ACS ORGANIC CHEMISTRY II FINAL
EXAMINATION QUESTIONS WITH
100% CORRECT ANSWERS
What gvis gvthe gvIUPAC gvpriority gvfor gvnaming? gv- gvANSWERS-Carboxylic gvacid gv>
gvKetone gv> gvAldehyde gv> gvAlcohol
In gvIUPAC gvnaming, gvwhat gvis gvthe gvsuffix gvused gvfor gvketone gvgroups? gv-
gvANSWERS--one
In gvIUPAC gvnaming, gvwhat gvis gvthe gvsuffix gvused gvfor gvalcohol gvgroups? gv-
gvANSWERS--nol
In gvIUPAC gvnaming, gvwhat gvis gvthe gvsuffix gvused gvfor gvesters? gv- gvANSWERS--noate
Benzyl gvgroup gv- gvANSWERS-
Phenyl gvgroup gv- gvANSWERS-
ethanoic gvacid gv- gvANSWERS-
(E) gvisomers gvvs. gv(Z) gvisomers. gvWhich gvone gvis gvobserved gvwhen gvthe gvhigher
gvranked gvmolecules gvare gvon gvthe gvsame gvside? gvopposite? gv- gvANSWERS-highest
gvon gvsame gvside: gvZ
highest gvon gvopposite gvsides: gvE
Electron-withdrawing gvgroups gvare gvwhat gvtype gvof gvdirectors? gvWhat gvis gvthe gvone
gvand gvonly gvexception? gv- gvANSWERS-Meta gv(deactivators) gv
Halogens
If gvthe gvatom gvdirectly gvattached gvto gvthe gvaromatic gvring gvhas gvlone gvpairs gvwhat gvtype
gvof gvdirector gvis gvit? gvwhat gvif gvit gvdoes gvnot gvhave gvlone gvpairs? gv- gvANSWERS-lone
gvpairs: gvactivating, gvortho, gvpara gvdirector
no gvlone gvpairs: gvdeactivating, gvmeta gvdirector
When gvare gvthe gvterms gvortho, gvmeta, gvpara gvused? gv- gvANSWERS-when gvthere gvare
gv2 gvsubstituents gvon gvthe gvaromatic gvring
In gvIUPAC gvnaming, gvwhat gvis gvNH2 gvon gva gvphenyl gvring gvreferred gvto gvas? gv-
gvANSWERS-aniline
Analine gv- gvANSWERS-
Amine gv- gvANSWERS-
, Amide gv- gvANSWERS-
If gvthere gvis gva gvNO2 gvgroup gvpresent, gvwhat gvIUPAC gvprefix gvwill gvalso gvbe gvevident?
gv- gvANSWERS-nitro
What gvis gvthe gvpredicted gvreaction? gv1º gvalkyl gvhalide gvwith gva gvstrong gvbase? gvweak
gvbase? gvpoor gvnucleophile? gv- gvANSWERS-strong gvbase: gvSn2 gvfavored gvbut gvE2
gvwith gvstrong gvnon-nucleophilic gvbases
weak gvbase: gvSn2
poor gvnucleophile: gvno gvreaction
What gvis gvthe gvpredicted gvreaction? gv2º gvalkyl gvhalide gvwith gva gvstrong gvbase? gvweak
gvbase? gvpoor gvnucleophile? gv- gvANSWERS-strong gvbase: gvmostly gvE2
strong gvnon-nucleophilic gvbases: gvmostly gvSn2
poor gvnucleophile: gvSn1/E2 gv(slow) gvin gvpolar, gvprotic gvsolvents
What gvis gvthe gvpredicted gvreaction? gv3º gvalkyl gvhalide gvwith gva gvstrong gvbase? gvweak
gvbase? gvpoor gvnucleophile? gv- gvANSWERS-strong gvbase: gvE2
strong gvnon-nucleophilic gvbases: gvSn1/E1 gvin gvpolar gvprotic gvsolvents
poor gvnucleophile: gvSn1/E1 gvin gvpolar, gvprotic gvsolvents
What gvis gvthe gvconfiguration gvof gvthe gvproduct gvin gvthe gvbase-catalyzed gvhydrolysis gvof
gv(R)-1-choloro-1-deuteriobutane? gv- gvANSWERS-(S)-1-deuterio-1-butanol gv(Sn2)
Where gvis gvthe gvlargest gvmolecule gvon gvthe gvperiodic gvtable? gv- gvANSWERS-Bottom
gvlefthand gvcorner
Nucleophilic gvstrength gvincrease gvwith gvincreasing gvwhat? gv- gvANSWERS-atomic gvsize
Which gvalkyl gvvalid gvwould gvyou gvexpect gvto gvundergo gvSn1 gvhydrolysis gvmost
gvrapidly?
I, gvBr,Cl, gvor gvF? gv- gvANSWERS-I
In gvwhich gvreaction gvis gva gvracemic gvmixture gvobtained?
In gvwhich gvreaction gvis gvan gvinversion gvof gvchirality gvobtained? gv- gvANSWERS-
inversion: gvSn2
racemic gvmix: gvSn1
Cleavage gvof gvan gvether gvusually gvrequires gva gvstrong gvacid gvthat gvhas gva gvconjugate
gvbase gvwhich gvis gva gvstrong gvnucleophile, gvsuch gvas...? gvDepending gvon gvthe gvtype gvof
gvalkyl gvgroup, gvthe gvacid gvreaction gvwith gvthe gvhalide gvion gvproduces gvwhat? gv-
gvANSWERS-HBr
HI
alkyl gvhalide gvand gvan gvalcohol
When gvchirality gvrotates gvclockwise gvthe gvchirality gvis... gv- gvANSWERS-R
When gvchirality gvrotates gvcounterclockwise gvthe gvchirality gvis... gv- gvANSWERS-S
EXAMINATION QUESTIONS WITH
100% CORRECT ANSWERS
What gvis gvthe gvIUPAC gvpriority gvfor gvnaming? gv- gvANSWERS-Carboxylic gvacid gv>
gvKetone gv> gvAldehyde gv> gvAlcohol
In gvIUPAC gvnaming, gvwhat gvis gvthe gvsuffix gvused gvfor gvketone gvgroups? gv-
gvANSWERS--one
In gvIUPAC gvnaming, gvwhat gvis gvthe gvsuffix gvused gvfor gvalcohol gvgroups? gv-
gvANSWERS--nol
In gvIUPAC gvnaming, gvwhat gvis gvthe gvsuffix gvused gvfor gvesters? gv- gvANSWERS--noate
Benzyl gvgroup gv- gvANSWERS-
Phenyl gvgroup gv- gvANSWERS-
ethanoic gvacid gv- gvANSWERS-
(E) gvisomers gvvs. gv(Z) gvisomers. gvWhich gvone gvis gvobserved gvwhen gvthe gvhigher
gvranked gvmolecules gvare gvon gvthe gvsame gvside? gvopposite? gv- gvANSWERS-highest
gvon gvsame gvside: gvZ
highest gvon gvopposite gvsides: gvE
Electron-withdrawing gvgroups gvare gvwhat gvtype gvof gvdirectors? gvWhat gvis gvthe gvone
gvand gvonly gvexception? gv- gvANSWERS-Meta gv(deactivators) gv
Halogens
If gvthe gvatom gvdirectly gvattached gvto gvthe gvaromatic gvring gvhas gvlone gvpairs gvwhat gvtype
gvof gvdirector gvis gvit? gvwhat gvif gvit gvdoes gvnot gvhave gvlone gvpairs? gv- gvANSWERS-lone
gvpairs: gvactivating, gvortho, gvpara gvdirector
no gvlone gvpairs: gvdeactivating, gvmeta gvdirector
When gvare gvthe gvterms gvortho, gvmeta, gvpara gvused? gv- gvANSWERS-when gvthere gvare
gv2 gvsubstituents gvon gvthe gvaromatic gvring
In gvIUPAC gvnaming, gvwhat gvis gvNH2 gvon gva gvphenyl gvring gvreferred gvto gvas? gv-
gvANSWERS-aniline
Analine gv- gvANSWERS-
Amine gv- gvANSWERS-
, Amide gv- gvANSWERS-
If gvthere gvis gva gvNO2 gvgroup gvpresent, gvwhat gvIUPAC gvprefix gvwill gvalso gvbe gvevident?
gv- gvANSWERS-nitro
What gvis gvthe gvpredicted gvreaction? gv1º gvalkyl gvhalide gvwith gva gvstrong gvbase? gvweak
gvbase? gvpoor gvnucleophile? gv- gvANSWERS-strong gvbase: gvSn2 gvfavored gvbut gvE2
gvwith gvstrong gvnon-nucleophilic gvbases
weak gvbase: gvSn2
poor gvnucleophile: gvno gvreaction
What gvis gvthe gvpredicted gvreaction? gv2º gvalkyl gvhalide gvwith gva gvstrong gvbase? gvweak
gvbase? gvpoor gvnucleophile? gv- gvANSWERS-strong gvbase: gvmostly gvE2
strong gvnon-nucleophilic gvbases: gvmostly gvSn2
poor gvnucleophile: gvSn1/E2 gv(slow) gvin gvpolar, gvprotic gvsolvents
What gvis gvthe gvpredicted gvreaction? gv3º gvalkyl gvhalide gvwith gva gvstrong gvbase? gvweak
gvbase? gvpoor gvnucleophile? gv- gvANSWERS-strong gvbase: gvE2
strong gvnon-nucleophilic gvbases: gvSn1/E1 gvin gvpolar gvprotic gvsolvents
poor gvnucleophile: gvSn1/E1 gvin gvpolar, gvprotic gvsolvents
What gvis gvthe gvconfiguration gvof gvthe gvproduct gvin gvthe gvbase-catalyzed gvhydrolysis gvof
gv(R)-1-choloro-1-deuteriobutane? gv- gvANSWERS-(S)-1-deuterio-1-butanol gv(Sn2)
Where gvis gvthe gvlargest gvmolecule gvon gvthe gvperiodic gvtable? gv- gvANSWERS-Bottom
gvlefthand gvcorner
Nucleophilic gvstrength gvincrease gvwith gvincreasing gvwhat? gv- gvANSWERS-atomic gvsize
Which gvalkyl gvvalid gvwould gvyou gvexpect gvto gvundergo gvSn1 gvhydrolysis gvmost
gvrapidly?
I, gvBr,Cl, gvor gvF? gv- gvANSWERS-I
In gvwhich gvreaction gvis gva gvracemic gvmixture gvobtained?
In gvwhich gvreaction gvis gvan gvinversion gvof gvchirality gvobtained? gv- gvANSWERS-
inversion: gvSn2
racemic gvmix: gvSn1
Cleavage gvof gvan gvether gvusually gvrequires gva gvstrong gvacid gvthat gvhas gva gvconjugate
gvbase gvwhich gvis gva gvstrong gvnucleophile, gvsuch gvas...? gvDepending gvon gvthe gvtype gvof
gvalkyl gvgroup, gvthe gvacid gvreaction gvwith gvthe gvhalide gvion gvproduces gvwhat? gv-
gvANSWERS-HBr
HI
alkyl gvhalide gvand gvan gvalcohol
When gvchirality gvrotates gvclockwise gvthe gvchirality gvis... gv- gvANSWERS-R
When gvchirality gvrotates gvcounterclockwise gvthe gvchirality gvis... gv- gvANSWERS-S
