Practice Tests, Organic Chemistry I Table Of Contents

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1Practice Tests, Organic Chemistry I Table of ContentsOnline Organic Chemistry I, Chem 350, Dr. Craig P. Jasperse, Minnesota State University MoorheadFor full class website, anic-chemistry-i-350-fall-spring/TestTest 1 Version 1Test 1 Version 2Test 1 Version 3Test 1 Version 4Page391521Test 2 Version 1Test 2 Version 2Test 2 Version 3Test 2 Version 427333943Test 3 Version 1Test 3 Version 2Test 3 Version 3Test 3 Version 449556167Test 4 Version 1Test 4 Version 2Test 4 Version 3737985Final Exam Version 1Final Exam Version 293101

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31JASPERSECHEM 350 TEST 1VERSION 1 Organic Chemistry I - JasperseIntro and ReviewStructure and Properties of Organic MoleculesStructure, Nomenclature, and Conformation/Stereochemistry of Alkanes1. Draw the correct Lewis structure of CH3CN. (Needn’t show 3-D geometry) (3pt)2. Draw the correct Lewis structure for HOCH2CHO. (Needn’t show 3-D geometry). (3pt)3. Draw a 3-dimensional picture for the atoms in CH3CO2CH2NHCH3, using the hash-wedgeconvention. (You needn’t specify lone pairs, and orbitals need not be shown). (5pt)4. For the structure shown, what is the hybridization, electron-pair geometry, and approximatebond angle (90, 109, 120, or 180) relative to: (6pt)13 4HO 2O75 6 N 8H9electron-pair bondhybridization geometryangleelectron-pair bondhybridization geometryangleO-1C-5C-2N-7C-3O-95. Assign any formal charges to any apropriate atoms for proline, given the structure shown (oneof the body’s 20 monomers from which protein and enzyme biopolymers are constructred). (3pt)OONH 21

426. Rank the acidity of the following, from 1 (most) to 4 (least). (4pt)OHOHNHO7. Which of the following represent pairs of resonance structures? (4pt)a.b.c.OCH 3OCH 3BrBrd. Both a and ce. a, b, and c are all resonance structures.8. Draw arrows to show electron-movement in the following two steps (draw arrows for eachstep). Draw a circle around the atom that functions as nucleophile in step 1, and a square aroundthe atom that functions as nucleophile in step 2. (5pt)OBrStep 1 OHOBrStep 2OH(anion)O BrOH9. Rank the series on the basis of boiling point, 1 having highest boiling point, 3 having lowest.(3pt)OOH10. Rank the series on the basis of water solubility, 1 having highest solubility, 3 having lowest.(3pt)OHOH2

5311. For each of the following pairs of resonance structures, circle the one that would make agreater contribution to the actual resonance hybrid. (4pt)OOOCH3OCH3(anions)12. Cyclopropane is much more “strained” than cyclopentane. Why? (Short!) (3pt)13. For the following acid-base reaction,a. put a box around the weakest base in the reactionb. put a circle around the weakest acidc. draw an arrow to show whether the equilbrium goes to the right or left. (4pt)OONa H 2OO NaOHOH14. Classify the relationship between the pairs of molecules as either: (8pt)same compoundstructural isomersresonance structuresgeometric isomersnot isomers (different molecular formulas)OHOHHCH3CH3H HHHCH3HBrBrH CH3HH3OHHHHOH

6415. Give the name for the following. (7pt)HHCH316. Identify all the funtional groups in the following molecules. (Do not include “alkane”, sincethat isn’t “functional”.) (6pt)ONOOOOH17. Which of the following pair will have the larger rotation barrier, relative to the bondsindicated? (3pt)18. For the following Newman projections, rank them in stability from 1 to 4, 1 being moststable. Identify the “anti” conformation, the “gauche” conformation, and the “totally eclipsed”conformation. (6pt)HCH3CH3 HH HHHCH3HH3CCHHHCH3H3HHH3CHH3CHHH19. Draw the Newman projection for the most stable conformation of 1,2-dichloroethane. (3pt)4

7520. Draw the two chair conformations of cis-1-ethyl-4-methylcyclohexane. (You don’t have todraw all the hydrogens). (5pt)21. Which is more stable, cis- or trans-1-t-butyl-2-methylcyclohexane?conformation of the more stable isomer. (4pt)Draw the best22. Draw as many structural isomers as you can for C6H14. Be careful not to draw the sameisomer twice! I will take off points for duplicating! (6pt)5

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91JASPERSECHEM 350 TEST 1VERSION 2 Organic Chemistry I - JasperseIntro and ReviewStructure and Properties of Organic MoleculesStructure, Nomenclature, and Conformation/Stereochemistry of Alkanes1. Draw the correct Lewis structure of CH3CO2CH2COCH3. (Needn’t show 3-D geometry) (3pt)2. Draw a 3-dimensional picture for the atoms in CH3CH2CHCHCH2NHCH2CHO, using the hashwedge convention. (You needn’t specify lone pairs, and orbitals need not be shown). (5pt)3. For the structure shown, what is the hybridization, electron-pair geometry, and approximate bondangle (90, 109, 120, or 180) relative to: (7pt, 2 points off for each error)O13O245NHelectron-pair bondhybridization geometryangle6electron-pair bondhybridization geometryangleC-1C-4O-2N-5C-3C-64. Assign any formal charges to any appropriate atoms for the structure shown below. (4pt)OHOON CH 3CH 3

1025. Rank the acidity of the following, from 1 (most) to 4 (least). (4pt)HOOHNH 2O6. For the following pairs, identify as “isomers” (“I”) or “resonance structures” (“R”). (6pt)OOOHOH7. Draw arrows to show electron-movement in the following reactions. (These are reactions, notresonance.) (5pt)OO Bra.HH BrOHOO HOb.8. Rank the series on the basis of boiling point, 1 having highest boiling point, 3 having lowest. (3pt)NH 2NH 29. Rank the series on the basis of water solubility, 1 having highest solubility, 3 having lowest. (3pt)OHOH

11310. Circle whichever of the following could fit the formula C5H10? (3pt)11. For the following acid-base reaction,a. put a box around the weakest base in the reactionb. put a circle around the weakest acidc. draw an arrow to show whether the equilibrium goes to the right or left. (4pt)OH NHNaONa ONH 2O12. Classify the relationship between each pair of molecules as either: (10 pt)same compoundstructural isomersresonance structuresstereoisomersH 3COiPrHHH 3COHBriPrHCH 3CH 3HHHHCH2CH 3H BrBrHHNBrHHN

4 1214. Give the name for the following. (7pt)HH15.16. Identify and write down the names for each of the functional groups in each of the followingmolecules. (Do not include “alkane”, since that isn’t “functional”.) For each molecule, try to writethe names in order, as they appear from left-to-right in the molecules. (8pt)OOHOOHONH 2ONH17. Circle which of the following pair will have the larger rotation barrier, relative to the bondsindicated? (2pt) Identify which reason explains why: steric strain, torsional strain, or angle strain?18. For the following Newman projections: (6pt total)a. rank them in stability from 1 to 4, 1 being most stableb. identify the “anti”, “gauche”, and the “totally eclipsed” conformations.HHCH 3HHHHHHCH2CH 3H 3CH2CCH 3HHH 3CHHCH2CH 3HHHH 3CH 3CH2CHc. Is the energy difference between the gauche and the anti conformation based on steric strain,torsional strain, or angle strain?d. In the case of ethane (not shown), staggered conformations are better than eclipsedconformations. Is the difference based on steric strain, torsional strain, or angle strain?19. Draw both the most stable and the least stable Newman projections for 1-bromopropane,BrCH2CH2CH3, relative to C1-C2 bond. - (3pt)

13520. Which of the following are correct Lewis structures, including formal charges, for nitric acid,HNO3. (3 pts)OH N OOa.b.c.d.e.21.A onlyB onlyC onlyBoth A and CAll of the aboveAOH O NBOOH O N OC22. Draw the two chair conformations of cis-1-isopropyl-4-methylcyclohexane. (You don’t have todraw all the hydrogens). (5pt) (Use “iPr” as abbreviation).23. Draw the best chair conformation of the more stable isomer. Which is more stable, cis- or trans-1butyl-2-methylcyclohexane? (4pt)24. Draw any 6 of the 9 possible structural isomers for alkanes with formula C7H16. When decidingwhether to draw cyclic or acyclic alkanes, make sure that you fit the formula! Be careful not todraw the same isomer twice! I will take off points for duplicating! (You can try to show off bygetting more than 6, but if you do still be sure you don’t duplicate!) (6pt)

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1JASPERSECHEM 350 TEST 1VERSION 3 Organic Chemistry I - JasperseIntro and ReviewStructure and Properties of Organic MoleculesStructure, Nomenclature, and Conformation/Stereochemistry of Alkanes1. (12 points) Give the relationship between the following pairs of structures. The possiblerelationships are the following:same compoundstructural isomersresonance structuresstereo isomersnot isomers (different molecular formula)a.HBrBrHH Brb. H C C HBr Hc.BrHBrBr HH HH C C HBr BrBrd.e.f.2.(8 points) Draw line-angle structures and names for 4 of the 5 structural isomers of C6H14.115

2OH 2N23456OH783. (10 Points)a. For the above structure, what is the hybridization and approximate bond angles (109, 120, or180) about:1C-2C-4C-6O-8b. In the above structure, N-1 is actually found to have 120º bond angles. (This may seemunexpected to you at this point, but we’ll learn why later in the course.) What must be thehybridization of the nitrogen?4.(2 Points) Bond rotation around C6-C7 in the above structure has a 7 kcal/mol barrier, whilerotation around the C4-C5 bond has a 70 kcal/mol barrier. Explain very briefly why it is somuch harder to rotate the latter bond?5. (4 points) For each of the pairs listed, circle the one with the higher boiling point.a.CH3Nb.HNOHOH6. (6 points) Write a Lewis structure and assign any non-zero formal charges.a. [CH3NH3] b. CH3CO2Nac. CH3CHO216

37.(5 points) a) Draw the best resonance structure for anion A, and circle the resonancestructure that would make the greater contribution to the resonance hybrid.ONAb. For the two resonance structures shown below, circle the resonance structure that would makethe greater contribution to the resonance hybrid. NHNH22 8.(6 points) Rank the acidity of the following molecules, 1 being most acidic, 4 being leastacidic. Hint: draw the anions!NH3CH3CH2OHCH3CO2HHCl9. (6 points)Draw a line-angle picture for all of the atoms in the moleculeCH3CH2COCHClCH3, including the hydrogens. Use the hash-wedge convention to indicateatoms that are not in the plane of the paper.10. (5 points) Rank the ring strain in the following, from 1(most) to 3 (least). Explain verybriefly the differences in strain.ABC317

411. (6 points) Which of the following are capable of cis-trans stereoisomerism? (Yes/No).a. 3-ethyl-1,1-dimethylcyclopentaneb. 3-pentene (name means a double bond is between carbons 3 and 4)c. 1,3-dimethylcyclohexane12. (9 points) Identify the functional groups in the following molecules. (Do not include"alkane", since that is not "functional". And do not specify "cyclic".)a. H 2NCO 2H("GABA: brain neurotransmitter")OHCH 3HCH 3 Hb.HOHTestosteroneCH 3 OONCH 3Hc.OHCocaineO418

513. (5 points) Give the IUPAC name for the following compounds.Ha.b.HCH 3CH 2CH 2CH 314. (8 points) a. Draw Newman projections for the totally eclipsed, the gauch, and the anticonformations of 2,5-dimethylhexane, relative to the C3-C4 bond. You may abbreviate theisopropyl groups attached to C3 and C4 as "i-Pr" for convenience.b. Explain very briefly why the rotation barrier around the C3-C4 bond of 2,5-dimethylhexane isgreater than the rotation barrier in butane.43 i-Pr43i-Pr15. (8 points) a.) Draw the two chair conformations of cis-3-methyl-1-isopropylcyclohexane.(You don't need to show the H's on carbons other than 1 and 3). For convenience, you mayabbreviate methyl as "Me" and isopropyl as "iPr"b.) Circle the more stable conformation.c) Would trans-3-methyl-1-isopropylcyclohexane be more stable or less stable than the cisisomer?519

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1JASPERSECHEM 350 TEST 1VERSION 4 Organic Chemistry I - JasperseIntro and ReviewStructure and Properties of Organic MoleculesStructure, Nomenclature, and Conformation/Stereochemistry of Alkanes1. Order the following according to increasing electronegativity, 1 being highest, 4 lowest. (2pts)NFOC2. Write Lewis structures and assign any non-zero formal charges. (3pts each)a. [CH3OH2] b. CH3CO2CH2ONac. CH3CHCHCONH23. For each of the following, a) draw its resonance structure, and for each pair b) circle thestructure that would make the greater contribution to the resonance hybrid. (2 pts each)Oa.Hb.O 4. Draw line-angle structures for 7 of the 9 structural isomers of C7H16. (5 pts)21

25. For the following pairs of structures, identify them as either: Resonance Structures, StructuralIsomers, Stereoisomers, or Same. (2 pts each)OHOa.b.HCH 3HH 3CCH 3HHH 3Cc.d.e.CH3CH2CH2CH2CH3(CH3)2CHCH2CH36. Rank the acidity of the following molecules, 1 being most acidic, 4 being least acidic. (3 pts)CH3NH2O7.CH3OH CH 3HCO2HOCH3CH3 CH4a) Put a box around the weakest base in the above reaction. (1pt)b) Put a circle around the weakest acid in the above reaction. (1pt)c) Draw an arrow to show whether at equilibrium the reaction will go left-to-right or right-toleft. (2pt)22

38. Draw the line-angle structure for the following condensed structural formula: (CH3CH2)2CO(3pt)9.H 2N123456789a. For the above structure, what is the hybridization, electron-pair geometry, and approximatebond angles (109, 120, or 180) about: (6pt)N-1C-3C-5C-8b. Rank the length of the following bonds, 1 being shortest, 3 being longest. (2pt)C2-C3C4-C5C8-C910. For each of the pairs listed, circle the one with the higher boiling point. (4pt)a.OOHb.c.O11. Draw a 3-dimensional picture for all of the atoms (hydrogens included) in the moleculeCH3CHCHCOCH2CH2NHCH3. Your picture should use the hash-wedge convention toillustrate atoms that are not in the plane of the paper, and should reflect approximate bondangles. (5pt)23

412. Draw a 3-D picture of CH2O showing the π bond as well as the four atoms. (3pt)13. For the following set, rank the solubility in water, from 1 (most soluble) to 4 (least soluble).(3pt)OHOHO14. Identify the functional groups in the following molecules. (8pt)a.b.OOOHONHOH15. Give the IUPAC name for the following compounds. (6pt)a.b.CH 3HHCH 324

516. Draw the Newman projections for the best and worst conformations of butane, and give thenames for these conformations. Briefly explain what “strain factors” make the worstconformation worse than the best conformation. (6pt)17. a.) Draw both chair conformations of cis-1-methyl-2-isopropylcyclohexane. Draw thesubstituents and H-atoms attached to carbons 1 and 2. (You don't need to show the H's on theother carbons). (4pt)b.) Circle the more stable conformation. (1pt)18. Draw the best chair conformation for 1,3-diethylcyclohexane, and identify whether it is “cis” or“trans”. (3pt)19. Use the arrow-pushing convention to show the electron-movement mechanisms for the followtwo reactions. (5pt)a.O OCH 3CH 3OH2b.NH 2 OH2NH 225

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27JASPERSE CHEM 350 TEST 2VERSION 1Ch. 4 The Study of Chemical Reactions; Ch. 5 StereochemistryCh. 6 Alkyl Halides: Nucleophilic Substitution and Elimination1. Predict the major organic product for each of the following. (3 points each)Br2, hvBrCH3SNaINaOCH2CH32. Show an alkyl bromide and some nucleophile that you could use to make the following bySN2. (3 points)OCH2CH 33. For the structure shown,a. Draw the major elimination productformed upon treatment with H2O/heat.DHBrHHCH3b. Draw the major elimination productformed upon treatment with CH3CH2ONa.c. Draw the major substitution productformed upon treatment with CH3CH2ONa.(3 points each)

28(3 points for each multiple choice question)4. Which of the following is true regarding an SN1 reaction?a. It would be faster at 25 than 50 b. It would be faster in ethanol than in pentanec. Keeping the moles of reactants constant but doubling the quantity of solvent woulddecrease the rate by a factor of 4.d. Stereochemical inversion occurs exclusively6. Which of the following statements is true?a. The rate determining step is always the last step in a reaction mechanism.b. The stability/reactivity principle says that the more stable of two chemicals will be morereactivec. The reactivity/selectivity principle says that the more reactive of two chemicals will be lessselective.d. The activation barrier for a reaction is the difference in energy between reactants and finalproducts.7. Which of the following statements is true about the chlorination of methane?a. In each propagation step a radical is producedb. 6.02 x 1023 initiation events are needed to make one mole of chloromethanec. Most chloromethane is made by combination of a methyl radical with a chlorine radicald. The overall chlorination of methane is strongly endothermic.8. Which of the following statements is FALSE?a. Optically active solutions solutions always contain chiral molecules.b. Two diastereomers always have identical melting pointsc. Optically inactive solutions are either racemic or else contain no chiral chemicals at alld. A solution with 60% optical purity would have an 80/20 mix of enantiomers9. When the reactants shown undergo substitution, which of the products A-D will form? (3points)DBrHa.b.c.d.e.HHCH3A onlyB onlyA and BA, B, and CA, B, C, and DH2OheatD?HOHHDHHDHOH DHCH3CH3 HCH3 HCH3 HOHH AOH BH CH D

2910. Rank the reactivity of the structures shown toward the reactant(s) indicated on the left (1being most, etc.) (3 points each)BrNaOCH2 CH3BrIBrBr2/hvOCH3BrNHLiOLiOHBrH2O, heat,BrBrBr11. Carbocations often rearrange, as shown below. Draw in the hydrogens on the two carbonsinvolved in the rearrangement, and show formal arrow-pushing to illustrate the transformation.(3 points) 12. Draw the mechanism for the following reaction, propagation steps only. (4 points)Br2, hvBr

3013. Draw (3R,6R)-6-bromo-3-chloro-2-methyloctane (3 points)14. Name the following: (3 points)HBr(opticallyactive)HCl15. Classify each of the chiral carbons in the following structures as R or S (there may be morethan one in a molecule). (10 points)HOHCH3HH CH3H ClBr H16. a. Classify each pair as diastereomers, enantiomers, or same. (12 points)b. For the first structure of each pair, circle it if it is not chiralc. For the first structure of each pair, write “meso” by it if it is mesoHOHOHHOHHOHHH BrBr H H BrH BrCl BrHFBr FClH17a. a) Draw all the unique stereoisomers of 2,3-dichlorobutane. Cross out any duplicates.b) Identify which is meso. c) Identify a pair that are related as diastereomers. (5 points)

3118. Draw the mechanisms for the following reactions, using formal arrow pushing. Note: insome case hydrogens that are not illustrated will be involved in bond changes. You would dowell to write them in at the beginning. (12 points total, 3/3/6 distribution)Br NaOHBrBrOHNaOHH2OheatOH(identify the slow step)

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33JASPERSE CHEM 350 TEST 2VERSION 2Ch. 4 The Study of Chemical ReactionsCh. 5 SterochemistryCh. 6 Alkyl Halides: Nucleophilic Substitution and Elimination1. Rank the reactivity of the following molecules toward Br2/hv. (1 most, 4 least) (3 points)CH3-CH32. Rank the reactivity of the following molecules toward ethanol and AgNO3. (1 most, 4 least)(3 points)BrClClBr3. Rank the reactivity of the following molecules toward NaOCH3. (1 most, 4 least) (3 points)BrBrI4. Rank the reactivity of the following toward 1-iodopropane. (1 most, 4 least) (3 points)CH3ONaCH3CO2HCH3CO2Na5. What is the hybridization of a carbocation? (2 points)CH3SNaBr

346. Predict the major organic product (1 major structure is all that is needed in each case) for eachof the following reactions. (Minor products or inorganic side products need not be drawn.)(3 points each)Br CH3CO2Na Br2Br HhvAcetone NaI Solvent7. Draw the structures for intermediate A and final product B. (4 points)Br2, hvANaOCH3B8. Draw the product when the following substance undergoes E2 elimination. ("D" is deuterium,basically just a labelled hydrogen). If the starting material is optically active, will the product byoptically active? (4 points)H 3C BrHCH3 NaOCH3HD

359. Show an alkyl bromide and some nucleophile that you could use to make the fol

18. For the following Newman projections: (6pt total) a. rank them in stability from 1 to 4, 1 being most stable b. identify the “anti”, “gauche”, and the “totally eclipsed” conformations. c. Is the energy difference between the gauche and the anti conformation based on steric strain, torsional strain, or angle strain? d.

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