ACS Organic Chemistry II Final
Examination questions and answers
What bis bthe bIUPAC bpriority bfor bnaming? b- bcorrect banswers✔✔Carboxylic bacid b>
bKetone b> bAldehyde b> bAlcohol
In bIUPAC bnaming, bwhat bis bthe bsuffix bused bfor bketone bgroups? b- bcorrect
banswers✔✔-one
In bIUPAC bnaming, bwhat bis bthe bsuffix bused bfor balcohol bgroups? b- bcorrect
banswers✔✔-nol
In bIUPAC bnaming, bwhat bis bthe bsuffix bused bfor besters? b- bcorrect banswers✔✔-noate
Benzyl bgroup b- bcorrect banswers✔✔
Phenyl bgroup b- bcorrect banswers✔✔
ethanoic bacid b- bcorrect banswers✔✔
(E) bisomers bvs. b(Z) bisomers. bWhich bone bis bobserved bwhen bthe bhigher branked
bmolecules bare bon bthe bsame bside? bopposite? b- bcorrect banswers✔✔highest bon
bsame bside: bZ
highest bon bopposite bsides: bE
Electron-withdrawing bgroups bare bwhat btype bof bdirectors? bWhat bis bthe bone band
bonly bexception? b- bcorrect banswers✔✔Meta b(deactivators) b
Halogens
If bthe batom bdirectly battached bto bthe baromatic bring bhas blone bpairs bwhat btype bof
bdirector bis bit? bwhat bif bit bdoes bnot bhave blone bpairs? b- bcorrect banswers✔✔lone
bpairs: bactivating, bortho, bpara bdirector
no blone bpairs: bdeactivating, bmeta bdirector
When bare bthe bterms bortho, bmeta, bpara bused? b- bcorrect banswers✔✔when bthere
bare b2 bsubstituents bon bthe baromatic bring
In bIUPAC bnaming, bwhat bis bNH2 bon ba bphenyl bring breferred bto bas? b- bcorrect
banswers✔✔aniline
, Analine b- bcorrect banswers✔✔
Amine b- bcorrect banswers✔✔
Amide b- bcorrect banswers✔✔
If bthere bis ba bNO2 bgroup bpresent, bwhat bIUPAC bprefix bwill balso bbe bevident? b-
bcorrect banswers✔✔nitro
What bis bthe bpredicted breaction? b1º balkyl bhalide bwith ba bstrong bbase? bweak bbase?
bpoor bnucleophile? b- bcorrect banswers✔✔strong bbase: bSn2 bfavored bbut bE2 bwith
bstrong bnon-nucleophilic bbases
weak bbase: bSn2
poor bnucleophile: bno breaction
What bis bthe bpredicted breaction? b2º balkyl bhalide bwith ba bstrong bbase? bweak bbase?
bpoor bnucleophile? b- bcorrect banswers✔✔strong bbase: bmostly bE2
strong bnon-nucleophilic bbases: bmostly bSn2
poor bnucleophile: bSn1/E2 b(slow) bin bpolar, bprotic bsolvents
What bis bthe bpredicted breaction? b3º balkyl bhalide bwith ba bstrong bbase? bweak bbase?
bpoor bnucleophile? b- bcorrect banswers✔✔strong bbase: bE2
strong bnon-nucleophilic bbases: bSn1/E1 bin bpolar bprotic bsolvents
poor bnucleophile: bSn1/E1 bin bpolar, bprotic bsolvents
What bis bthe bconfiguration bof bthe bproduct bin bthe bbase-catalyzed bhydrolysis bof b(R)-
1-choloro-1-deuteriobutane? b- bcorrect banswers✔✔(S)-1-deuterio-1-butanol b(Sn2)
Where bis bthe blargest bmolecule bon bthe bperiodic btable? b- bcorrect banswers✔✔Bottom
blefthand bcorner
Nucleophilic bstrength bincrease bwith bincreasing bwhat? b- bcorrect banswers✔✔atomic
bsize
Which balkyl bvalid bwould byou bexpect bto bundergo bSn1 bhydrolysis bmost brapidly?
I, bBr,Cl, bor bF? b- bcorrect banswers✔✔I
In bwhich breaction bis ba bracemic bmixture bobtained?
In bwhich breaction bis ban binversion bof bchirality bobtained? b- bcorrect
banswers✔✔inversion: bSn2
racemic bmix: bSn1
Cleavage bof ban bether busually brequires ba bstrong bacid bthat bhas ba bconjugate bbase
bwhich bis ba bstrong bnucleophile, bsuch bas...? bDepending bon bthe btype bof balkyl
bgroup, bthe bacid breaction bwith bthe bhalide bion bproduces bwhat? b- bcorrect
banswers✔✔HBr
Examination questions and answers
What bis bthe bIUPAC bpriority bfor bnaming? b- bcorrect banswers✔✔Carboxylic bacid b>
bKetone b> bAldehyde b> bAlcohol
In bIUPAC bnaming, bwhat bis bthe bsuffix bused bfor bketone bgroups? b- bcorrect
banswers✔✔-one
In bIUPAC bnaming, bwhat bis bthe bsuffix bused bfor balcohol bgroups? b- bcorrect
banswers✔✔-nol
In bIUPAC bnaming, bwhat bis bthe bsuffix bused bfor besters? b- bcorrect banswers✔✔-noate
Benzyl bgroup b- bcorrect banswers✔✔
Phenyl bgroup b- bcorrect banswers✔✔
ethanoic bacid b- bcorrect banswers✔✔
(E) bisomers bvs. b(Z) bisomers. bWhich bone bis bobserved bwhen bthe bhigher branked
bmolecules bare bon bthe bsame bside? bopposite? b- bcorrect banswers✔✔highest bon
bsame bside: bZ
highest bon bopposite bsides: bE
Electron-withdrawing bgroups bare bwhat btype bof bdirectors? bWhat bis bthe bone band
bonly bexception? b- bcorrect banswers✔✔Meta b(deactivators) b
Halogens
If bthe batom bdirectly battached bto bthe baromatic bring bhas blone bpairs bwhat btype bof
bdirector bis bit? bwhat bif bit bdoes bnot bhave blone bpairs? b- bcorrect banswers✔✔lone
bpairs: bactivating, bortho, bpara bdirector
no blone bpairs: bdeactivating, bmeta bdirector
When bare bthe bterms bortho, bmeta, bpara bused? b- bcorrect banswers✔✔when bthere
bare b2 bsubstituents bon bthe baromatic bring
In bIUPAC bnaming, bwhat bis bNH2 bon ba bphenyl bring breferred bto bas? b- bcorrect
banswers✔✔aniline
, Analine b- bcorrect banswers✔✔
Amine b- bcorrect banswers✔✔
Amide b- bcorrect banswers✔✔
If bthere bis ba bNO2 bgroup bpresent, bwhat bIUPAC bprefix bwill balso bbe bevident? b-
bcorrect banswers✔✔nitro
What bis bthe bpredicted breaction? b1º balkyl bhalide bwith ba bstrong bbase? bweak bbase?
bpoor bnucleophile? b- bcorrect banswers✔✔strong bbase: bSn2 bfavored bbut bE2 bwith
bstrong bnon-nucleophilic bbases
weak bbase: bSn2
poor bnucleophile: bno breaction
What bis bthe bpredicted breaction? b2º balkyl bhalide bwith ba bstrong bbase? bweak bbase?
bpoor bnucleophile? b- bcorrect banswers✔✔strong bbase: bmostly bE2
strong bnon-nucleophilic bbases: bmostly bSn2
poor bnucleophile: bSn1/E2 b(slow) bin bpolar, bprotic bsolvents
What bis bthe bpredicted breaction? b3º balkyl bhalide bwith ba bstrong bbase? bweak bbase?
bpoor bnucleophile? b- bcorrect banswers✔✔strong bbase: bE2
strong bnon-nucleophilic bbases: bSn1/E1 bin bpolar bprotic bsolvents
poor bnucleophile: bSn1/E1 bin bpolar, bprotic bsolvents
What bis bthe bconfiguration bof bthe bproduct bin bthe bbase-catalyzed bhydrolysis bof b(R)-
1-choloro-1-deuteriobutane? b- bcorrect banswers✔✔(S)-1-deuterio-1-butanol b(Sn2)
Where bis bthe blargest bmolecule bon bthe bperiodic btable? b- bcorrect banswers✔✔Bottom
blefthand bcorner
Nucleophilic bstrength bincrease bwith bincreasing bwhat? b- bcorrect banswers✔✔atomic
bsize
Which balkyl bvalid bwould byou bexpect bto bundergo bSn1 bhydrolysis bmost brapidly?
I, bBr,Cl, bor bF? b- bcorrect banswers✔✔I
In bwhich breaction bis ba bracemic bmixture bobtained?
In bwhich breaction bis ban binversion bof bchirality bobtained? b- bcorrect
banswers✔✔inversion: bSn2
racemic bmix: bSn1
Cleavage bof ban bether busually brequires ba bstrong bacid bthat bhas ba bconjugate bbase
bwhich bis ba bstrong bnucleophile, bsuch bas...? bDepending bon bthe btype bof balkyl
bgroup, bthe bacid breaction bwith bthe bhalide bion bproduces bwhat? b- bcorrect
banswers✔✔HBr
