Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Question
Chapter 13, Problem 48P
Interpretation Introduction
Interpretation: Reason behind the formation of acetone containing
Concept introduction: Decarboxylation of acetoacetate is initiated by an enzyme named acetoacetate decarboxylase. Enzyme forms protonate imine with substrate acetoacetate. It loses carbondioxide in presence of a
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Acetylcholine esterase is an important enzyme in neural synaptic signal transmission.
It breaks down the neurotransmitter acetylcholine after it binds the acetylcholine
receptor. Its active site has the same features used by serine proteases.
Here is the reaction catalyzed by Acetylcholine esterase:
Acetylcholine
Choline
OH
Acetate
+ H
Acetylcholine is an ester, while peptide bonds cleaved by proteases are amides. How
should acetylcholine estease's mechanism accommodate this?
This cannot be determined from the information presented in class and in this
question.
For amides, the amide nitrogen is deprotonate to make it more like an ester. The
same mechanism cleaves deprotonated amides and esters.
No changes are needed. The mechanism same works for esters and amides.
Prior to cleavage, a transamination converts the ester to an amide.
The esterase will make a covalent intermediate to an amine to create the amide
to be cleaved.
A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. Is the product capable of showing optical activity? If it is, explain how.
A graduate student was studying enzymatic reductions of cyclohexanones when she encountered some interesting chemistry. When she used an enzyme and NADPH to reduce the following ketone, she was surprised to find that the product was optically active. She carefully repurified the product so that no enzyme, NADPH, or other contaminants were present. Still, the product was optically active. If this reaction could be accomplished using H2 and a nickel catalyst, would the product be optically active? Explain.
Chapter 13 Solutions
Essential Organic Chemistry, Global Edition
Ch. 13.1 - Identify the most acidic hydrogen in each...Ch. 13.1 - Prob. 2PCh. 13.1 - Prob. 3PCh. 13.1 - Prob. 4PCh. 13.1 - Explain why HO cannot remove a proton from the...Ch. 13.2 - Prob. 6PCh. 13.2 - Prob. 7PCh. 13.3 - Prob. 8PCh. 13.3 - Prob. 9PCh. 13.3 - Prob. 10P
Ch. 13.4 - Prob. 11PCh. 13.5 - Prob. 12PCh. 13.5 - Prob. 13PCh. 13.6 - Prob. 14PCh. 13.7 - Prob. 16PCh. 13.8 - Prob. 17PCh. 13.8 - Prob. 18PCh. 13.8 - Prob. 19PCh. 13.9 - Prob. 20PCh. 13.10 - Propose a mechanism for the formation of...Ch. 13.10 - Prob. 22PCh. 13.10 - a. If the biosynthesis of palmitic acid were...Ch. 13 - Draw the enol tautomers for each of the following...Ch. 13 - Number the following compounds in order from...Ch. 13 - Prob. 26PCh. 13 - Explain why the pKa of a hydrogen bonded to the...Ch. 13 - Prob. 28PCh. 13 - Prob. 29PCh. 13 - Prob. 30PCh. 13 - Prob. 31PCh. 13 - Prob. 32PCh. 13 - Prob. 33PCh. 13 - Using cyclopentanone as the reactant, show the...Ch. 13 - Prob. 35PCh. 13 - Prob. 36PCh. 13 - Prob. 37PCh. 13 - Prob. 38PCh. 13 - Prob. 39PCh. 13 - Prob. 40PCh. 13 - Prob. 41PCh. 13 - Prob. 42PCh. 13 - Prob. 43PCh. 13 - Prob. 44PCh. 13 - Describe how the following compounds can be...Ch. 13 - Prob. 46PCh. 13 - Which would require a higher temperature:...Ch. 13 - Prob. 48PCh. 13 - Propose a mechanism for the following reaction:Ch. 13 - Show how the following compounds could be...Ch. 13 - Prob. 51PCh. 13 - Prob. 52P
Knowledge Booster
Similar questions
- Describe a reaction mechanism that occurs to maleic acid when hydrochloric acid is added.arrow_forwardComplete the following reaction sequence, giving structural details of all key intermediates:arrow_forwardMany multi-step organic reaction mechanisms involve proton transfer steps. For example, the first step of Fischer esterification of carboxylic acids(as shown with acedic acid) is activation of the acid by protonation. Based on your understanding of which reaction pathway is more favorable, explain why using chemical structures.arrow_forward
- An elevated level of the enzyme alkaline phosphatase (ALP) in human serum is an indication of possible liver or bone disorder. The level of serum ALP is so low that it is very difficult to measure directly. However. ALP catalyzes a number of reactions, and its relative concentration can be determined by measuring the rate of one of these reactions under controlled conditions. One such reaction is the conversion of p-nitrophenyI phosphate (PNPP) to p-nitrophenoxide ion (PNP) and phosphate ion. Control of temperature during the test is very important; the rate of the reaction increases 1.47 times if the temperature changes from 30 C to 37 C. What is the activation energy for the ALP-catalyzed conversion of PNPP to PNP and phosphate?arrow_forwardUnder acidic conditions (such as in your stomach) benzyl penicillin (BP) breaks down to three products which we will call A, B, and C in a parallel reaction with the following A BP B. values for the rate constants: ka = 7.0 × 10-4 sec-1; ks = 4.1 x 10-3 sec-1; and ke 5.7 x 10-3 sec-1. What is the yield of product A? In other words, after the reaction has reached completion what fraction of the product is present as compound-A?arrow_forwardWhich of the following can form a carbinolamine intermediate with ammonia? a Bromoethane b Ethyl nitrile c Acetaldehyde d Ethanaminearrow_forward
- What is the rate of reaction of Na2SO4 ?arrow_forwardWhen the ammonium salt (CH3CH2CH2)3NHCl is treated with NaOH, the products are water, NaCl, and an organic product. Provide the product in an attached file.arrow_forwardWrite the reactions and reactants benzoic acid chloride to benzoic anhydride benzoic anhydride to ethyl benzamide Write the reaction mechanism for the second reactionarrow_forward
- In 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_forwardProline betaine is a putative osmoprotectant in plants and bacteria, helping to prevent dehydration of cells. Coo- CH, CH, Propose a plausible pathway for biosynthesis of this compound.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_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
- Chemistry by OpenStax (2015-05-04)ChemistryISBN:9781938168390Author:Klaus Theopold, Richard H Langley, Paul Flowers, William R. Robinson, Mark BlaserPublisher:OpenStax
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT
Chemistry by OpenStax (2015-05-04)
Chemistry
ISBN:9781938168390
Author:Klaus Theopold, Richard H Langley, Paul Flowers, William R. Robinson, Mark Blaser
Publisher:OpenStax