Organic Chemistry Reactions and Mechanisms, Exams of Nursing

Download Organic Chemistry Reactions and Mechanisms and more Exams Nursing in PDF only on Docsity! 1 1. The following molecule contains primary, secondary, tertiary, and quaternary carbon atoms. Select the answer that best describes the type of carbon atoms in the molecule below. The molecule has: a) 5 primary carbon atoms and 3 secondary carbon atoms b) 1 quaternary carbon atom and 7 secondary carbon atoms c) 2 tertiary carbon atoms and 5 primary carbon atoms d) 3 secondary carbon atoms and 2 tertiary carbon atoms e) 1 tertiary carbon atom and 7 secondary carbon atoms 2. How many lone pairs of electrons does this molecule have? Note: all formal charges are shown. A lone pair of electrons are two unbonded electrons paired together on an atom. a) 2 b) 3 c) 4 d) 5 e) 6 f) 7 g) 8 h) 9 i) 10 j) 11 2 2 5 5. Consider the most basic atom on the following molecule: Which hybridization diagram below matches the most basic atom? 6. Consider the following 4 organic solvents: 2-butanone, 2-propanol, 1-butanol, and 1-butylamine. Which of the following statements is true about these 4 organic solvents? a) All 4 solvents can form hydrogen bonds with diethyl ether b) There are 2 polar protic solvents c) There is 1 polar aprotic solvent d) 1-butylamine forms the strongest hydrogen bonds with itself e) 2-propanol has the weakest intermolecular forces because it is branched 6 4 7 b) 1 7. Which of the following solvents can hydrogen bond with themselves? 1) 2-fluoro-3-pentanone 2) diethyl ether 3) iso-propanol 4) dimethylamine a) 1 and 2 b) 1 and 3 c) 1 and 4 d) 2 and 3 e) 2 and 4 f) 3 and 4 g) 1, 3 and 4 h) 1, 2 and 3 i) 1, 2 and 4 j) 2, 3 and 4 8. Consider all valid resonance structures of the molecule shown below. The number of different resonance structures that bear a negative charge on an oxygen atom are: a) 0 c) 2 d) 3 e) 4 f) 5 10 6 11 11. Which hydrogen atom is the most acidic? 12. Which structure represents the Newman projection shown? 12 7 15 15. Which of the following molecules would be optically active? a) Only 1 b) Only 2 c) Only 3 d) 1 and 2 e) 1 and 3 f) 2 and 3 g) 1, 2 and 3 16. Which of the following molecules is a meso compound? 16 9 17 17. Which two compounds represent a pair of enantiomers? a) 1 and 2 b) 1 and 3 c) 1 and 4 d) 2 and 3 e) 2 and 4 f) 3 and 4 18. Which of the following statements is false regarding the reaction scheme shown below: 20 11 CHEM 266 Term Test #1 7:00 pm Fall 2020 Confidentiality and Statement of Honesty The midterm exam is open book and you may use any resource, including the internet during the exam. This examination is protected by copyright. Reproduction or dissemination of this document or the contents or format of this document in any manner whatsoever (e.g., sharing the content with other students), without the express permission of the instructor, is strictly prohibited and will be subject to disciplinary action as outlined in Policy 71. By starting and submitting this exam to be graded you have agreed to:  Keeping the content of this examination confidential until test answers have been posted.  Completing the examination by yourself and not receiving help from anyone during the examination period. Students who engage in academic dishonesty will be subject to disciplinary action under Policy 71 1) Consider the molecule shown below. Which of the following functional groups is not shown in this molecule? Alcohol b) Alkene c) Ether d) Amine e) Ketone Carboxylic acid Amide 2) Which of the following molecules does not contain a bond angle of 120⁰? a) (CH3CH2)2N − (nitrogen has a negative charge) b) cyclohexanone c) (CH3)2CO d) ethanal e) CH3COOCH3 f) pentanamide f) g) a) CHEM 266 Term Test #1 7:00 pm Fall 2020 3) Which of the following molecules contains a secondary alcohol? 4) How many atoms in the following molecule have the hybridization shown in the atomic potential energy diagram? Lone pairs of electrons are not shown, but formal charges are. CHEM 266 Term Test #1 7:00 pm Fall 2020 7) Which of the following compounds would have a higher boiling point than N-methylpentamine? 1) 4-hexanone 2) 1,4-dihydroxybutane 3) cyclohexanol 4) triethylamine a) Only 1 b) Only 2 c) Only 3 d) Only 4 e) 1 and 4 f) 2 and 3 g) 2 and 4 1, 2 and 3 i) 2, 3 and 4 j) 1, 3 and 4 8) Consider all valid resonance structures of the following molecule. How many different oxygen atoms will gain a negative charge through the delocalization of the negative charge (i.e. resonance)? a) 0 b) 1 c) 2 d) 3 h) CHEM 266 Term Test #1 7:00 pm Fall 2020 e) 4 f) 5 CHEM 266 Term Test #1 7:00 pm Fall 2020 9) Which of the following molecules cannot form hydrogen bonds with itself? a) H2O b) iso-propylamine c) tert-butanol d) hydrofluoric acid e) triethylamine f) Hexanoic acid 10) Consider all valid resonance structures of the following molecule. Including the given structure, how many atoms will gain a positive charge from the delocalization of electrons (i.e. resonance)? a) 0 b) 1 c) 2 d) 3 4 f) 5 g) 6 h) 7 i) 8 e) CHEM 266 Term Test #1 7:00 pm Fall 2020 13) Rank the following acids in order of acidity (most acidic to least acidic). a) 1 > 2 > 3 b) 1 > 3 > 2 c) 2 > 1 > 3 d) 2 > 3 > 1 e) 3 > 1 > 2 f) 3 > 2 > 1 14) Rank the following acids in order of acidity (most acidic to least acidic). a) 1 > 2 > 3 b) 1 > 3 > 2 c) 2 > 1 > 3 d) 2 > 3 > 1 e) 3 > 1 > 2 f) 3 > 2 > 1 15) Rank the following acids in order of acidity (most acidic to least acidic). a) 1 > 2 > 3 b) 1 > 3 > 2 c) 2 > 1 > 3 d) 2 > 3 > 1 e) 3 > 1 > 2 f) 3 > 2 > 1 CHEM 266 Term Test #1 7:00 pm Fall 2020 16) Rank the following bases in order of basicity (most basic to least basic). a) 1 > 2 > 3 b) 1 > 3 > 2 c) 2 > 1 > 3 d) 2 > 3 > 1 e) 3 > 1 > 2 f) 3 > 2 > 1 17) Which of the following equilibrium equations has the smallest K value (K = equilibrium constant, smallest K favours reactants)? CHEM 266 Term Test #1 7:00 pm Fall 2020 CHEM 266 Term Test #1 7:00 pm Fall 2020 20) Which of the following molecules is polar aprotic? a) Cyclohexanol b) Diethylamine c) Water d) Diethyl ether e) 2-butyne END OF QUESTIONS Ofloxacin is an antibacterial compound with the following structure: 1) What is the stereochemistry of the indicated double bond and stereocenter in Ofloxacin (stereocenter is indicated with an asterisk *)? a) Z, R b) Z, S c) E, R d) E, S 2) Which of the following functional groups is not present in Ofloxacin? a) Ketone b) Ether c) Amine d) Alkene e) Alcohol 3) Determine the most basic atom in Oxfloxacin. Which hybridization diagram below matches the most basic atom? 4) Which of the following molecules has the most non-bonding electrons (lone pairs of electrons)? ) C) and D 5) Which of the following compounds has a higher boiling point than diethylamine? A) trimethylamine B) butylamine C) 1-butanol D) sec-butanol a ) b) A) and B) c) Only C) d) B), C) and D) e) A), B), C) and D) 6) Which of the following molecules is polar aprotic? a) Ethanol b) Diisopropylamine c) Diethylether d) Sulfuric acid e) Hexane 7) Consider the major resonance contributor for the following molecule: Which of the following statements is true about the major resonance contributor? a) All resonance structures have one negative charge on a carbon atom, making them all equal b) The most stable resonance structure has the negative charge on the alcohol oxygen atom c) The most stable resonance structure has the negative charge on the ketone oxygen atom 13) Consider the structure of (R)-3-methylhexane. Which of the following statements is true about the most stable Newman conformation when looking down the C3-C4 bond? a) In the most stable Newman conformation two hydrogen atoms are eclipsed. b) In the most stable Newman conformation two ethyl groups are gauche. c) In the most stable Newman conformation two ethyl groups are anti. d) In the most stable Newman conformation, an ethyl group and a methyl group are anti. e) In the most stable Newman conformation, an ethyl group and a hydrogen atom are anti. 14) Which of the following chair structures represents the most stable conformation of cis-1,2- dichloro-4-ethylcyclohexane? 15) Which of the following molecules are not optically active? a) 1, 2 and 3 b) 1 and 5 c) 4 and 5 d) 1 and 4 e) All of the above 16) The following compounds are described as: a) Meso compound b) Enantiomers c) Diastereomers d) Constitutional isomers e) Different drawings of the same compound 17) Which pair of molecules represents a pair of diastereomers? 4 6 8 5 2 7 3 1 9 Consider the following energy diagram shown below: 19) Which of the following is the best leaving group in an SN2 reaction? m m m 55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn 132.9 137.3 138.9 178.5 180.9 183.9 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 (210) (210) (222) Cesium Barium Lanthanu Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon m 87 88 89 104 105 106 107 108 109 Fr Ra Ac Unq Unp Unh Uns Uno Une (223) 226.0 (227) (261) (262) (263) (264) (265) (266) Francium Radium Actinium 1) Structures 1 and 2 each have two basic atoms. Classify the more basic atom in each compound as a Strong Base (SB) or Weak Base (WB) and a Good Nucleophile (GN) or a Poor Nucleophile (PN). Note: many molecules have more than one basic atom and remember that basicity is relative; an atom that is a weak base is still stronger than a very weak base. a) 1) SB, PN 2) SB, GN b) 1) SB, PN 2) WB, GN c) 1) SB, PN 2) WB, PN d) 1) SB, GN 2) SB, PN e) 1) SB, GN 2) WB, GN f) 1) SB, GN 2) WB, PN g) 1) WB, GN 2) SB, PN h) 1) WB, GN 2) WB, PN i) 1) WB, PN 2) WB, GN j) 1) WB, PN 2) WB, PN 2) Which of the following molecules is the most basic? 3) Which of the following molecules is the most nucleophilic in a polar protic solvent? The following electrophiles are reacted with NaCN in acetone. Rank the electrophiles from fastest to slowest with respect to a substitution reaction with NaCN. a) 1 > 2 > 3 b) 1 > 3 > 2 c) 2 > 1 > 3 d) 2 > 3 > 1 e) 3 > 1 > 2 f) 3 > 2 > 1 4) Which of the following starting materials would react the fastest when treated with concentrated H2SO4? Consider the following reaction. What is the configuration of the carbons labeled i) and ii) in the product(s) of this reaction? Is the product(s) optically active or not optically active? Configuration of product Optical activity of the resulting product(s) a) i) R ii) R optically active b) i) R ii) S optically active c) i) S ii) S optically active d) i) S ii) R optically active e) i) R ii) R not optically active f) i) R ii) S not optically active g) i) S ii) S not optically active h) i) S ii) R not optically active i) i) mix of R,S ii) R Optically active 9) 10) j) i) mix of R,S ii) S Optically inactive 11) Which of the following compounds will most readily undergo rearrangement in an SN1 reaction when treated with H2O? a) 3-bromo-7-methyldecane b) 3-bromo-3-methyldecane c) 2-bromo-3,3-dimethyldecane d) (E)-3-bromohept-3-ene e) (Z)-4-bromohept-3-ene What statement(s) is/are correct about the following reaction? 1) The major product is a tetrasubstituted alkene 2) The major product has an E configuration 3) The major product has a Z configuration 4) The major product is a monosubstituted alkene 5) The major product is an amine with an S configuration 6) The major product is an amine with an R configuration a) 1 and 2 are correct b) 1 and 3 are correct c) 4 and 2 are correct d) 4 and 3 are correct e) Only 1 is correct 12) What statement(s) is/are correct about the following reaction. 1) Two major products are produced, which are diastereomers 2) One major product is produced, which is meso 3) Two major products are produced, which are enantiomers 4) A solution of the major products is optically inactive 5) A solution of the major products is optically active a) 1 and 4 are correct b) 1 and 5 are correct c) 2 and 4 are correct d) 2 and 5 are correct e) 3 and 4 are correct f) 3 and 5 are correct 16) What is the major product formed in the following reaction sequence? Note: (+) means racemic mixture (the structure shown plus its enantiomer). NaH is a non- nucleophilic base. 15) 17) What is the major product(s) for the following reaction? a) 3 and 4 are the major products b) 2 and 4 are the major products c) 2 and 3 are the major products d) 1 and 2 are the major products e) 1 and 3 are the major product f) 1 and 4 are the major products 18) The major product(s) for the following reaction is/are best described as: a) A single chiral product b) A single achiral molecule c) A 1:1 mixture of diastereomers d) A single meso compound e) A racemic mixture CHEM 266 Term Test #2 7:00 pm Fall 2020 CHEM 266 Term Test #2 7:00 pm Fall 2020 3) Which of the following statements is true about the most stable Newman conformation of the given molecule when looking down the C3-C4 bond? a) In the most stable Newman conformation two ethyl groups are gauche. b) In the most stable Newman conformation two methyl groups are anti. c) In the most stable Newman conformation two hydrogen atoms are eclipsed. d) In the most stable Newman conformation, an ethyl group and a methyl group are anti. e) In the most stable Newman conformation, an ethyl group and a methyl group are gauche. The most stable conformation of (1R, 2R, 3R)-1-bromo-2-chloro-3- fluorocyclohexane has: a) Bromine equatorial, chlorine equatorial, fluorine equatorial b) Bromine axial, chlorine equatorial, fluorine equatorial c) Bromine equatorial, chlorine equatorial, fluorine axial d) Bromine axial, chlorine equatorial, fluorine axial e) Bromine equatorial, chlorine axial, fluorine equatorial 4) CHEM 266 Term Test #2 7:00 pm Fall 2020 5) Which of the following molecules has an enantiomer? a) 1 and 3 b) 1 and 4 c) 2 and 5 d) 3 and 5 e) 2, 3 and 5 f) 2, 3 and 4 g) 3, 4 and 5 h) 1, 2, 3 and 4 i) 2, 3, 4 and 5 j) All of the above The following compounds may be described as: a) Enantiomers b) Diastereomers c) Constitutional isomers d) Meso compound e) Different drawings of the same compound 6) CHEM 266 Term Test #2 7:00 pm Fall 2020 10) Which of the following electrophiles would react the fastest in an SN2 reaction? 11) Rank the following molecules from most reactive to least reactive when treated with NaCN in acetone: a) 1 > 2 > 3 b) 1 > 3 > 2 c) 2 > 1 > 3 d) 2 > 3 > 1 CHEM 266 Term Test #2 7:00 pm Fall 2020 e) 3 > 1 > 2 f) 3 > 2 > 1 CHEM 266 Term Test #2 7:00 pm Fall 2020 12) From the following pairs molecules, select the most basic: a) 1, 3, 5 b) 1, 3, 6 c) 1, 4, 5 d) 1, 4, 6 e) 2, 3, 5 f) 2, 3, 6 g) 2, 4, 5 h) 2, 4, 6 13) From the following pairs of molecules, select the most nucleophilic in a polar protic solvent: a) 1, 3, 5 b) 1, 3, 6 c) 1, 4, 5 d) 1, 4, 6 e) 2, 3, 5 f) 2, 3, 6 g) 2, 4, 5 h) 2, 4, 6 CHEM 266 Term Test #2 7:00 pm Fall 2020 ¢) yw a YN NS SCH>CH3 CHEM 266 Term Test #2 7:00 pm Fall 2020 18) Which of the following statements is true regarding the major product(s) formed in the following reaction: a) A meso compound is produced b) A racemic mixture is produced c) An equal mixture of diastereomers is produced d) An achiral product is produced e) The substituents in the product are “trans” to each other 19) The major product(s) of the reaction shown below can be described as: a) A single meso compound b) A racemic mixture c) An equal mixture of diastereomers d) A single chiral product e) A mixture of constitutional isomers CHEM 266 Term Test #2 7:00 pm Fall 2020 20) What is the major product formed in the following reaction? END OF QUESTIONS 4) Determine which reaction would occur faster in diethyl ether from the pairs of substitution reactions shown below: a) 1, 4 b) 1, 3 c) 2, 4 d) 2, 3 5) What is the stereochemistry of the major product of this reaction? a) 3S, 5R b) 3R, 5S c) 3R, 5R d) 3Z, 5S e) Racemic Mixture 6) Which of the following reactions matches the reaction coordinate diagram shown? The potential energy scale refers to the potential energy of the organic molecule during a reaction or series of reactions and not the free energy of the system. \P NaOMe reaction coordinate MeOH 7) What is the major product of the following reaction? 8) How is the major product(s) of the following reaction best described? a) A trisubstituted alkene b) One chiral molecule c) A meso compound d) A pair of diastereomers e) A pair of enantiomers 9) What is the major product(s) of the following reaction? 10) What is the major product(s) of the following reaction? 11) What is the major product formed in the following reaction? 15) What is the major product formed in the following reaction? Periodic Table: (1) IA (18) Noble Gases 1 2 H He 1.008 (2) KEY (13) (14) (15) (16) (17) 4.003 Hydrogen IIA IIIA IVA VA VIA VIIA Helium 3 4 47 Atomic Number 5 6 7 8 9 10 Li Be Ag SYMBOL B C N O F Ne 6.941 9.012 107.9 Atomic Weight 10.81 12.01 14.01 16.00 19.00 20.18 Lithium Beryllium Silver Name Boron Carbon Nitrogen Oxygen Fluorine Neon 11 12 13 14 15 16 17 Na Mg Al Si P S Cl Ar 22.99 24.31 (3) (4) (5) (6) (7) (8) (9) (10) (11) (12) 26.98 28.09 30.97 32.06 35.45 39.95 Sodium Magnesi um IIIB IVB VB VIB VIIB VIIIB VIIIB VIIIB IB IIB Aluminum Silicon Phosphor us Sulfur Chlorine Argon 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 K Ca Sc Ti V Cr Mn Fe Co Ni Cu Zn Ga Ge As Se Br Kr 39.10 40.08 44.96 47.90 50.94 52.00 54.94 55.85 58.93 58.71 63.55 65.37 69.72 72.59 74.92 78.96 79.90 83.80 Potassium Calcium Scandium Titanium Vanadium Chromium Manganese Iron Cobalt Nickel Copper Zinc Gallium Germanium Arsenic Selenium Bromine Krypton 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 Rb Sr Y Zr Nb Mo Tc Ru Rh Pd Ag Cd In Sn Sb Te I Xe 85.47 87.62 88.91 91.22 92.91 95.94 98.91 101.1 102.9 106.4 107.9 112.4 114.8 118.7 121.8 127.6 126.9 131.3 Rubidium Strontiu Yttrium Zirconium Niobium Molybdenu Technetium Rutheniu Rhodium Palladium Silver Cadmium Indium Tin Antimony Tellurium Iodine Xenon m m m 55 56 57 72 73 74 75 76 77 78 79 80 81 82 83 84 85 86 Cs Ba La Hf Ta W Re Os Ir Pt Au Hg Tl Pb Bi Po At Rn 15) What is the major product formed in the following reaction? 132.9 137.3 138.9 178.5 180.9 183.9 186.2 190.2 192.2 195.1 197.0 200.6 204.4 207.2 209.0 (210) (210) (222) Cesium Barium Lanthanu Hafnium Tantalum Tungsten Rhenium Osmium Iridium Platinum Gold Mercury Thallium Lead Bismuth Polonium Astatine Radon m 87 88 89 104 105 106 107 108 109 Fr Ra Ac Unq Unp Unh Uns Uno Une (223) 226.0 (227) (261) (262) (263) (264) (265) (266) Francium Radium Actinium 3) Which of the following statements best describes the relative acidity of the molecules shown below: a) The least acidic compound is acid 1 because it does not have inductive stabilization b) The most acidic compound is acid 1 because it has resonance stabilization over two oxygen atoms c) The least acidic compound is acid 3 because it does not have resonance or inductive stabilization d) The most acidic compound is acid 2 because it has resonance over one oxygen and one chlorine atom e) The most acidic compound is acid 3 because the charge is on a chloride ion which is larger than oxygen f) The least acidic compound is acid 2 because oxygen is larger than chlorine 4) Which of the following molecules contains an atom that has one electron in the 2p orbital? a) Sodium methoxide b) iso-Butanol c) Diethylamine d) 2-Pentanone e) 1-Methoxypropane + 1) EtOH2 2) EtOH 3) C6H5OH 4) AcOH 5) Me2NH 6) HC≡CH 5) Consider relevant resonance structures for the following molecule. How many different carbon atoms will the positive charge delocalize onto? a) 2 b) 3 c) 4 d) 5 e) 6 f) 7 g) 8 h) 9 6) For the following pairs of acids (1 and 2, 3 and 4, 5 and 6), select the strongest acid: a) 1, 3, 5 b) 1, 3, 6 c) 1, 4, 5 d) 1, 4, 6 e) 2, 3, 5 f) 2, 3, 6 g) 2, 4, 5 h) 2, 4, 6 11) Consider the most stable chair conformation of the molecule shown below. What is the dihedral angle between the two chloro groups when looking down the C1-C2 bond? a) 45° b) 60° c) 109.5° d) 120° e) 180° 12) The structure of codeine is shown below. How many sp2 hybridized carbon atoms are present in this molecule? a) 5 b) 6 c) 7 d) 8 e) 9 f) 10 13) What is the stereochemistry of the major products 1 and 2 in the following reactions? a) Product 1: R, Product 2: R b) Product 1: S, Product 2: S c) Product 1: R, Product 2: S d) Product 1: S, Product 2: R e) Product 1: S, Product 2: achiral f) Product 1: achiral, Product 2: R g) Product 1: R, Product 2: achiral h) Product 1: achiral, Product 2: S 14) Which of the following compounds can hydrogen bond with themselves? a) Diethyl ether (CH3CH2)2O b) Triethylamine (CH3CH2)3N c) Acetic acid CH3COOH d) Ammonium chloride NH4Cl e) 3-fluoropropanal CH2FCH2CHO 1) The leaving group is a hydroxide anion 17) Which of the following statements are true concerning the mechanism of the following reaction? The leaving group is water 3) The first step in the mechanism is a proton transfer 4) The first step in the mechanism is a nucleophilic attack by the iodide ion 5) The reaction follows an SN2 mechanisms 6) The reaction follows an SN1 mechanisms a) 1, 4, and 5 are correct b) 1, 4, and 6 are correct c) 1, 3, and 5 are correct d) 1, 3, and 6 are correct e) 2, 3, and 5 are correct f) 2, 3, and 6 are correct g) 2, 4, and 5 are correct h) 2, 4, and 6 are correct 18) Which of the following reactions would produce a racemic mixture as the major products? 2) 19) What statement(s) are true about the major products in the following reactions: i) Product 1 is a trisubstituted alkene ii) Product 2 is a trisubstituted alkene iii) Product 1 is a disubstituted alkene iv) Product 2 is a disubstituted alkene v) Product 1 produces the less stable alkene as the major product a) i and ii are true b) i, ii, and v are true c) i and iv are true d) i, iv, and v are true e) ii and iii are true f) ii, iii, and v are true g) iii and iv are true h) iii, iv and v are true 20) Which electrophile has the best leaving group for an SN2 reaction?