Test Bank Jeffrey Elbert University of Northern Iowa INTRODUCTION TO ORGANIC CHEMISTRY Third Edition William Brown Beloit College Thomas Poon Claremont McKenna, Pitzer, and Scripps Colleges John Wiley & Sons, Inc To order books or for customer service call 1-800-CALL-WILEY (225-5945) Copyright © 2005 by John Wiley & Sons, Inc Excerpts from this work may be reproduced by instructors for distribution on a not-for-profit basis for testing or instructional purposes only to students enrolled in courses for which the textbook has been adopted Any other reproduction or translation of this work beyond that permitted by Sections 107 or 108 of the 1976 United States Copyright Act without the permission of the copyright owner is unlawful Requests for permission or further information should be addressed to the Permissions Department, John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030 ISBN 0-471-68692-1 Printed in the United States of America 10 Printed and bound by Malloy Lithographing, Inc CONTENTS CHAPTER CHAPTER 12 CHAPTER 24 CHAPTER 36 CHAPTER 48 CHAPTER 61 CHAPTER 75 CHAPTER 88 CHAPTER 100 CHAPTER 10 116 CHAPTER 11 130 CHAPTER 12 138 CHAPTER 13 148 CHAPTER 14 161 CHAPTER 15 176 CHAPTER 16 191 CHAPTER 17 207 CHAPTER 18 221 CHAPTER 19 235 CHAPTER 20 247 CHAPTER 21 258 CHAPTER 22 271 Chapter Covalent Bonding and Shapes of Molecules Multiple Choice Which is the electronic configuration that describes Mg2+? (Sec 1.2) a) 1s2, 2s2 b) 1s2, 2s2, 2p6 c) 1s2, 2s2, 2p6, 3s2 d) 1s2, 2s2, 2p6, 3s2, 3p6 Which is the electronic configuration that describes C? (Sec 1.2) a) 1s2, 2s2, 2p5 b) 1s2, 2s2, 2p6, 3s2 c) 1s2, 2s2, 2p2 d) 1s2, 2s2, 2p6 Which ion is described by the electronic configuration 1s22s22p63s23p2? (Sec 1.2) a) Mg+ b) Al+ c) Si+ d) P+ Which atom is described by the electron configuration 1s22s22p63s23p7? (Sec 1.2) a) S b) Se c) Cl d) Br Which atom is described by the Lewis structure A ? (Sec 1.2) a) C b) P c) Se d) I Which atom is described by the Lewis structure A ? (Sec 1.2) a) C b) P c) Se d) I Which molecules contain both covalent and ionic bonds? (Sec 1.3) CH3OH I Na2CO3 II NH4Cl III NaCl IV a) I, II b) II, IV c) I, II, IV d) II, III Chapter Covalent Bonding and Shapes of Molecules Arrange the bonds in increasing order of ionic character (least first) (Sec 1.3) C-C I Na-O II C-N III O-H IV C-O V a) III, I, IV, II, V b) V, III, I, II, IV c) I, III, V, IV, II d) I, III, II, IV, V Which Lewis structure is correct? (Sec 1.3) H H H a) H C OH b) H C C H H c) H O O H d) H :O : O C O 10 Which Lewis structures are correct? (Sec 1.3) H O O H H H H H N N H H N O I II a) b) c) d) H H C H H III IV Cl I, II II, IV III, IV I, III 11 Which molecules are polar? (Sec 1.5) NH3 CO2 H2O I II III a) b) c) d) I, IV I, III II, III, IV III, IV, V CH4 Br2 IV V H Chapter Covalent Bonding and Shapes of Molecules 12 Which molecules are polar? (Sec 1.5) O H2C CH2 I H C H II CH2Cl2 H3C CH3 CH3OH III IV V a) III, IV, V b) I, IV c) II, III, V d) I, III 13 Which functional groups have correct Lewis structures? (Sec 1.3) O C O H C O hydroxyl I carbonyl II C O H carboxyl III a) I, II b) II, III c) I, II, III d) I, III 14 Which is the correct Lewis structure for acetic acid (CH3CO2H)? (Sec 1.3) H O H O H C C O H H H C H C O H C O C H H a) O O H H H O C H b) H c) d) 15 Using the VSEPR model, predict which atoms have bond angles of about 120° (Sec 1.4) O H3C C H I CH3OH CH2 CH2 III II a) II, IV b) I, IV c) II, III d) I, III C NH4Cl IV H Chapter Covalent Bonding and Shapes of Molecules 16 According to VSEPR model, what is your prediction for the arrangement of electron pairs for CH3-? (Sec 1.4) a) linear b) tetrahedral c) bent d) trigonal 17 Using the VSEPR model, predict which species have bond angles of about 109° (Sec 1.4) NH3 CO2 H2O H3O I II III IV + O3 V a) I, III, IV b) II, III, V c) I, IV d) III, IV, V 18 What is the correct structure for the aldehyde which has the formula C4H8O? (Sec 1.3) OH a) CH3 O CH CH CH2 b) CH3 C CH2 d) H2C CH CH2 CH3 O c) CH3 CH2 CH2 CH O CH3 19 Nitrogen has a negative formal charge in which of the following compounds? (Sec 1.3) a) NaNH2 b) N2 c) NH4Cl d) HCN 20 What is the formal charge of oxygen in H3O+? (Sec 1.3) a) –1 b) c) +1 d) +2 21 What is the formal charge of indicated carbon in, NaC CH (Sec 1.3) a) –2 b) –1 c) d) +1 Chapter Covalent Bonding and Shapes of Molecules 22 The carbon has the correct orbital hybridization in which structures? (Sec 1.7) H2C H2C O CH2 CH4 sp2 II sp I HC N O C O sp IV sp V sp2 III a) II, IV, V b) II, III, IV c) I, II, III d) I, IV, V 23 What are the correct orbital hybridizations for carbon in the following species? (Sec 1.7) A CH3 I sp B CH4 II sp C CH III sp a) A and I, B and III b) B and I, C and II c) A and III, C and II d) B and III, C and III 24 Which of the following are pairs of contributing resonance structures? (Sec 1.6) I CH3 II III H2C IV O CH3 CH3 CH2 OH H2C O H2C O CH CH2 H2C CH CH2 N C O N C O a) II, IV b) I, II, III c) III, IV d) II, III, ,IV Chapter Covalent Bonding and Shapes of Molecules 25 Carbon has how many valence electrons? (Sec 1.2) a) b) c) d) 26 Oxygen has how many valence electrons? (Sec 1.2) a) b) c) d) 27 Nitrogen has how many valence electrons? (Sec 1.2) a) b) c) d) 28 Which statement about orbitals is false? (Sec 1.2) a) Orbitals are regions of space where electrons are found b) Orbitals may contain up to two electrons c) Orbitals are filled in order of decreasing energy d) Orbitals of equivalent energy are half filled before adding two electrons to any one of them 29 Which statement about resonance structures is false? (Sec 1.6) a) All contributing resonance structures must have the same number of valence electrons b) All contributing structures must obey the rules of covalent bonding c) The position of nuclei may change d) Third period atoms may have up to 12 electrons around them 30 Which functional groups are named correctly? (Sec 1.8) O H3C C O O H alcohol I CH3 OH aldehyde II H3C C H N CH3 CH3 ketone III a) III, IV, V b) II, III, IV c) I, III, V d) I, III, IV CH3 amine IV H3C C OH carboxylic acid V Chapter 21 Lipids T F F T F 10 T 270 Chapter 22 The Organic Chemistry of Metabolism Multiple Choice Which are oxidation / reduction reagents in the metabolism of fatty acids? (Sec 22.2, 22.6) I) ATP II) ADP III) NAD+ / NADH IV) FAD / FADH2 a) b) c) d) I, II III, IV I, III II, IV Which are agents for energy storage and transport? (Sec 22.2) I) ATP II) ADP III) NAD+ / NADH IV) FAD / FADH2 a) b) c) d) I, II III, IV I, III II, IV Which is the oxidizing agent for the following reaction? (Sec 22.6) O O CH2CH2CH2CSCoA CSCoA H C H3C a) b) c) d) C H FAD FADH2 NAD+ NADH 271 Chapter 22 The Organic Chemistry of Metabolism Which is the oxidizing agent for the following reaction? (Sec 22.6) OH O O CH3CHCH2CSCoA a) b) c) d) O CH3CCH2CSCoA FAD FADH2 NAD+ NADH Which is reagent X and product Y in this reaction? (Sec 22.6) O O X CH3CH2CCH2CSCoA a) b) c) d) O CH3CH2CSCoA + Y X= acetyl CoA, Y= coenzyme A X=coenzyme A, Y= acetyl CoA X= FAD, Y= FADH2 X= NAD+, Y= NADH The following are key steps in fatty acid metabolism What is the best description for the first step (A)? (Sec 22.6) O RCH CHCSCoA A OH O RCH CH2CSCoA O B O RC CH2CSCoA C O O RCSCoA + CH3CSCoA a) b) c) d) oxidation hydration reverse-Claisen condensation selective reduction 272 Chapter 22 The Organic Chemistry of Metabolism The following are key steps in fatty acid metabolism What is the best description for the first step (B)? (Sec 22.6) O RCH CHCSCoA A OH O RCH CH2CSCoA O B O RC CH2CSCoA C O O RCSCoA + CH3CSCoA a) b) c) d) oxidation hydration reverse-Claisen condensation selective reduction The following are key steps in fatty acid metabolism What is the best description for the first step (C)? (Sec 22.6) O RCH CHCSCoA A OH O RCH CH2CSCoA O B O RC CH2CSCoA C O O RCSCoA + CH3CSCoA a) b) c) d) oxidation hydration reverse-Claisen condensation selective reduction The biosynthesis of butanoic acid proceeds via a Claisen reaction of Acetyl-CoA If the starting material is labeled at the methyl carbon atom, which atoms will be labeled in the product? (Sec 22.6) O CH3CSCoA O CH3CH2CH2COH I a) b) c) d) II III IV I, II I, III II, III II, IV 273 Chapter 22 The Organic Chemistry of Metabolism 10 Which best describes this reaction? (Sec 22.6) O O CH3CH2CCH2CSCoA a) b) c) d) X O CH3CH2CSCoA + Y reverse aldol reaction aldol reaction reverse-Claisen condensation Claisen condensation 11 Unsaturated fatty acids require an additional enzyme in the metabolic pathway Which process involves this enzyme? (Sec 22.6) a) b) c) d) oxidation reduction enol / keto isomerization cis / trans isomerization 12 Which agent initially activates fatty acids for further reaction? (Sec 22.6) a) b) c) d) NAD+ FAD Coenzyme A + ATP ADP 13 Which statements describing β-oxidation of fatty acid are true? (Sec 22.6) I) More energy is released in the oxidation of fatty acids than sugars II) Only NAD+ / NADH are involved in the reactions III) The series of four reactions is repeated until the entire fatty acid chain is degraded to acetylCoA IV) The activated fatty acid is a carboxylic-diphosphoric mixed anhydride a) b) c) d) II, IV I, III II, III I, IV 14 Which statement is true concerning the balanced half reaction for the oxidation of glucose to pyruvate? (Sec 22.3, 22.4) a) b) c) d) The reaction produces two moles of oxygen The reaction is a four-electron oxidation The reaction uses two moles of NAD+ The reaction uses two moles of FAD 274 Chapter 22 The Organic Chemistry of Metabolism 15 Which reactions are involved in the conversion of pyruvate to ethanol? (Sec 22.5) I) oxidation II) reduction III) decarboxylation IV) keto-enol tautomerization a) b) c) d) I, III II, IV II, III III, IV 16 If carbon atom of glucose is labeled with 13C, which carbon atom is labeled after oxidation to pyruvate? (Sec 22.5) a) b) c) d) carbon atom carbon atom carbon atom carbon atoms and 17 Which describes Step of glycolysis, the cleavage of fructose 1,6-bisphosphate to two trioses? (Sec 22.4) a) b) c) d) Claisen condensation aldol addition reaction reverse-Claisen condensation reverse-Aldol reaction 18 How many moles of ethanol and CO2 are produced in the glycolysis and fermentation of sucrose? (Sec 22.5) a) b) c) d) moles ethanol, moles CO2 moles ethanol, moles CO2 moles ethanol, moles CO2 moles ethanol, moles CO2 19 If carbon of glucose is labeled with 13C, which carbon is labeled in the alcohol fermentation products? (Sec 22.5) a) b) c) d) CO2 ethanol carbon ethanol carbon ethanol carbon and carbon 20 Which describes the effect of lactate fermentation of glucose on blood pH and CO2 concentration? (Sec 22.5) a) b) c) d) pH increases, CO2 concentration increases pH decreases, CO2 concentration is unchanged pH is unchanged, CO2 concentration decreases pH decreases, CO2 concentration decreases 275 Chapter 22 The Organic Chemistry of Metabolism 21 If deuterium is substituted for hydrogen in NADH, where will the deuterium be in the final product of the metabolic reduction of pyruvate to lactate? (Sec 22.5) I H3C II OH C CO H O III a) b) c) d) I II III II, III 22 If palmitic acid is labeled at carbon with 13C, which carbon will be labeled in acetyl-CoA after β-oxidation? (Sec 22.6) a) b) c) d) the methyl carbon the carbonyl carbon both carbons neither carbon 23 Which reagents are necessary in the glycolysis of glucose to pyruvate? (Sec 22.4) I) NAD+ II) ADP III) HPO42IV) FAD V) ATP a) b) c) d) I, II, III, V II, III, IV, V I, III, V III, IV, V 24 How many steps are there in the glycolysis pathway? (Sec 22.4) a) b) c) d) 10 25 How many steps are there in the fatty acid β-oxidation pathway? (Sec 22.6) a) b) c) d) 10 276 Chapter 22 The Organic Chemistry of Metabolism 26 Which is the key intermediate in the enzyme catalyzed reverse-aldol reaction of fructose 1,6-bisphosphate to two trioses? (Sec 22.6) a) b) c) d) an amine an aldehyde an imine an amide 27 Which statements about carbohydrate digestion and absorption are true? (Sec 22.3, 22.4) I) The main function of carbohydrates is as a carbon source II) Hydrolysis begins in the mouth with α-amylase in saliva III) Starch is hydrolyzed directly to glucose IV) Hydrolysis is completed in the small intestine a) b) c) d) I, III II, IV I, IV II, III Fill in the Blank Complete the structure of Nicotinamide adenine dinucleotide (NAD) (Sec 22.2) O O P O CH2 O O OH NH2 OH N O P O CH2 O OH N O N N OH 277 Chapter 22 The Organic Chemistry of Metabolism Complete the following reaction mechanism by providing the correct mechanism arrows (Sec 22.2) -:Base-Enzyme H-Base-Enzyme H O O C C H H O H H NH2 O NH2 + N N Ad Ad Provide the product of the following reaction (Sec 22.2) H H HOOC R H + FAD + FADH2 H Provide the product of the following reaction (Sec 22.4) HOCH2 HO O + ATP HO OH hexokinase + ADP Mg2+ OH Provide the products of the following reaction (Sec 22.4) 2- CH2OPO3 O HO H H OH H OH aldolase + 2CH2OPO3 278 Chapter 22 The Organic Chemistry of Metabolism Provide the product of the following reaction (Sec 22.4) 2- CH2OPO3 O HO H H OH H OH + H3N-Enzyme-Base: 2- CH2OPO3 Provide the product of the following reaction (Sec 22.5) O H 3C C COO - lactate + NADH + H3O+ + NAD+ + H3O+ dehydrogenase Provide the product of the following reaction (Sec 22.6) O O R C CH2 C O SCoA + thiolase-S- R C S-Enzyme + Provide the product of the following reaction (Sec 22.6) -OOC O - O CH2 C COO + H3C C citrate SCoA + H2O + CoA-SH synthase 10 Provide the product of the following reaction (Sec 22.7) COO COO- H2C COO H C O C + H+ + CO2 279 Chapter 22 The Organic Chemistry of Metabolism True-False The citric acid cycle is the main metabolic pathway under anaerobic conditions (Sec 22.7) The following structure is ADP (Sec 22.2) O N HN P O H2N H2 P O C O O O O O N N O OH OH The following reaction is a reduction of the alcohol, oxidation of NAD= (Sec 22.2) OH O C + NAD+ C H The following structure is FAD (Sec 22.2) O N NH N N H H H OH H OH H OH NH2 O P O O N N CH2 O O O H 2N P O CH2 N O OH N O OH 280 + NADH + H+ Chapter 22 The Organic Chemistry of Metabolism FAD is reduced in the following reaction (Sec 22.2) CH2 CH2 + FAD CH CH + FADH2 Acetyl-CoA is derived from the degradation of foodstuffs (Sec 22.6) The cleavage of fructose-1,6-bisphosphate to two triose phosphates (reaction of the glycolysis sequence) is an example of an aldol reaction (Sec 22.6) Pyruvate is the conjugate base of a β-keto carboxylic acid (Sec 22.5) O H3C C COO - Cleavage of the β-ketoacyl-CoA in reaction of the β-oxidation of fatty acids is an example of a retro-Claisen condensation (Sec 22.6) 10 The citric acid cycle oxidizes acetyl-CoA to CO2, producing NADH and FADH2 (Sec 22.7) 281 Chapter 22 The Organic Chemistry of Metabolism Answers Multiple Choice b a a c b b a c b 10 c 11 d 12 c 13 b 14 b 15 c 16 a 17 d 18 d 19 c 20 b 21 c 22 a 23 a 24 d 25 a 26 c 27 b Fill in the Blank O NH2 O O P O CH2 N O O OH NH2 OH N O P O CH2 O OH N O N N OH 282 Chapter 22 The Organic Chemistry of Metabolism -:Base-Enzyme H-Base-Enzyme H O O C C H H O H H NH2 NH2 + N N Ad Ad H R HOOC H 2- O POH C O HO HO OH OH 2CH2OPO3 O + H O H OH CH2OH 2- CH2OPO3 2CH2OPO3 N-Enzyme-Base: - HO H H OH H OH O 2CH2OPO3 283 Chapter 22 The Organic Chemistry of Metabolism OH H3C C COO - H O H3C C SCoA H 2C HO C H 2C COO COOCOO 10 H2C COO - CH2 O C COO- True-False F F F T T T F F T 10 T 284