Organic Chemistry, 8e (Bruice) Module 8 Practice Test 1 Copyright © 2017 Pearson Education, Inc. Chapter 20 The Organic Chemistry of Carbohydrates 1. Which of the following represents the general...

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Organic Chemistry, 8e (Bruice) Module 8 Practice Test 1 Copyright © 2017 Pearson Education, Inc. Chapter 20 The Organic Chemistry of Carbohydrates 1. Which of the following represents the general formula of a carbohydrate? Section: 20-0 A) CnH2n+2 B) CnH2n C) CnH2n-2 D) Cn(H2O)n E) Cn(HO)n 2. Which of the following best represents the process of photosynthesis? Section: 20-0 A) disproportionation B) oxidation/reduction C) exothermic D) exergonic E) elimination 3. A carbohydrate composed of three to ten sugar molecules is called a(n) A) single carbohydrate. B) disaccharide. C) oligosaccharide. D) polysaccharide. E) monosaccharide. Section: 20-1 4. Which of the following compounds is a D-sugar? Section: 20-2 A) B) C) D) E) 5. All chiral D-sugars rotate plane-polarized light Section: 20-2 A) clockwise. B) counterclockwise. C) +20.0°. D) in a direction that cannot be predicted but must be determined experimentally. E) since they are optically inactive. 6. Is the following structure of glucose a D or L configuration? Explain. Section: 20-2 7. Epimers are essentially Section: 20-3 A) enantiomers. B) diasteromers. C) identical. D) constitutional isomes. E) tautomers. 8. Which of the following corresponds to the definition of an aldopentose? Section: 20-3 I. It is a monosaccharide. II. It contains a CHO group III. It is a disaccharide. IV. It is an oligosaccharide. A) I and II B) II and III C) I and IV D) I and III E) I, II, and III Module 8 Practice Test 2 Copyright © 2017 Pearson Education, Inc. 9. Is L-glucose the enantiomer of D-glucose, the C-5 epimer of D-glucose, or both? Section: 20-3 10. What is the relationship between the following compounds? Section: 20-3 A) conformational isomers B) constitutional isomers C) identical D) enantiomers E) diastereomers 11. At which carbon are the following sugars epimers of each other? Section: 20-3 A) C-1 B) C-2 C) C-3 D) C-4 E) C-5 12. At which carbon are the following sugars epimers of each other? Section: 20-3 A) C-1 B) C-2 C) C-3 D) C-4 E) C-5 13. How many chirality centers are there in an aldohexose? Section: 20-3 A) 2 B) 3 C) 4 D) 5 E) 6 Module 8 Practice Test 3 Copyright © 2017 Pearson Education, Inc. 14. Assign the proper configurational descriptor to each asymmetric center (R or S) in D-glucose below. Section: 20-3 15. The open-chain form of D-idose is shown below. Draw the open-chain form of the C-3 epimer of D-idose. Section: 20-3 16. Fructose is described as a(n) Section: 20-4 A) aldopentose. B) ketopentose. C) aldohexose. D) ketohexose. E) none of the above. 17. At which carbon are the following sugars epimers of each other? Section: 20-4 A) C-1 B) C-2 C) C-3 D) C-4 E) C-5 18. How many chirality centers are there in a 2-ketohexose? Section: 20-4 A) 2 B) 3 C) 4 D) 5 E) 6 19. How many stereoisomers are possible for a 2-ketohexose? Section: 20-4 A) 2 B) 4 C) 8 D) 16 E) 32 Module 8 Practice Test 4 Copyright © 2017 Pearson Education, Inc. 20. Draw the enolate of D-glucose. Section: 20-5 21. What is epimerization? Section: 20-5 A) involves changing the configuration of a carbon of a monosaccharide through deprotonation followed by reprotonation B) involves oxidation of an aldose C) involves lengthening the chain of an aldose D) involves reduction of an aldose E) none of the above 22. When D-threose is treated with NaBH4 Section: 20-6 A) a 70:30 mixture of enantiomeric alditols results. B) a 50:50 mixture of enantiomeric alditols results. C) a meso alditol is produced. D) the product mixture contains two diastereomeric alditols. E) an optically active alditol is produced. 23. Which of the following sugars yields the same alditol upon reduction with NaBH4 as does D-glucose? Section: 20-6 A) D-fructose B) D-mannose C) L-glucose D) D-arabinose E) none of the above 24. Reduction of a 2-ketohexose with NaBH4 yields Section: 20-6 A) a single aldohexose. B) a mixture of acetals. C) a mixture of alditols. D) a mixture of cyclic hemiacetals. E) a single pyranose. 25. Which of the following is/are the product(s) obtained from the reduction of D-fructose? Section: 20-6 A) B) C) D) A and B E) A and C 26. Provide the Fischer projection of the open-chain form of the aldonic acid which results when L-glucose is treated with bromine water. Section: 20-6 Module 8 Practice Test 5 Copyright © 2017 Pearson Education, Inc. 27. Which of the following monosaccharides will form D-glucaric acid (shown below) upon oxidation with nitric acid? Section: 20-6 A) B) C) D) A and B E) A and C 28. When D-sorbose (shown below) is treated with NaBH4, which of the following is produced? Section: 20-6 A) a single optically active alditol B) a single optically inactive alditol C) a racemic mixture of alditols D) an optically inactive mixture of epimeric alditols E) an optically active mixture of epimeric alditols 29. Provide the structure of the product which results when D-ribose is treated with bromine water. Section: 20-6 Module 8 Practice Test 6 Copyright © 2017 Pearson Education, Inc. 30. When D-tagatose is added to a basic aqueous solution, an equilibrium mixture of three monosaccharides is obtained. Identify the monosaccharides. Section: 20-6 31. Provide the major organic product(s) of the reaction below. Section: 20-6 A) B) 32. Give the major product(s) for the reaction. You may choose more than one answer. Section: 20-6 A) B) C) D) E) Module 8 Practice Test 7 Copyright © 2017 Pearson Education, Inc. 33. Give the major product(s) for the reaction. Section: 20-6 A) B) C) D) E)