chemistry 233-001/002 exam 1 – version a

Chemistry233-001/002Exam1–VersionA

Fall2019 Dr.J.OsbournInstructions:Answerthefirst14questionsofthisexamusingthebubblesheetattachedtotheendofthisexambooklet.Youmaydetachthissheetifyouwish.Answertheremainingquestionsdirectlyonthisexam.Showallworkandprovidecompleteexplanations.

ThePeriodicTable

Multiple-ChoiceChoosethebestanswerforeachofthefollowingquestions.Recordeachanswerontheattachedbubblesheet.Ensureyoucompletelybubbleinyouranswers.(2pointseach)1. Inwhatorbitaldoesthenitrogenlonepairresideinthefollowingmolecule?

a. sp2b. spc. sp3d. pe. noneoftheabove

2. WhatistheenergycostassociatedwiththeH/Feclipseinthefollowingconformation?Therelative

energy(Erel)oftheconformationis3.3kcal/mol.

a. 0.3kcal/mol b. 1.0kcal/molc. 1.3kcal/mold. 1.5kcal/mol

3. Howmanyhydrogenarebondedtothecarbonbearingthenegativechargeinthefollowing

structure?

a. zerob. one c. twod. threee. four

4. Inthefollowinggroupofcompounds,_____isthestrongestbasewhile_____istheweakestbase.

a. I,IIIb. II,Ic. III,IId. III,Ie. II,III

5. WhatistheCH3/CH3dihedralangleinthefollowingNewmanprojection?

a. 90°b. 120°c. 60°d. 45°e. 180°

N

H

F

H

H

HH

N N N

I II III

H

H

CH3

CH3

HH

6. Whatistheformalchargeonsulfurinthefollowingmolecule?

a. zerob. +1c. +2d. -1e. -2

7. WhatisthehybridizationofatomsAandB?

a. A=sp2;B=sp3b. A=sp3;B=sp2 c. A=sp2;B=sp2d. A=sp3;B=sp3e. Noneoftheabove

8. Whichofthefollowingcontainsanamideandathiolfunctionalgroup?

9. Whicharrowbestdescribesthefollowingacid/basereaction?

10. Howwouldthefollowingcomplexsubstituentbenamedwhenattachedtoaparent(P)chain?

a. 5-methylhexylb. 1-ethyl-3-methylbutylc. 3-(5-methylethyl)d. 1-ethyl-2-isoproylethyl

NH2

S NH

O

SHN

SH N

H

O

SH

a b c d

NH + H

H? NH2 +

H

a.

b.

c.

H3CS O

O OH

ANH3B

P

11. Whatisthemostacidicprotoninthefollowingmolecule?

12. Howmanyioniccompoundsarepresentintheboxshownbelow?

a. zerob. onec. two d. threee. four

13. Inthefollowingmolecule,_____isthestrongestC-Csinglebondand_____istheweakestC-Csinglebond.

a. I,IIb. II,Ic. I,IIId. III,Ie. III,II

14. Whatistheorbitaloverlapinvolvedinthefollowingbond?

a. Cp-Opb. Csp2-Osp2c. Csp2-Osp2&Cp-Opd. Csp2-Osp&Cp-Ope. Noneoftheabove

SH

HN HO

SH

H

a

b

c

d

OLi Cl KBr

Na BH2 NH H

I IIIII

O

H

CompletionSectionAnswertheremainingquestionsdirectlyontheexamitself.Pleasewriteneatlyanddarklyasyouranswerswillbescanned.15. WritetheIUPACnameforeachmoleculeshownbelow.(3pointseach)

16. Circleandidentifythefunctionalgroupsinthefollowingmolecule.(4points)

17. Foreachofthefollowing,usetheprovidetemplatetocompletetheNewmanprojectionor3Dstructure.(2pointseach)

NewmanProjection 3DStructure NewmanProjection 3DStructurea.template

b.template

a.

b.

c.

F

Cl Cl

O

O

O

OH

NH2

H BrCH3

HCl

HOH3C

18. Drawthehighestenergyandlowestenergyconformationsof2-methylbutaneviewingalongtheC2-C3bond.(3pointseach) HighestEnergyConformation LowestEnergyConformation

19. Usethemoleculeshownbelowtoanswerthefollowingquestions.Note:Allappropriatehydrogen

aredrawninonnon-carbonatoms!(2pointseach)

a.Drawinalllonepairs.

b.Writeintheformalchargeonanychargedatoms.

c.Whatisthehybridizationofthefollowingatoms?

X_______________Y_______________

d.ThegeometryatcarbonZis________________________________.

e.Howwouldyouclassifythealcohol(i.e.1°)?

20. DrawavalidLewisorskeletalstructureforC4H8O.(4points)

21. Completetheacid/basereactionshownbelowbydrawingtheconjugateacidandconjugatebaseintheappropriatespaces.Thencircletheequilibriumarrowthatbestrepresentsthedirectionofthereaction.(4points)

O

O

OH

NH

HHY

X

Z

+ HS +

Conjugate Acid Conjugate Base

22. Drawtheproductsofthefollowingacid/basereactionandincludecurvedarrowstoshowelectronflow.(4points)

23. Foreachofthefollowing:I.Drawtheadditionalresonancestructures;II.Addcurvedarrowsonthe

firststructuretoshowelectronflow;III.Circlethemajorresonancecontributor.(5pointseach)

24. Circlethestrongeracidineachpairandprovideaverybriefexplanation.(3ptseach)

25. Convertthefollowingskeletalstructuretoacondensedstructure.(3points)

26. Thefollowingcompoundcontains_______sigmabondsand_______pibonds.(3points)

27. Drawthreevalidisomersofheptane.(3points)

+H N H

H

H

O

OH

a.

b.

N

O

F OH vs Br OH SH vs SH

Br

H

O