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
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?
The hydrolysis of the ester shown here is catalyzed by morpholine. Explain how morpholine catalyzes the reaction.
The SN2 type reaction will end up with the
substitution
2903
the
at the reaction center of the
reaction.
903
182903
SEY
9037
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
- Complete each acid-base reaction and predict whether the position of equilibrium lies toward the left or toward the right. (a) CH3CCH+CH3CH2ONa+CH3CH3OH (b) CH3CCCH2CH2OH+Na+NH2NH3(l)arrow_forwarddescribe how steric and electronic effects influence the postion of equilibrium when the electrophilic center of an aldehyde or ketone is under nucleophilic attack.arrow_forwardOn the basis of the general mechanism for acid-catalyzed ester hydrolysis shown in Mechanism 20.2, write an analogous sequence of steps for the specific case of ethyl benzoate hydrolysis.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_forwardOrganic chemistry students Danny and Claire are both performing elimination reactions of the following alkyl iodide. Danny uses potassium tert-butoxide to promote the reaction while Claire uses water and high temperatures. One of their reactions has provided a single elimination isomer while the other has provided a mixture of elimination isomers. Ме K H20, heat Danny's Reaction H Claire's Reaction Ме a) Which student's reaction (Danny or Claire) has provided a single elimination isomer? b) Draw all the elimination isomers obtained from both students' reactions. c) Which of the dienes drawn (by you) in question 3b is the most stable? Circle that diene above.arrow_forwardplease,complete those following reactions.arrow_forward
- Out of acid chlorides (least stable), anhydrides, esters, and amides (most stable). True or false Acid chlorides would be the most reactive to hydrolysis and Amides would be the least reactivearrow_forwardplease, complete the following reactionarrow_forwardWhat is the product of a Grignard reaction? O A 2° or 3° amine with the nitrogen bound to the R group from the Grignard reagent. O A six-membered ring. O An ester that incorporates the R group from the Grignard reagent. O A 2° or 3° alcohol with the a carbon bound to the R group from the Grignard reagent. Question 5 How do you prepare a Grignard reagent? O React an organohalide with magnesium metal. O React a carbonyl-containing compound with an organohalide. O Mix an organohalide with mollen magneshum. O React a carbonyl containing compound with magnesiummetal.arrow_forward
- Which of the following functional groups will react faster and at lower conditions to a nucleophilic attack? (you can think of a nucleophilic attack by an amine). O a. Carboxylic Acid o b. Nitrile о с. Асyl Нalide d. Esterarrow_forwardIn a base catalyzed keto-enol tautomerization of an aldehyde the first step of the mechanism is removal of the proton from the alpha carbon. removal for a proton from the carbonyl carbon. protonation of the carbonyl carbon. protonation of the carbonyl oxygen.arrow_forwardShow how acid derivatives hydrolyze to carboxylic acids under either acidic or basicconditions. Explain why some acid derivatives (amides, for example) require muchstronger conditions for hydrolysis than other derivatives.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage LearningOrganic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning