Organic Chemistry (8th Edition)
8th Edition
ISBN: 9780134042282
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 23.5, Problem 18P
Propose a mechanism for the α,β-elimination reaction shown on page 1082.
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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.
Draw the product of the following enzyme-catalysed recation given below
There are two kinds of aldolases. Class I aldolases are found in animals and plants, whereas class II aldolases are found in fungi, algae, and some bacteria. Only class I aldolases form an imine. Class II aldolases have a metal ion (Zn2+) at the active site. Propose a mechanism for catalysis by class II aldolases.
Chapter 23 Solutions
Organic Chemistry (8th Edition)
Ch. 23.1 - Prob. 2PCh. 23.1 - Prob. 3PCh. 23.2 - How many conjugated double bonds are there in a....Ch. 23.2 - Instead of adding to the 4a position and...Ch. 23.2 - Prob. 7PCh. 23.3 - Prob. 8PCh. 23.3 - Acetolactate synthase is another TPP-requiring...Ch. 23.3 - Acetolactate synthase transfers the acyl group of...Ch. 23.3 - Prob. 12PCh. 23.5 - Which compound is more easily decarboxylated?
Ch. 23.5 - Prob. 14PCh. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - Explain why the ability of PLP to catalyze an...Ch. 23.5 - The enzyme that catalyzes the C C bond cleavage...Ch. 23.5 - Propose a mechanism for the ,-elimination reaction...Ch. 23.6 - Ethanolamine ammonia lyase, a coenzyme...Ch. 23.6 - Prob. 20PCh. 23.7 - How do the structure of tetrahydrofolate and...Ch. 23.7 - What is the source of the methyl group in...Ch. 23.8 - Thiols such as ethanethiol and propanethiol can be...Ch. 23 - How does the metal ion in carboxypeptidase A...Ch. 23 - Prob. 24PCh. 23 - Prob. 25PCh. 23 - For each of the following reactions, name both the...Ch. 23 - Prob. 27PCh. 23 - When transaminated, the three branched-chain amino...Ch. 23 - What acyl groups have we seen transferred by...Ch. 23 - Propose a mechanism for the following reaction:Ch. 23 - Draw the products of the following reaction, where...Ch. 23 - When UMP is dissolved in T2O, exchange of T for H...Ch. 23 - Dehydratase is a PLP-requiring enzyme that...Ch. 23 - In addition to the reaction mentioned in Section...Ch. 23 - PLP can catalyze both ,-elimination reactions...Ch. 23 - The glycine cleavage system is a group of four...Ch. 23 - Prob. 37PCh. 23 - FADH2 reduces , -unsaturated thioesters to...
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- Draw the products of the diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + Δarrow_forwardDraw the products of the following hydrolysis. Н CH2 "CHз О—Н Нзс Нarrow_forwardExplain why α-pyrone reacts with Br2 to yield a substitution product (like benzene does), rather than an addition product to one of its C–C bonds.arrow_forward
- A generic ester is shown. What happens in a transesterification reaction? R —С—0—R In a transesterification, reaction with ROH replaces the OR, group with the OR. reaction with ROH replaces the R, group with the OR. reaction with ROH replaces both the R, group and the OR, group with the OR. reaction with ROH replaces the carbonyl group with the OR,arrow_forward8) Propose a multi-step synthesis pathway that utilize the indicated substrates to synthesize the following products. SHarrow_forwardThe product of this reaction is a(n): H3CO OCH 3 cyanohydrin ketone aldehyde imine ester H3O+ productarrow_forward
- Rank in order of increasing rate of hydrolysis (slowest to fastest). To preview the image click here e :0: :0: ⒸCarrow_forwardDraw a mechanism for the conversion of glucose from its aldehyde form to its hemiacetal form and then to its methyl glycoside (acetal) form under acidic conditions. Show all bond breaking and bond forming steps; show all intermediates.arrow_forwardA 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.arrow_forwardPropose a synthesis pathway to form the products.arrow_forwardAn α, β-unsaturated carbonyl compound can be prepared by a reaction known as a selenenylation–oxidation reaction. A selenoxide is formed as anintermediate. Propose a mechanism for the reaction.arrow_forwardThere are two kinds of aldolases. Class I aldolases are found in animals and plants, whereas class II aldolases are found in fungi, algae, and some bacteria.Only class I aldolases form an imine. Class II aldolases have a metal ion (Zn2 + ) at the active site. The mechanism for catalysis by class I aldolases wasdescribed in Section 22.13. Propose a mechanism for catalysis by class II aldolases.arrow_forwardarrow_back_iosSEE MORE QUESTIONSarrow_forward_ios
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