Organic Chemistry 1st Edition

Chapter 1 Electrons, Bonds and Molecular Properties Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 1. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary.

Chapter 10 Alkynes Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 10. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. A triple bond

Chapter 11 Radical Reactions Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 11. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. Radical mechanisms

Chapter 12 Synthesis Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 12. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. The position

Chapter 13 Alcohols Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 13. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. When naming an

Chapter 14 Ethers and Epoxides; Thiols and Sulfides Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 14. Each of the sentences below appears verbatim in the section entitled Review of Concepts

Chapter 15 Infrared Spectroscopy and Mass Spectrometry Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 15. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary.

Chapter 16 Nuclear Magnetic Resonance Spectroscopy Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 16. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. A spinning

Chapter 17 Conjugated Pi Systems and Pericyclic Reactions Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 17. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary.

Chapter 18 Aromatic Compounds Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 18. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. When a

Chapter 19 Aromatic Substitution Reactions Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 19. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. In the

Chapter 2 Molecular Representations Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 2. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. In bond-line

Chapter 20 Ketones and Aldehydes Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 20. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. The

Chapter 21 Carboxylic Acids and Their Derivatives Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 21. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary.

Chapter 22 Alpha Carbon Chemistry: Enols and Enolates Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 22. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary.

Chapter 23 Amines Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 23. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. Amines are ___________,

Chapter 24 Carbohydrates Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 24. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. Carbohydrates are polyhydroxy ___________

Chapter 25 Amino Acids, Peptides, and Proteins Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 25. Each of the sentences below appears verbatim in the section entitled Review of Concepts and

Chapter 26 Lipids Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 26. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. Lipids are naturally occurring

Chapter 27 Synthetic Polymers Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 27. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. Polymers are

Chapter 3 Acids and Bases Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 3. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. A

Chapter 4 Alkanes and Cycloalkanes Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 4. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary.

Chapter 5 Stereoisomerism Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 5. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. ______isomers have the same

Chapter 6 Chemical Reactivity and Mechanisms Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 6. Each of the sentences below appears verbatim in the section entitled Review of Concepts and

Chapter 7 Substitution Reactions Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 7. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. Substitution

Chapter 8 Alkenes: Structure and Preparation via Elimination Reactions Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 8. Each of the sentences below appears in the section entitled Review of Concepts and

Chapter 9 Addition Reactions of Alkenes Review of Concepts Fill in the blanks below. To verify that your answers are correct, look in your textbook at the end of Chapter 9. Each of the sentences below appears verbatim in the section entitled Review of Concepts and Vocabulary. Addition

Chapter 1 Multiple Choice Questions: Topic: General Section: Intro Difficulty Level: Easy 1. Chemical reactions occur as a result of: A) Attraction between opposite charges B) NucleusNucleus interactions C) Motion of electrons D) Like atoms interacting E) Combining two chemicals Ans: C Topic: General Section: 1.1 Difficulty Level:

Topic: Atomic orbital hybridization, bonding type Section: 1.9 Difficulty Level: Easy Topic: Atomic orbital hybridization, bonding type Section: 1.9 Difficulty Level: Easy Topic: Atomic orbital hybridization, bonding type Section: 1.9 Difficulty Level: Easy 93. The hybridization of nitrogen in trimethylamine, (CH3)3N:, is best described as: A) sp

Chapter 10 Multiple Choice Questions: Topic: Introduction to Alkynes Section: 10.1 Difficulty Level: Easy 1. For the molecule below, known as 2-pentyne, which of the following describes the orbital overlap of the C2C3 sigma bond? C CCH3CH2CH3 A) spsp B) sp2sp2 C) sp3sp3 D) pp E) sp3sp Ans:

Topic: Reduction of Alkynes Section: 10.5 Difficulty Level: Easy Topic: Reduction of Alkynes Section: 10.5 Difficulty Level: Easy Topic: Reduction of Alkynes Section: 10.5 Difficulty Level: Easy 61. Select the best reagent to convert 3-heptyne to trans-3-heptene? A) Na/NH3 B) 1 eq. NaNH2, NH3 C) xs NaNH2, NH3 D)

Topic: Halogenation of Alkynes Section: 10.8 Difficulty Level: Easy Topic: Halogenation of Alkynes Section: 10.8 Difficulty Level: Easy Topic: Halogenation of Alkynes Section: 10.8 Difficulty Level: Easy 114. Which of the compounds shown below would be the most likely product expected from the reaction scheme shown? ? (CH3)2CHCH(CH3)C Br Br Br Br I

Chapter 11 Testbank (Klein)- Draft 2 Chapter 11 Topic: Radicals Section: 11.1 Difficulty Level: Easy Chapter 11 Topic: Radicals Section: 11.1 Difficulty Level: Easy Chapter 11 Topic: Radicals Section: 11.1 Difficulty Level: Easy 1. Which of the following are the products of a homolytic cleavage of

Topic: Stereochemistry of Halogenation Section: 11.6 Difficulty Level: Difficult Topic: Stereochemistry of Halogenation Section: 11.6 Difficulty Level: Difficult Topic: Stereochemistry of Halogenation Section: 11.6 Difficulty Level: Difficult 41. Predict the major product(s) of the following reaction. h Br2 Br Br III III IV V Br Br Br Br BrBr Br Br Br A) I B) I and

HBr ROOR Br Br Br Br III III IV A) I B) II C) III D) IV E) I, II F) I, II, III, IV Ans: E Chapter 11 Topic: Radical Addition of HBr Section: 11.10 Difficulty Level: Difficult Ans: E Chapter 11 Topic: Radical Addition of HBr Section: 11.10 Difficulty Level: Difficult Ans:

Chapter 12 Testbank (Klein)- Draft 3 Chapter 12 Topic: One-Step Syntheses Section: 12.1 Difficulty Level: Easy 1. Predict the major product(s) for the following reaction: HBr Br Br I II Br III Br IV A) I B) II C) III D) IV E) I and III Ans: E Chapter 12 Topic: One-Step

Ans: Br2, hBrKOtBu 1) ozone2) DMSO Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Easy Ans: Br2, hBrKOtBu 1) ozone2) DMSO Chapter 12 Topic: How to Approach a Synthesis Problem Section: 12.4 Difficulty Level: Easy Ans: Br2, h Br KOtBu 1) ozone 2) DMS O

BA I II III IV VVI VII VIII Cl Br Br OH OH + En OH A) B = I and A = VI B) B = VI and A = I C) B = V and A = II D) B = IV and A = VII E) B = I and A = III F) B

Chapter Thirteen Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy Topic: Nomenclature of alcohols Section: 13.1 Difficulty Level: Easy 1. What is the IUPAC name for the following compound? CH3CHCHCHCHCH3 OH CH3 CH3 CH3 A) 4-isopropyl-3,4-dimethyl-2-butanol B) 2,3,4-trimethyl-4-pentanol C) 1,1,2,3-tetramethyl-4-pentanol D) 3,4,5-trimethyl-2-hexanol

55. Predict the product for the following reaction. O Ans: CH2OHHHO Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard O Ans: CH2OHHHO Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard O Ans: CH2OH H HO Topic: Preparation of Alcohols Section: 13.4 Difficulty Level: Hard COCH3 O 1. LiAlH4 2. H2O excess 56. Predict

86. Predict the product when cis-3-methylcyclopentanol is treated with TsCl/pyridine, followed by sodium bromide. A) trans-1-bromo-3-methylcyclopentane B) cis-1-bromo-3-methylcyclopentane C) 1-methylcyclopentene D) 2-Methylcyclopentene E) 3-Methylcyclopentene Ans: A Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium Ans: A Topic: Reactions of Alcohols Section: 13.9 Difficulty Level: Medium Ans: A Topic:

Chapter Fourteen Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy Topic: Nomenclature of Ethers Section: 14.2 Difficulty Level: Easy 1. What is the common name for CH3CH2CH2OCH2CH2CH3? A) dibutylether B) 1-propoxypropane C) 1-propoxyhexane D) dipropyl ether E)

55. Provide the structure for oxetane. Ans: O Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium Ans: O Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium Ans: O Topic: Nomenclature of epoxides Section: 14.7 Difficulty Level: Medium 56. Provide the IUPAC name for the following

83. Predict the product(s) for the following reaction. O 1. NaCN 2. H2O OH OH OH CN OH CN CN CN III III IV + enantiomer + enantiomer + enantiomer A) I B) II C) III D) IV E) none of these Ans: C Topic: Reactions of epoxides Section: 14.10 Difficulty Level: Easy Ans: C Topic: Reactions of

Chapter Fifteen Topic: Spectroscopy Section: 15.1 Difficulty Level: Easy Topic: Spectroscopy Section: 15.1 Difficulty Level: Easy Topic: Spectroscopy Section: 15.1 Difficulty Level: Easy 1. Which of the following is not true about electromagnetic radiation? A) frequency is directly proportional to wavelength B) frequency is directly proportional to energy

49. Which one of the following compounds is consistent with the following IR spectrum? SDBS: National Institute of Advanced Industrial Science and Technology OH O OH O OH III III IV OH V OH A) I B) II C) III D) IV E) V Ans: E Topic: Analyzing an IR spectrum Section: 15.6

Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium Topic: Analyzing the fragments Section: 15.12 Difficulty Level: Medium 80. Which of the following compounds will produce a prominent (M-18) peak in the mass spectrum? A) 2-methylheptane B) 1-heptanol

Chapter Sixteen Topic: Introduction to NMR Section: 16.1 Difficulty Level: Easy Topic: Introduction to NMR Section: 16.1 Difficulty Level: Easy Topic: Introduction to NMR Section: 16.1 Difficulty Level: Easy 1. Which of the following can not be probed by an NMR spectrometer? A) nucleus with odd number

51. Determine the multiplicity of each signal in the expected 1H NMR spectrum of the following compound. O Ans: Odoublet septettripletquartet Topic: Multiplicity Section: 16.7 Difficulty Level: Easy Ans: Odoublet septettripletquartet Topic: Multiplicity Section: 16.7 Difficulty Level: Easy Ans: O doublet septet triplet quartet Topic: Multiplicity Section: 16.7 Difficulty Level: Easy

83. Which of the following compounds will display five signals in the 13C NMR spectrum? Br Br Br Br Br Br Br Br III III IV A) I B) II C) III D) IV E) none of these Ans: A Topic: 13C NMR spectroscopy Section: 16.11 & 16.12 Difficulty Level: Medium Ans: A Topic: 13C NMR spectroscopy

Chapter Seventeen Topic: Classification of Dienes Section: 17.1 Difficulty Level: Easy Topic: Classification of Dienes Section: 17.1 Difficulty Level: Easy Topic: Classification of Dienes Section: 17.1 Difficulty Level: Easy 1. Which of the following compounds are isolated dienes? III III IV V A) I B) II C) III

Topic: Pericyclic Reaction Section: 17.6 Difficulty Level: Easy Topic: Pericyclic Reaction Section: 17.6 Difficulty Level: Easy Topic: Pericyclic Reaction Section: 17.6 Difficulty Level: Easy 55. What is the correct classification of the following pericyclic reaction? + A) electrophilic addition B) sigmatropic rearrangement C) cycloaddition D) electrocyclic reaction E) C

Topic: Diels-Alder Reaction Section: 17.7 Difficulty Level: Medium Topic: Diels-Alder Reaction Section: 17.7 Difficulty Level: Medium Topic: Diels-Alder Reaction Section: 17.7 Difficulty Level: Medium 80. What diene and dienophile would react to give the following Diels-Alder product? O O Ans: OO+ Topic: Diels-Alder Reaction Section: 17.7 Difficulty Level: Medium

Chapter Eighteen Topic: Nomenclature Section: 18.2 Difficulty Level: Easy Topic: Nomenclature Section: 18.2 Difficulty Level: Easy Topic: Nomenclature Section: 18.2 Difficulty Level: Easy 1. Toluene is the common name for: A) hydroxybenzene B) aminobenzene C) methylbenzene D) ethylbenzene E) methoxybenzene Ans: C Topic: Nomenclature Section: 18.2 Difficulty Level:

48. Which one of the following compounds is most acidic? IIII II IV A) I B) II C) III D) IV E) none of these Ans: A Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level: Easy Ans: A Topic: Aromatic, antiaromatic & nonaromatic Section: 18.5 Difficulty Level:

Chapter Nineteen Topic: Electrophilic Aromatic Substitution Section: 19.1 Difficulty Level: Medium 1. Cyclohexene undergoes addition reaction with bromine, but benzene does not. Instead benzene undergoes a substitution reaction with bromine. Explain. Ans: Cyclohexene has localized electrons, where as benzene has delocalized electrons. Addition of bromine results in

Topic: Electrophilic Aromatic Substitution Section: 19.11 Difficulty Level: Medium Topic: Electrophilic Aromatic Substitution Section: 19.11 Difficulty Level: Medium Topic: Electrophilic Aromatic Substitution Section: 19.11 Difficulty Level: Medium 43. Predict the major product for the following reaction. CH3 OCH3 Fuming H2SO4 Ans: OCH3SO3H Topic: Electrophilic Aromatic Substitution Section: 19.11 Difficulty

Topic: Synthesis Section: 19.12 Difficulty Level: Medium Topic: Synthesis Section: 19.12 Difficulty Level: Medium Topic: Synthesis Section: 19.12 Difficulty Level: Medium 63. Provide the reagents necessary to carry out the following conversion. CCl3 Cl Ans: 1. Cl2/FeCl3 2. CH3Cl /AlCl3 3. excess Cl2, heat Ans: 1. Cl2/FeCl3 2. CH3Cl /AlCl3

Chapter 2 Topic: Molecular Representations Section: 2.1 Difficulty Level: Easy Topic: Molecular Representations Section: 2.1 Difficulty Level: Easy Topic: Molecular Representations Section: 2.1 Difficulty Level: Easy 1. What is the molecular formula for the following structure? O A. C2H6O B. C4H6O C. C4H10O D. C2H4O Ans: C Topic:

Difficulty Level: Easy 61. Determine the number of lone pairs of electrons on the indicated atom. N A. 1 B. 2 C. 3 D. 4 Ans: B Topic: Lone Pairs Section: 2.5 Difficulty Level: Medium Ans: B Topic: Lone Pairs Section: 2.5 Difficulty Level: Medium Ans: B Topic:

Chapter Twenty Topic: Nomenclature Section: 20.2 Difficulty Level: Easy Topic: Nomenclature Section: 20.2 Difficulty Level: Easy Topic: Nomenclature Section: 20.2 Difficulty Level: Easy 1. What is the IUPAC name for the following compound? O A) 2-methyl-5-heptanone B) 7-methyl-4-octanone C) 6-isopropyl-4-octanone D) isobutyl propyl ketone E) 1,1-dimethyl-4-heptanone Ans: B

43. Predict the product for the following conversion. O O O H3O+ 1 mol Ans: OOOHOH Topic: Reactions of Aldehydes/Ketones Section: 20.5 Difficulty Level: Hard Ans: OOOHOH Topic: Reactions of Aldehydes/Ketones Section: 20.5 Difficulty Level: Hard Ans: O O OH OH Topic: Reactions of Aldehydes/Ketones Section: 20.5 Difficulty Level: Hard 44. Predict the product for the

75. Provide the product of the following reaction. NaBH4/CH3OH O OCH3 O OH OCH3 OO OH OH OH OH OCH3 OH I II III IV A) I B) II C) III D) IV Ans: A Topic: Reactions of Aldehydes/Ketones Section: 20.5 & 20.9 Difficulty Level: Hard Ans: A Topic: Reactions of Aldehydes/Ketones Section: 20.5 & 20.9 Difficulty Level: Hard Ans: A Topic: Reactions of

Chapter Twenty one Topic: Nomenclature Section: 21.2 Difficulty Level: Easy Topic: Nomenclature Section: 21.2 Difficulty Level: Easy Topic: Nomenclature Section: 21.2 Difficulty Level: Easy 1. What is the IUPAC name for the following compound? OH O A) methylpentanoic acid B) 3-methylpentanoic acid C) 2-methylhexanoic acid D) 3-methylhexanoic acid E)

Topic: Preparation & Reactions of acid chlorides Section: 21.8 Difficulty Level: Easy Topic: Preparation & Reactions of acid chlorides Section: 21.8 Difficulty Level: Easy Topic: Preparation & Reactions of acid chlorides Section: 21.8 Difficulty Level: Easy 49. Predict the product for the following reaction. OH O SOCl2 pyridine Cl O SO2Cl O OCl O OH O Cl III III IV A)

78. Predict the product for the following reaction. O O 1. DIBAH 2. H2O OH OH H O OH O OH OH III III IV A) I B) II C) III D) IV E) none of these Ans: B Topic: Preparation & Reactions of esters Section: 21.10 & 20.11 Difficulty Level: Medium Ans: B Topic: Preparation & Reactions of esters Section:

Chapter Twenty Two Topic: Enols & Enolates Section: 22.1 Difficulty Level: Easy Topic: Enols & Enolates Section: 22.1 Difficulty Level: Easy Topic: Enols & Enolates Section: 22.1 Difficulty Level: Easy 1. Which one of the following compounds is most acidic? A) ethyl acetoacetate B) 2-butanone C) ethyl pentanoate

39. Which one of the following is not a possible product when a crossed aldol addition reaction is carried out with ethanal and butanal as reactants? OH H OOH H O OH H OOH H O OH H O III III IV V A) I B) II C) III D) IV E) V Ans: B Topic: ldol reactions Section: 22.3 Difficulty Level: Medium Ans:

Topic: Alkylation of the -position Section: 22.5 Difficulty Level: Medium Topic: Alkylation of the -position Section: 22.5 Difficulty Level: Medium Topic: Alkylation of the -position Section: 22.5 Difficulty Level: Medium 70. Predict the product(s) for the following reaction. O 1. LDA 2. CH3CH2Br OOO O III III IV A) B)

92. Predict the product for the following reaction. 1. NaOCH3 3. H3O+ O O O 2. Br O O O O HO OH O O III III O IV O O V A) I B) II C) III D) IV E) V Ans: C Topic: Conjugate Addition Section: 22.6 Difficulty Level: Medium Ans: C Topic: Conjugate Addition Section: 22.6 Difficulty Level: Medium Ans: C

Chapter Twenty Three Topic: Nomenclature of amines Section: 23.2 Difficulty Level: Easy Topic: Nomenclature of amines Section: 23.2 Difficulty Level: Easy Topic: Nomenclature of amines Section: 23.2 Difficulty Level: Easy 1. What is the structure for 1-butanamine? A) CH3CH2CH2CH2NH2 B) CH3CH2NHCH2CH(CH3)2 C) (CH3CH2)2NCH2CH(CH3)2 D) (CH3CH2)4N+ OH- E) (CH3CH2)3CNH2

50. Provide the structures of the products in the following reaction sequence. APCC B(CH3)2NH C 1. BH3 2. H2O2, NaOH/H2OH2SO4, NaBH3CN Ans: OH O N(CH3)2ABC+ enantiomer + enantiomerN(CH3)2N(CH3)2N(CH3)2++ Topic: Preparation of amines Section: 23.6 Difficulty Level: Hard Ans: OH O N(CH3)2ABC+ enantiomer + enantiomerN(CH3)2N(CH3)2N(CH3)2++ Topic: Preparation of amines Section: 23.6 Difficulty

71. Provide the reagents necessary to carry out the following conversion. COH CN O Ans: COHCuCNCOHCNNNClCOHNO2OFe/HCl NaNO2/HCl< 50CNa2Cr2O7/H2SO4/H2OCH2CH3CH2CH3NO2CH3CH2Cl/AlCl3HNO3/H2SO4COHNH2OO O Topic: Reactions of amines Section: 23.10 & 23.11 Difficulty Level: Medium Ans: COHCuCNCOHCNNNClCOHNO2OFe/HCl NaNO2/HCl< 50CNa2Cr2O7/H2SO4/H2OCH2CH3CH2CH3NO2CH3CH2Cl/AlCl3HNO3/H2SO4COHNH2OO O Topic: Reactions of amines Section: 23.10 & 23.11 Difficulty Level: Medium Ans: COH CuCN COH CN NNCl COH NO2 O Fe/HCl NaNO2/HCl < 50C Na2Cr2O7/H2SO4/H2O CH2CH3CH2CH3 NO2 CH3CH2Cl/AlCl3HNO3/H2SO4 COH NH2 OO O

Chapter Twenty Four Topic: Classification of Carbohydrates Section: 24.2 Difficulty Level: Easy Topic: Classification of Carbohydrates Section: 24.2 Difficulty Level: Easy Topic: Classification of Carbohydrates Section: 24.2 Difficulty Level: Easy 1. Which of the following is a ketohexose? CH2OH O HHO OHH OHH CH2OH C OHH OHH OHH CH2OH O H C OHH HHO OHH OHH CH2OH O H D-lyxose D-fructose D-ribose D-glucose CH2OH O HHO OHH CH2OH D-xylulose C HHO HHO OHH CH2OH O H A) D-lyxose B)

47. Predict the product(s) for the following reaction. CH3OH HCl -D-galactopyranose Ans: OOHHOOHOCH3OOHHOOHOCH3+OH OH Topic: Reactions of Monosaccharides Section: 24.6 Difficulty Level: Medium Ans: OOHHOOHOCH3OOHHOOHOCH3+OH OH Topic: Reactions of Monosaccharides Section: 24.6 Difficulty Level: Medium Ans: O OH HO OH OCH3 O OH HO OH OCH3 + OH OH Topic: Reactions of Monosaccharides Section: 24.6 Difficulty Level: Medium 48. Predict

75. Which of the following pairs of D-aldohexoses would produce the same product when subjected to Wohl degradation? A) D-glucose & D-galactose B) D-mannose & D-galactose C) D-glucose & D-gulose D) D-allose & D-altrose E) D-glucose & D-allose Ans: D Topic: Wohl degradation Section: 24.6 Difficulty Level: Hard Ans:

Chapter Twenty Five Topic: Introduction to amino acids Section: 25.1 Difficulty Level: Easy Topic: Introduction to amino acids Section: 25.1 Difficulty Level: Easy Topic: Introduction to amino acids Section: 25.1 Difficulty Level: Easy 1. In -amino acids the amino and carboxylic acid groups are separated by ____,

54. Which of the following is a correct bond-line structure for a tripeptide Ser-Lys-Cys? H2N H N N H OH O O OS HO SH H2N H N N H OH O O OS HO SH H2N H N N H OH (CH2)4NH2 O O O HO SH H2N H N N H OH (CH2)4NH2 O O O HS OH III III IV A) I B) II C) III D) IV E) none of these Ans: A Topic: Structure of Peptides Section: 25.4 Difficulty Level: Medium Ans: A Topic: Structure of Peptides

Chapter Twenty Six Topic: Classification of Lipids Section: 26.1 Difficulty Level: Easy Topic: Classification of Lipids Section: 26.1 Difficulty Level: Easy Topic: Classification of Lipids Section: 26.1 Difficulty Level: Easy 1. Which one of the following is a complex lipid? A) steroids B) terpenes C) waxes D)

Topic: Phospholipids Section: 26.5 Difficulty Level: Medium Topic: Phospholipids Section: 26.5 Difficulty Level: Medium Topic: Phospholipids Section: 26.5 Difficulty Level: Medium 48. A lipid bilayer is formed by self assembly of _________. A) triglycerides B) saturated fatty acids C) phospholipids D) unsaturated fatty acids E) B & C Ans:

Chapter Twenty Seven Topic: Polymers Section: 27.1 Difficulty Level: Easy Topic: Polymers Section: 27.1 Difficulty Level: Easy Topic: Polymers Section: 27.1 Difficulty Level: Easy 1. Which one of the following is not a biopolymer? A) amylopectin B) DNA C) glycogen D) chitin E) none of these Ans: E

Topic: Polymer classification by reaction type Section: 27.4 Difficulty Level: Medium Topic: Polymer classification by reaction type Section: 27.4 Difficulty Level: Medium Topic: Polymer classification by reaction type Section: 27.4 Difficulty Level: Medium 42. Provide the structure of the polymer that is produced when phosgene is treated with 3,3- dimethyl-1,5-pentanediol.

Chapter 3 Topic: Introduction to Bronsted-Lowry Acids and Bases Section 3.1 Difficulty Level: Easy Topic: Introduction to Bronsted-Lowry Acids and Bases Section 3.1 Difficulty Level: Easy Topic: Introduction to Bronsted-Lowry Acids and Bases Section 3.1 Difficulty Level: Easy 1. Is the indicated compound acting an acid or a

Section 4 Difficulty Level: Easy 44. Identify the most acidic proton on the following compound. Hd Hb Hc Ha A. Ha B. Hb C. Hc D. Hd Ans: B Topic: Qualitative Bronsted-Lowry Acidity Section 4 Difficulty Level: Easy Ans: B Topic: Qualitative Bronsted-Lowry Acidity Section 4 Difficulty Level: Easy Ans: B

Chapter 4 Topic: Nomenclature Section 2 Difficulty Level: easy Topic: Nomenclature Section 2 Difficulty Level: easy Topic: Nomenclature Section 2 Difficulty Level: easy 1. What is the parent chain for the following compound? A. octane B. hexane C. heptane D. decane Ans: A Topic: Nomenclature Section 2 Difficulty Level:

Ans: Topic: Conformational Analysis of Butane Section 8 Difficulty Level: easy Ans: Topic: Conformational Analysis of Butane Section 8 Difficulty Level: easy Ans: Topic: Conformational Analysis of Butane Section 8 Difficulty Level: easy 57. Which of the following is the lowest energy conformer of the following compound? H H A.

Chapter 5 Topic: Isomerism Section 1 Difficulty: Easy Topic: Isomerism Section 1 Difficulty: Easy Topic: Isomerism Section 1 Difficulty: Easy 1. What is the relationship between the following two compounds? A. Constitutional isomers B. Stereoisomers C. Identical D. Not isomers, different compounds entirely. Ans: A Topic: Isomerism

Topic: Optical Activity Section 4 Difficulty: Hard Topic: Optical Activity Section 4 Difficulty: Hard Topic: Optical Activity Section 4 Difficulty: Hard 58. What is the % of the S enantiomer in a sample of carvone that has a specific rotation of -20, given that the specific rotation of R-carvone

Chapter 6 Topic: Enthalpy Section 6.1 Difficulty Level: Medium Topic: Enthalpy Section 6.1 Difficulty Level: Medium Topic: Enthalpy Section 6.1 Difficulty Level: Medium 1. Calculate the enthalpy of the following reaction. I+HBr Br +HI Ans: 8 kJ/mol Topic: Enthalpy Section 6.1 Difficulty Level: Medium Ans: 8 kJ/mol Topic:

O Ans: O Topic: Nucleophiles and Electrophiles Section 6.7 Difficulty Level: Easy Ans: O Topic: Nucleophiles and Electrophiles Section 6.7 Difficulty Level: Easy Ans: O Topic: Nucleophiles and Electrophiles Section 6.7 Difficulty Level: Easy 52. Identify the electrophilic atom in the following molecule. O A. C

Chapter 7 Topic: Introduction to Substitution Section 1 Difficulty Level: Easy Topic: Introduction to Substitution Section 1 Difficulty Level: Easy Topic: Introduction to Substitution Section 1 Difficulty Level: Easy 1. Which of the following is a substitution reaction? Br Br OOH Cl Br A. B. C. D. Ans: C Chapter 7 Topic: Introduction to Substitution

Br H2O Ans: OH Topic: SN1 Mechanism Section 5 Difficulty Level: Easy Ans: OH Topic: SN1 Mechanism Section 5 Difficulty Level: Easy Ans: OH Topic: SN1 Mechanism Section 5 Difficulty Level: Easy 75. What is the product of the following reaction. Include stereochemistry. Br H2O A. B. C.

Chapter 8 Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy 1. How substituted is the following alkene? Ans: Disubstituted Topic: Nomenclature of Alkenes Section 3 Difficulty: Easy Ans: Disubstituted Topic: Nomenclature of

60. Based upon the following energy diagram, is this reaction an E1 or an E2 elimination? Ans: E2 Topic: The E1 Mechanism Section 9 Difficulty: Medium Ans: E2 Topic: The E1 Mechanism Section 9 Difficulty: Medium Ans: E2 Topic: The E1 Mechanism Section 9 Difficulty: Medium 61. Based

Topic: Addition Reaction Mechanisms Section: 9.1 Difficulty Level: Easy Topic: Addition Reaction Mechanisms Section: 9.1 Difficulty Level: Easy Topic: Addition Reaction Mechanisms Section: 9.1 Difficulty Level: Easy Multiple Choice Questions: Multiple Choice Questions: Multiple Choice Questions: Ans: A Topic: Addition Reaction Mechanisms Section: 9.1 Difficulty Level: Moderate Ans: A Topic: