Organic Chemistry
6th Edition
ISBN: 9781936221349
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
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Chapter 24, Problem 24.24P
Interpretation Introduction
Interpretation:
An explanation as to why the methyl
Concept introduction:
Oxidation is a type of reaction in which addition of oxygen atom or removal of hydrogen atom takes place. It occurs by the loss of electrons. The substance which gets reduced in a reaction is called the oxidizing agent. Oxidizing agent is the substance that causes oxidation in
The periodate (an anion composed of iodine and oxygen) is an oxidizing agent.
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The most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial
position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the a or B anomer
of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.
How many chiral centers are in B-d-glucopyranose and a-D-galactopyranose? How many stereoisomers of these two aldohexoses can theoretically be drawn?
One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate,
reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH.
-OPO3²- Enz-SH
H-C-OH
ATP
CH₂OPO3²-
3-phosphoglycerate
O
0-0--0
O
ADP
CH₂CH3
substitute for
1,3-bisphosphoglycerate
C
H-C-OH
CH₂OPO3²-
1,3-bisphosphoglycerate
O=C
CH3-SH
substitute for
Enz-SH
H
H-C-OH
|
CH₂OPO3²-
PO4³-
O.
S-Enz
H-C-OH
glyceraldehyde 3-phosphate
Propose a structure for the first intermediates in the reaction of 1,3-bisphosphoglycerate with a thiol group on the enzyme to form an enzyme-bound thioester. Assume a basic group on the enzyme catalyzes the formation of this
intermediate.
To simplify the drawing process, substitute the structures below for the 1,3-bisphosphoglycerate and Enz-SH.
CH₂OPO3²-
(Enzyme-bound
thioester)
NADH/H*
NAD*,…
Chapter 24 Solutions
Organic Chemistry
Ch. 24 - Prob. 24.1PCh. 24 - Prob. 24.2PCh. 24 - Prob. 24.3PCh. 24 - Prob. 24.4PCh. 24 - Prob. 24.5PCh. 24 - Prob. 24.6PCh. 24 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Prob. 24.15PCh. 24 - Prob. 24.16PCh. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 - Prob. 24.19PCh. 24 - Prob. 24.20PCh. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Prob. 24.24PCh. 24 - Prob. 24.25PCh. 24 - Prob. 24.26PCh. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - Prob. 24.34APCh. 24 - Prob. 24.35APCh. 24 - Prob. 24.36APCh. 24 - Prob. 24.37APCh. 24 - Prob. 24.38APCh. 24 - Prob. 24.39APCh. 24 - Prob. 24.40APCh. 24 - Prob. 24.41APCh. 24 - Prob. 24.42APCh. 24 - Prob. 24.43APCh. 24 - Prob. 24.44APCh. 24 - Prob. 24.45APCh. 24 - Prob. 24.46APCh. 24 - Prob. 24.47APCh. 24 - Prob. 24.49APCh. 24 - Prob. 24.50APCh. 24 - Prob. 24.51APCh. 24 - Prob. 24.52APCh. 24 - Prob. 24.53APCh. 24 - Prob. 24.54APCh. 24 - Prob. 24.55APCh. 24 - Prob. 24.56APCh. 24 - Prob. 24.57APCh. 24 - Prob. 24.58APCh. 24 - Prob. 24.59APCh. 24 - Prob. 24.60APCh. 24 - Prob. 24.61APCh. 24 - Prob. 24.62AP
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- Explain why methyl trifluoroacetate, CF3CO2CH3, is more reactive than methyl acetate, CH3CO2CH3, in nucleophilic acyl substitution reactions.arrow_forwardThe formyl of an aldose is converted to which functional group when oxidized? alkoxide carbonyl carboxyl hydroxylarrow_forwardThe most stable conformation of most aldopyranoses is one in which the largest group, the CH2OH group, is equatorial. However, alpha-D-idopyranose exists primarily in a conformation with an axial CH2OH group. Write formulas for the two chair conformations of a-D-idopyranose (one with the CH2OH group axial and one with the CH2OH group equatorial) and provide an explanationarrow_forward
- rivatives: Nucleophilic Acyl Substitution Reactions - EOC O C-O [References] One step in the gluconeogenesis pathway for the biosynthesis of glucose is the partial reduction of 3-phosphoglycerate to give glyceraldehyde 3-phosphate. The process occurs by phosphorylation with ATP to give 1,3-bisphosphoglycerate, reaction with a thiol group on the enzyme to give an enzyme-bound thioester, and reduction with NADH. H-C-OH ATP ADP CH₂OPO32- 3-phosphoglycerate 0= OPO32- C H-C-OH CH₂OPO32 1,3-bisphosphoglycerate Enz-SH PO43- O= C S-Enz H-C-OH CH₂OPO3² (Enzyme-bound thioester) NADH/H+ O=C NAD*, Enz-SH H H-C-OH CH₂OPO3²- glyceraldehyde 3-phosphate Propose a structure for the first intermediate in the reaction of the enzyme-bound thioester with NADH to form glyceraldehyde 3-phosphate. To simplify the drawing process, substitute the structure below for the enzyme-bound thioester. S-CH3 substitute for the CH2CH3 enzyme-bound thioester You do not have to consider stereochemistry. • You do not have…arrow_forwardDraw the Fischer projection of each pair of compound. Identify the term that best describes both compounds using any of the following choices namely: Aldoses, ketoses, trioses, or aldohexoses.arrow_forwardThe formyl of an aldose is converted to which functional group when oxidized? alkoxide carbonyl O hydroxyl carboxylarrow_forward
- chlorocyopentane may be synthesised in two different ways. fill in the missing reactant required for each pathwayarrow_forwardThe cyclic hemiacetal is more stable than the open-chain form, so very little of the open-chain form is present atequilibrium. Will an aqueous solution of glucose reduce Tollens reagent and give a positive Tollens test? Explain.arrow_forwardThe most stable conformation of the pyranose ring of most D-aldohexoses places the largest group, CH2OH, in the equatorial position. An exception to this is the aldohexose D-idose. Draw the two possible chair conformations of either the α or β anomer of D-idose. Explain why the more stable conformation has the CH2OH group in the axial position.arrow_forward
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