CH, + H20 28) Acid/ Base reaction of an amine CH3-CH2-NH2 H2CO3 29) Hydrolysis of an amide 11 CH3-CH2-CH2-CH2-CH2-C-NH-CH2-CH2-CH, + H20 OMIC Moleculesarrow_forward
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- Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
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