chemistry 233-001/002 exam 1 – version a
TRANSCRIPT
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