ORGANICCHEMISTRY FALL2017 LANEYCOLLEGECHEM12A(L1/L1L) INSTRUCTOR:S.CORLETTEXAM1Practice Page1of7 1. Carvoneisanaturalproductfoundinspearmintandcarawayseed. (10points) a. Whatisthemolecularformulaforcarvone? b. Namethefunctionalgroupsfoundincarvone?2. DrawamoleculethathasthemolecularformulaC4H5NO2.Thestructuremustcontainonlythe“common”

functionalgroupsdiscussedinChapter2(itcouldhavemorethanone!)andshouldbeshownusingbond-linestructureswithlonepairsofelectronsclearlyshown.

Also,namethefunctionalgroupsshowninyourstructure. (20points)

ORGANICCHEMISTRY FALL2017 LANEYCOLLEGECHEM12A(L1/L1L) INSTRUCTOR:S.CORLETTEXAM1Practice Page2of7 3. Forthefollowingmolecules,

a. Drawbond-linedrawingsthatshowtheexpectedgeometry(usedashesandwedgeswherenecessary).b. Showallofthelonepairsofelectrons.c. Indicatewhetherthemoleculehasapermanentdipolemoment(µ≠0D),ifitdoes,thenindicatethe

directionoftheoveralldipole,orifitdoesn’thaveapermanentdipolemoment(µ=0D) (15points)

CCl4 CH3OH C2H2Br2(thereismorethanoneanswerforthisone)4. Assignformalcharges(ifnon-zero)totheappropriateatomsinthefollowingmolecules(orions). (Notethatalllonepairsofelectronsareshownineachstructure) (10points)

ORGANICCHEMISTRY FALL2017 LANEYCOLLEGECHEM12A(L1/L1L) INSTRUCTOR:S.CORLETTEXAM1Practice Page3of7 5. Considerthestructureshownbelow. (25points) a. Labelthehybridizationforeachoftheatoms(excepthydrogen). b. Whattypeofatomicorbitaldoesthelonepaironthenitrogenoccupy? c. WhatistheapproximatebondanglefortheC-N-Cbond? d. Whichbondislonger,N=CorC=S?Explain.6. Foreverybondinthemolecule,indicatewhichtypeofbonditis(πorσ)andwhatatomicorbitalsareusedto

formthem(hybridizedorbitalsareconsideredatomicorbitals).Also,whattypeoforbitalisthelonepairofelectronsin.(note:therearesevenbondsthatneedidentifying). (20points) (15points)

ORGANICCHEMISTRY FALL2017 LANEYCOLLEGECHEM12A(L1/L1L) INSTRUCTOR:S.CORLETTEXAM1Practice Page4of7 7. Imidazoleisshownbelow.Indicatethehybridizationforeachofthenitrogenatomsandwhattypeoforbital

eachthelonepairofelectronresidesin. (10points)8. By“pushing”electrons,showtheotherresonanceformfortheionsshownbelow.Circlethemajorresonance

formandprovidethereasonforyourchoice. (20points)9. Ammonia(NH3)hasadipolemoment(µ)of1.42D,whereasnitrogentrifluoride(NF3)hasavalueof0.234D.

Suggestareasonforthedramaticdifferencebetweenthesetwootherwisesimilarmolecules.(Hint:carefullyconsiderthestructureandgeometry) (10points)

ORGANICCHEMISTRY FALL2017 LANEYCOLLEGECHEM12A(L1/L1L) INSTRUCTOR:S.CORLETTEXAM1Practice Page5of7 10. ThepKavaluesforthefollowingcompoundsare10.5,14.4,and16.0,irrespectively. a. Assignthesevaluestothecorrespondingcompounds. b. Whichcompoundisthemostacidic?Whichistheleastacidic c. UseARIOtojustifyyouranswers(don’tforgetabouttheconj.bases) (20points) 11. GiventhepKadatabelow,indicatewhichsideoftheequilibriumisfavored(i.e.,rightorleft).Also,explainwhy

thedataindicatethis–beclearaboutthis.Calculatetheequilibriumconstant(Keq)–showyourcalculation. (15points)

12. TaxolisanaturalproductthatwasfirstisolatedfromthebarkofthePacificyewtree(Taxusbrevifolia)in1967.

Inthelate1970sitwasfoundtobeapowerfulanticanceragent.Indeed,themoleculeisverydensewithfunctionalgroups!Circleandidentifyasmanyofthecommonfunctionalgroupsasyoucan(thereareatleast12). (26points)

ORGANICCHEMISTRY FALL2017 LANEYCOLLEGECHEM12A(L1/L1L) INSTRUCTOR:S.CORLETTEXAM1Practice Page6of7 13. NameeachofthefollowingcompoundsusingIUPAC(systematic)names. (20points)14. Drawstructuresforthefollowingcompounds. (20points) a.3-methyl-5-(2-methylpropyl)decane b.cis-1,3-diisopropylcycloheptane

15. Considerthemoleculebelow.UsingNewmanprojections,drawthelowestenergyandthehighestenergy

conformationsaroundtheC3-C4bond.Ineachconformation,labelitasstaggeredoreclipsed,andindicatewhattypeofstrainispresent–torsional,steric,angle,orsomecombinationofthem–bespecificaboutthis.

(50points)

ORGANICCHEMISTRY FALL2017 LANEYCOLLEGECHEM12A(L1/L1L) INSTRUCTOR:S.CORLETTEXAM1Practice Page7of7 16. Drawbothchairformsofthecompoundcis-1-ethyl-1-methylcyclohexane.Calculatetheequilibriumconstant

(Keq)betweenthetwochairsat25°Cfromtheleasttothemoststablechair(leaststablechaironleftofequilibrium–moststableontheright).Giventhefollowingformulasanddata

Keq=e-ΔG/RT R=8.314J/mol·K K=°C+273.15

1,3-DiaxialInteractions−CH3 7.6kJ/mol−CH2CH3 8.0kJ/mol