Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 29.SE, Problem 55AP
In step 7 of fatty-acid biosynthesis (Figure 29-5), dehydration of a β-hydroxy thioester occurs to give trans-crotonyl ACP. Is the dehydration a syn elimination or an anti elimination?
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PRODUCTS. Match the name of the product with the biochemical reaction. Products may be used more than once. Tests may require more than one answer.a. 2,3-butanediol 1.catalase b. ammonia 2.phenylalanine deamination c.fatty acids 3.triglyceride hydrolysis d. indole 4.tryptophan degradation e.molecular oxygen 5.urea hydrolysis f. phenylpyruvic acid 6.Voges-Proskauer test
Chapter 29 Solutions
Organic Chemistry
Ch. 29.1 - Prob. 1PCh. 29.3 - Write the equations for the remaining passages of...Ch. 29.3 - Prob. 3PCh. 29.4 - Write a mechanism for the dehydration reaction of...Ch. 29.4 - Evidence for the role of acetate in fatty-acid...Ch. 29.4 - Does the reduction of acetoacetyl ACP in step 6...Ch. 29.5 - Prob. 7PCh. 29.5 - Look at the entire glycolysis pathway, and make a...Ch. 29.6 - Prob. 9PCh. 29.7 - Prob. 10P
Ch. 29.7 - Write mechanisms for step 2 of the citric acid...Ch. 29.7 - Prob. 12PCh. 29.8 - Prob. 13PCh. 29.9 - Write all the steps in the transamination reaction...Ch. 29.9 - What -keto acid is formed on transamination of...Ch. 29.9 - Prob. 16PCh. 29.SE - Prob. 17VCCh. 29.SE - Identify the following intermediate in the citric...Ch. 29.SE - The following compound is an intermediate in the...Ch. 29.SE - Prob. 20VCCh. 29.SE - In the pentose phosphate pathway for degrading...Ch. 29.SE - Prob. 22MPCh. 29.SE - One of the steps in the pentose phosphate pathway...Ch. 29.SE - One of the steps in the pentose phosphate pathway...Ch. 29.SE - Prob. 25MPCh. 29.SE - Prob. 26MPCh. 29.SE - Prob. 27MPCh. 29.SE - Prob. 28MPCh. 29.SE - Prob. 29MPCh. 29.SE - Prob. 30MPCh. 29.SE - Prob. 31MPCh. 29.SE - Prob. 32APCh. 29.SE - Prob. 33APCh. 29.SE - Prob. 34APCh. 29.SE - Prob. 35APCh. 29.SE - Prob. 36APCh. 29.SE - Prob. 37APCh. 29.SE - Prob. 38APCh. 29.SE - Prob. 39APCh. 29.SE - Prob. 40APCh. 29.SE - Prob. 41APCh. 29.SE - Prob. 42APCh. 29.SE - Prob. 43APCh. 29.SE - Prob. 44APCh. 29.SE - Prob. 45APCh. 29.SE - Prob. 46APCh. 29.SE - Prob. 47APCh. 29.SE - Prob. 48APCh. 29.SE - Prob. 49APCh. 29.SE - Prob. 50APCh. 29.SE - In glycerol metabolism, the oxidation of...Ch. 29.SE - Prob. 52APCh. 29.SE - Prob. 53APCh. 29.SE - Prob. 54APCh. 29.SE - In step 7 of fatty-acid biosynthesis (Figure...Ch. 29.SE - Prob. 56AP
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- Assume that acetyl CoA containing a 14C isotopic label in the carboxyl carbon atom is used as starting material for the biosynthesis of mevalonate, as shown in Figure 27-7. At what positions in mevalonate would the isotopic label appear?arrow_forwardWhat product would you obtain by reduction of digitoxigenin (Problem 27-39) with LiAlH4? By oxidation with the Dess–Martin periodinane?arrow_forwardEvidence for the role of acetate in fatty-acid biosynthesis comes from isotopelabeling experiments. If acetate labeled with 13C in the methyl group (13CH3CO2H) were incorporated into fatty acids, at what positions in the fattyacid chain would you expect the 13C label to appear?arrow_forward
- Propose a mechanism for the cyclization of the ketodiol from Step 8 to frontalin.arrow_forwardDraw the products that form when the thioester CH3CH2CH2COSCoA is hydrolyzed with water. Differentiate products by greater or lesser molecular weight.arrow_forwardA 2-ketohexose is reduced with NaBH4 in CH3OH to form a mixture of D-galactitol and Dtalitol. What is the structure of the 2-ketohexose?arrow_forward
- What is the mech for an acid catalyzed keto-enol interconversion?arrow_forwardAssume that acetyl CoA containing a 14C isotopic label in the carboxyl carbon atom is used as starting material and that the mevalonate pathway is followed. Identify the positions in lanosterol where the label would appear.arrow_forwardOne of the steps in the pentose phosphate pathway for glucose catabolism is the reaction of xylulose 5-phosphate with ribose 5-phosphate in the presence of a transketolase to give glyceraldehyde 3-phosphate and sedoheptulose 7-phosphate. (a) The first part of the reaction is nucleophilic addition of thiamin diphosphate (TPP) ylide to xylulose 5-phosphate, followed by a retro-aldol cleavage to give glyceraldehyde 3-phosphate and a TPPcontaining enamine. Show the structure of the enamine and the mechanism by which it is formed. (b) The second part of the reaction is addition of the enamine to ribose 5-phosphate followed by loss of TPP ylide to give sedoheptulose 7-phosphate. Show the mechanism.arrow_forward
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