Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
expand_more
expand_more
format_list_bulleted
Question
Chapter 23.2, Problem 3P
Interpretation Introduction
Interpretation: The slow steps for the given acid catalyzed ester hydrolysis has to be predicted as specific-acid catalyzed or general-acid catalyzed.
Concept introduction:
Catalyst: Substance which helps in increasing the rate of a particular reaction without getting consumed in the reaction.
Acid Catalyst: A catalyst which helps in increasing the rate of a particular reaction by the donation of a proton. There are two types of catalysis:
- Specific-acid catalysis: Proton is completely transferred before the slow step to the reactant in a reaction
- General-acid catalysis: Proton is completely transferred during the slow step to the reactant in a reaction
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
In which step in the acid-catalyzed hydrolysis reaction mechanism of the ester is the direction of flow of electrons given incorrectly?
The final products for the hydroxide-ion-promoted hydrolysis of an ester re the carboxylate ion and methanol instead of the carboxylic acid and methoxide ion. Why?
What is the importance of proton transfer in the formation of ester?
A.The carbonyl carbon is easily attacked by the nucleophile.
B. The oxygen that has been attached to the two alkyl groups will become stable.
C. The removal of a bulky substituent attached to the reactive site stabilizes the compound.
D. none of the above
Chapter 23 Solutions
Organic Chemistry
Ch. 23.2 - Compare each of the mechanisms listed here with...Ch. 23.2 - Prob. 3PCh. 23.2 - Prob. 4PCh. 23.3 - a. Draw the mechanism for the following reaction...Ch. 23.5 - Prob. 7PCh. 23.5 - Propose a mechanism for the Co2+ catalyzed...Ch. 23.6 - Prob. 9PCh. 23.7 - Prob. 10PCh. 23.7 - Prob. 12PCh. 23.7 - Prob. 13P
Ch. 23.9 - Which of the following amino acid side chains can...Ch. 23.9 - Which of the following C-terminal peptide bonds is...Ch. 23.9 - Carboxypeptidase A has esterase activity as well...Ch. 23.9 - Arginine and lysine side chains fit into trypsins...Ch. 23.9 - Explain why serine proteases do not catalyze...Ch. 23.10 - If H2 18O is used in the hydrolysis reaction...Ch. 23.10 - When apples that have been cut are exposed to...Ch. 23.11 - Prob. 22PCh. 23.11 - The pHactivity profile for glucose-6-phosphate...Ch. 23.11 - Draw the pH-activity profile for an enzyme that...Ch. 23.12 - Prob. 25PCh. 23.12 - Draw the mechanism for the hydroxide ion-catalyzed...Ch. 23.12 - What advantage does the enzyme gain by forming an...Ch. 23.12 - Prob. 28PCh. 23.12 - Aldolase shows no activity if it is incubated with...Ch. 23 - Which of the following parameters would be...Ch. 23 - Prob. 30PCh. 23 - Prob. 31PCh. 23 - Prob. 32PCh. 23 - Indicate the type of catalysis that is occurring...Ch. 23 - The deuterium kinetic isotope effect (KH2O/KD2O)...Ch. 23 - Prob. 35PCh. 23 - Co2+ catalyzes the hydrolysis of the lactam shown...Ch. 23 - there are two kinds of aldolases. Class I...Ch. 23 - Prob. 38PCh. 23 - The hydrolysis of the ester shown here is...Ch. 23 - Prob. 40PCh. 23 - At pH = 12, the rate of hydrolysis of ester A is...Ch. 23 - 2-Acetoxycyclohexyl tosylate reacts with acetate...Ch. 23 - Proof that an imine was formed between aldolase...Ch. 23 - Prob. 44PCh. 23 - a. Explain why the alkyl halide shown here reacts...Ch. 23 - Triosephosphate isomerase (TIM) catalyzes the...
Knowledge Booster
Similar questions
- A strong acid is generally used to catalyze the Fischer esterification of carboxylic acids.What two steps in the reaction are accelerated by the presence of strong acid? What function does the acid play in each of these steps?arrow_forwardState three factors that cause the uncatalyzed hydrolysis of an ester to be a slow reaction.arrow_forwardWhen a molecule has two esters, it can react via an intramolecular Claisen condensation. This is called a Dieckmann condensation. what would be the products of the following reaction (hint: what is going to happen to the protecting group in dilute aqueous acid?).arrow_forward
- What is difference between the acetoacetic and malonic ester syntheses? Provide an example of each, including all intermediates..arrow_forwardWhat sequence of reactions would allow a conversion of an ester to an anhydride?arrow_forwardGive an example of an ester that is used to activate alcohols towards nucleophilic substitution and beta-elimination reactionsarrow_forward
- The formation of cyanohydrin from a ketone is an example of A. electrophilic addition B. nucleophilic addition C. nucleophilic substitution D. electrophilic substitution E. none of the abovearrow_forwardEarly chemists could envision three possible mechanisms for hydroxide-ion-promoted ester hydrolysis. Devise an experiment that would show which of the three is the actual mechanism. 1. a nucleophilic acyl substitution reaction 2. an SN2 reaction 3. an SN1 reactionarrow_forwardWhat is the reaction mechanism for formaldehyde and phenol under acidic conditions.arrow_forward
- Draw the starting reactant that would produce this hydrazone when treated with this reagent. Ignore inorganic byproducts. NH2OH, TsOHarrow_forwardPlease give the reactions of the following of its esterification reaction: 1. benzoic acid 2. acetic acid + benzyl alcoholarrow_forwardWhat alkyl bromide(s) should be used in the malonic ester synthesis of each of the following carboxylic acids? a. propanoic acid c. 3-phenylpropanoic acid b. 2-methylpropanoic acid d. 4-methylpentanoic acidarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning