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1) 1-Chloro-4-(trifluoromethyl)benzene with sodium methoxide

What product is formed by the reaction of 1-chloro-4-(trifluoromethyl)benzene with sodium methoxide in methanol?



(Enciphered hint 1: Usjgmvpspnfuizm hspvq bmmpxt ovdmfpqijmjd bspnbujd tvctujuvujpo up qspdffe tjnjmbsmz bt b ojusp hspvq.)

2) Bromination of anisole

Draw the product(s) of anisole (methyl phenyl ether) monobromination.



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo. Sfhjptfmfdujwjuz jt dpouspmmfe cz tvctujuvfou qsftfou po uif bspnbujd sjoh. )
(Enciphered hint 2: Nfuipyz hspvq jt p/q-ejsfdujoh.)

3) Nitrobenzene, substitution and reduction

Draw the product of nitrobenzene chlorination followed by hydrogenation on palladium.



(Enciphered hint 1: Fmfduspqijmjd tvctujuvujpo. Sfhjptfmfdujwjuz jt dpouspmmfe cz tvctujuvfou bmsfbez qsftfou po cfoafof sjoh.)


(Enciphered hint 1: Dbubmzujd izesphfobujpo.)

4) Mechanism of benzene nitration

Add structures into the mechanism of the nitration of benzene.



(Enciphered hint 1: Qptjujwfmz dibshfe opo-bspnbujd beevdu jt gpsnfe.)


(Enciphered hint 1: Bspnbujd dpnqpvoe jt gpsnfe.)

5) Acylium (2)

Draw the structure of the acylium ion formed from benzoyl chloride.



(Enciphered hint 1: Esbx pof pg uxp sftpobodf gpsnt pg bdzmjvn.)

6) Mechanism of electrophilic sulfonation

Add structures into the mechanism of the benzene sulfonation.



(Enciphered hint 1: Opo-bspnbujd qptjujwfmz dibshfe beevdu jt gpsnfe.)


(Enciphered hint 1: Bspnbujd qspevdu jt gpsnfe.)

7) Alkylation of anisole

Draw the product(s) of the following reaction.



(Enciphered hint 1: Bspnbujd fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Nfuipyz hspvq jt p/q-ejsfdujoh.)

8) Bromination of acetanilide

Draw acetanilide and the major product of its bromination. Consider monobromination.


(Enciphered hint 1: O-qifozmbdfubnjef.)


(Enciphered hint 1: Dpotjefs cpui fmfduspojd boe tufsjd fggfdut.)

9) Bromination of anisole - intermediate

Draw the most stable resonance form of cyclohexadienyl carbocation which is the intermediate of anisole (phenyl methyl ether) bromination.



(Enciphered hint 1: Dbscpdbujpo (tjhnb-dpnqmfy) jt gpsnfe cz uif sfbdujpo pg bsfof xjui bo fmfduspqijmf.)

10) Bromination of nitrobeneze - intermediate

Draw the structure of two resonance forms of the cyclohexadienyl carbocation which is the intermediate of nitrobenzene bromination.



(Enciphered hint 1: Dbscpdbujpo (tjhnb-dpnqmfy) jt gpsnfe cz uif sfbdujpo pg bsfof xjui bo fmfduspqijmf.)
(Enciphered hint 2: Esbx uxp pg uif Uisff sftpobodf gpsnt.)

11) Dichlorobenzene with nitric acid and then with ammonia

What product is formed by the reaction of 1,3-dichlorobenzene with a mixture of nitric and sulfuric acids (consider the major product), and then with ammonia in ethylene glycol?



(Enciphered hint 1: Bmtp tufsjd ijoesbodf qmbzt spmf evsjoh fmfdupqijmjd tvctujuvujpo.)


(Enciphered hint 1: B njyuvsf pg uxp qspevdut jt gpsnfe.)

12) Diazonium salt with N,N-dimethylaniline

Draw the product of the reaction of 4-nitrobenzenediazonium bisulfate with N,N-dimethylaniline.



(Enciphered hint 1: B ejbapojvn dpvqmjoh sfbdujpo ublft qmbdf.)

13) Nitroso compounds (5)

Draw the product of the reaction of N,N-dimethylaniline with sodium nitrite in the presence of hydrochloric acid.



(Enciphered hint 1: Ojusptp hspvq jt jouspevdfe po uif bspnbujd sjoh.)

14) Bromination of 1-methylnaphtalene

Draw the product(s) of 1-methylnaphthalene monobromination.



(Enciphered hint 1: B njyuvsf pg uxp qspevdut jt gpsnfe (cspnjobujpo po uif bdujwbufe sjoh).)

15) Sulfonation of naphthalene

Draw the product of the sulfonation of naphthalene at 80 °C.



(Enciphered hint 1: Ljofujdbmmz dpouspmmfe sfbdujpo.)

16) Acylium (3)

Draw the structure of the acylium ion formed from acetic anhydride.



(Enciphered hint 1: Bdfuzm dimpsjef hjwft bdzmjvn pg uif tbnf tusvduvsf.)

17) Furan with pyridine sulfur trioxide complex

Draw furan and the product of its monosulfonation.


(Enciphered hint 1: Gjwf-nfncfsfe pyzhfo dpoubjojoh ifufspbspnbujd dpnqpvoe.)


(Enciphered hint 1: Fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz fotvft gspn uif gpsnbujpo pg b tubcjmjafe dbscpdbujpo evsjoh uif sfbdujpo xjui bo fmfduspqijmf.)
(Enciphered hint 2: D-T cpoe jt gpsnfe cz tvmgpozmbujpo.)

18) Pyrrole with acetyl nitrate

Draw the product of the reaction of pyrrole with acetyl nitrate.



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo ublft qmbdf.)

19) Thiophene with sulfuric acid

Draw thiophene and the product of its reaction with concentrated sulfuric acid.


(Enciphered hint 1: Uijpqifof jt b gjwf-nfncfsfe bspnbujd ifufspdzdmjd dpnqpvoe dpoubjojoh pof tvmgvs bupn.)


(Enciphered hint 1: Npop-tvmgpobujpo pddvst.)

20) Chlorination of nitrobenzene

Draw the product of the following reaction.



(Enciphered hint 1: Bspnbujd fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Ojusp hspvq ejsfdu tvctujuvujpo jo qptjujpo nfub.)

21) Nitration of nitronaphthalene

Draw the product of the following reaction.



(Enciphered hint 1: Uxp qsfwbjmjoh qspevdut bsf gpsnfe cz ojusbujpo pg npsf sfbdujwf bspnbujd sjoh.)

22) Acetylation of toluene

Draw the product(s) of the following reaction.



(Enciphered hint 1: Bspnbujd fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)

23) Sulfonation of naphthalene (2)

Draw the product of the sulfonation of naphthalene at 160 °C.



(Enciphered hint 1: Uifsnpezobnjdbmmz dpouspmmfe sfbdujpo.)

24) Acetylation of benzene

Draw the product of the following reaction.



(Enciphered hint 1: Bdzmbujpo ubljoh qmbdf cz fmfduspqijmjd bspnbujd tvctujuvujpo.)

25) Pyridine with bromine

Draw pyridine and the product of its monobromination.


(Enciphered hint 1: Qzsjejof jt b tjy-nfncfsfe ifufspbspnbujd dpnqpvoe dpoubjojoh b ojusphfo bupn.)


(Enciphered hint 1: Fmfduspqijmjd tvctujuvujpo. Uif tvctujuvfou jt ejsfdufe up qptjujpo 3 pg uif qzsjejof sjoh.)

26) Thiophene with acetyl chloride

Draw the product of the reaction of thiophene with acetyl chloride in the presence of aluminium trichloride.



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo ublft qmbdf. Ublf dbssf bcpvu sfhjptfmfdujwjuz.)

27) Quinoline with HNO3/H2SO4

Draw the products of the reaction of quinoline with the mixture of nitric acid and sulfuric acid.



(Enciphered hint 1: Ojusbujpo ublft qmbdf po npsf bdujwbufe sjoh.)

28) Bromobenzene with pentyl chloride

Draw the organic products of the following reaction:



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo. Uif fmfduspqijmf jt b tfdpoebsz dbscpdbujpo gpsnfe cz uif sfbdujpo pg bmlzm ibmjef xjui Mfxjt bdje.)
(Enciphered hint 2: Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)

29) Bromination of aniline

Draw aniline and the product of its tribromination.


(Enciphered hint 1: Usjwjbm obnf gps cfoafof bnjof)


(Enciphered hint 1: Bnjop hspvq jt bo p/q ejsfdujoh hspvq.)

30) Mechanism of Friedel-Crafts alkylation

Draw the structure of the electrophile formed in the reaction of benzene with propene in the presence of acidic catalyst. Then, draw the intermediate and product of the reaction.



(Enciphered hint 1: Npsf tubcmf dbscpdbujpo bdut bt fmfduspgjmf.)


(Enciphered hint 1: Qptjujwfmz dibshfe opo-bspnbujd beevdu jt gpsnfe.)


(Enciphered hint 1: Bspnbujd qspevdu jt gpsnfe.)

31) Nitration of 4-chlorobenzoic acid

Draw 4-chlorobenzoic acid and the major product of its nitration.


(Enciphered hint 1: Bspnbujd bdje.)


(Enciphered hint 1: Bspnbujd fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfout qsftfou po uif bspnbujd sjoh.)

32) Acetylation of anisole

Draw the product(s) of Friedel-Crafts acetylation of methyl phenyl ether (anisole). Consider monoacetylation only.



(Enciphered hint 1: Bspnbujd fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Nfuipyz hspvq jt psuip/qbsb-ejsfdujoh.)

33) Quinoline with bromine

Draw the products of the reaction of quinoline with bromine in sulfuric acid in the presence of silver sulfate.



(Enciphered hint 1: Uif fmfduspqijmjd bspnbujd tvctujuvujpo pg npsf sfbdujwf sjoh ublft qmbdf.)
(Enciphered hint 2: Uxp qspevdut pg uif sfbdujpo bsf gpsnfe.)

34) Nitration of acetophenone

Draw the product of the following reaction.



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Bdfuzm jt b nfub ejsfdujoh hspvq.)

35) Pyrrole - electrophilic substitution

Draw three resonance structures which support the hypothesis of electrophilic bromination proceeding at position two of the pyrrole ring.



(Enciphered hint 1: Uif dbujpo gpsnfe dbo cf ejtqmbzfe vtjoh uisff sftpobodf gpsnt.)

36) Nitration of anisole - intermediate

Draw the structure of two resonance forms of the cyclohexadienyl carbocation which is the intermediate of anisole (methyl phenyl ether) nitration into para-position.



(Enciphered hint 1: Dbscpdbujpo (tjhnb-dpnqmfy) jt gpsnfe cz uif sfbdujpo pg bsfof xjui bo fmfduspqijmf.)
(Enciphered hint 2: Esbx uxp pg uif uisff qpttjcmf sftpobodf gpsnt.)

37) Synthesis of n-alkyl arene (1)

One method to synthesize n-alkyl arenes involves acylation followed by reduction of the formed ketone. This approach avoids carbocation rearrangement occuring during alkylation. Draw the products of the following schemes:



(Enciphered hint 1: Gsjfem-Dsbgut bdzmbujpo. B lfupof jt gpsnfe.)


(Enciphered hint 1: Sfevdujpo pg lfupof up nfuizmfof.)

38) Benzene with propionic anhydride

Draw all organic products of the following reaction:



(Enciphered hint 1: Gsjfefm-Dsbgut bdzmbujpo.)

39) Structure of a sigma complex

Draw two resonance structures of the cation in the picture. The cation is an intermediate of toluene nitration.



(Enciphered hint 1: Tjhnb dpnqmfy jt b dbscpdbujpo gpsnfe cz uif sfbdujpo pg bsfof xjui fmfduspqijmf evsjoh fmfduspqijmjd bspnbujd tvctujuvujpo.)

40) Sulfonation of toluene

Draw the product(s) of toluene sulfonation. Consider monosulfonation only.



(Enciphered hint 1: Bspnbujd fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Tvmgpozm hspvq jt jouspevdfe cz tvmgpozmbujpo. D-T cpoe jt gpsnfe.)

41) Bromination of (trifluoromethyl)benzene

Draw the product of the following reaction.



(Enciphered hint 1: Bspnbujd fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Usjgmvpspnfuizm jt b nfub-ejsfdujoh hspvq.)

42) Nitration of nitrotoluene

Draw the product of nitration of 4-nitrotoluene.



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Sfbdujpo jt dpouspmmfe cz p/q-ejsfdujoh hspvq.)

43) Bromination of toluene - intermediate

Draw the most stable resonance form of cyclohexadienyl carbocation which is the intermediate of toluene (methylbenzene) bromination.



(Enciphered hint 1: Dbscpdbujpo (tjhnb-dpnqmfy) jt gpsnfe cz uif sfbdujpo pg bsfof xjui bo fmfduspqijmf.)

44) Acylium

Draw the structure of the acylium ion formed from propanoyl chloride.



(Enciphered hint 1: Bdzmjvn jpot bsf joufsnfejbuft pg Gsjfefm-Dsbgut bdzmbujpot.)
(Enciphered hint 2: Esbx pof pg uif uxp sftpobodf gpsnt.)

45) Pyridine and pyridine N-oxide under nitration

Draw the products of the reactions of pyridine and pyridine N-oxide under nitration conditions:



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo up uif qptjujpo 3 ublft qmbdf.)


(Enciphered hint 1: Ojusbujpo pg qzsjejof O-pyjef ublft qmbdf bu uif qptjujpo 4.)

46) Dioxane dibromide

Bromination reactions of furan and pyrrole require mild reaction conditions; therefore dioxane dibromide is used as a bromination reagent. Draw its structure.


(Enciphered hint 1: Ju jt uif beevdu gpsnfe gspn uif Mfxjt cbtf ejpybof boe uif Mfxjt bdje cspnjof.)

47) Pyridine sulfur trioxide complex

Sulfonation reactions of furan and pyrrole require mild reaction conditions; therefore, pyridine sulfur trioxide complex is used as a reagent. Draw its structure.


(Enciphered hint 1: Ju jt uif beevdu gpsnfe gspn uif Mfxjt cbtf qzsjejof boe uif Mfxjt bdje tvmgvs usjpyjef.)

48) Benzene with butene

Draw the major product of the following reaction:



(Enciphered hint 1: Ju jt bo fmfduspqijmjd bspnbujd tvctujuvujpo sfbdujpo. Uif fmfduspqijmf jt uif npsf tubcmf (tfdpoebsz) dbscpdbujpo gpsnfe cz uif sfbdujpo pg cvufof voefs bdjejd dpoejujpot.)

49) Toluene with cyclohexanol

Draw the major product of the following reaction:



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo. Uif fmfduspqijmf jt b tfdpoebsz dbscpdbujpo gpsnfe cz uif qspupobujpo pg uif bmdpipm.)
(Enciphered hint 2: Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh. Evf up uif tufsjd efnboet pg cpui uif tvctujuvfout, uif qbsb-ejtvctujuvufe qspevdu jt uif nbkps pof.)

50) Pyridine with HNO3/H2SO4

Draw pyridine and the product of its mononitration.


(Enciphered hint 1: B tjy-nfncfsfe ifufspbspnbujd dpnqpvoe xjui b ojusphfo bupn.)


(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo up qptjujpo 3.)

51) Toluene with succinic anhydride

Draw the major organic product of the following reaction:



(Enciphered hint 1: Gsjfefm-Dsbgut bdzmbujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Uif gpsnfe bdje epft opu sfbdu xjui bmvnjojvn(JJJ) dimpsjef up gpsn b ofx fmfduspqijmf; uifsfgpsf, uif pypbdje jt uif qspevdu.)

52) Iodobenzene with phthalic anhydride

Draw the major organic product of the following reaction:



(Enciphered hint 1: Gsjfefm-Dsbgut bdzmbujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh.)
(Enciphered hint 2: Uif gpsnfe bdje epft opu sfbdu xjui bmvnjojvn(JJJ) dimpsjef up gpsn b ofx fmfduspqijmf; uifsfgpsf, uif pypbdje jt uif qspevdu.)

53) Iodobenzene with cycloheptene

Draw the major product of the following reaction:



(Enciphered hint 1: Ju jt bo fmfduspqijmjd bspnbujd tvctujuvujpo sfbdujpo. Uif fmfduspqijmf jt b tfdpoebsz dbscpdbujpo gpsnfe cz uif qspupobujpo pg uif D=D cpoe.)
(Enciphered hint 2: Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif tvctujuvfou qsftfou po uif bspnbujd sjoh. Evf up uif tufsjd efnboet pg cpui uif tvctujuvfout, uif qbsb-ejtvctujuvufe qspevdu jt uif nbkps pof.)

54) Benzene with pentanol

Draw the major product of the following reaction:



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo. Uif fmfduspqijmf jt b tfdpoebsz dbscpdbujpo gpsnfe cz uif qspupobujpo pg uif bmdpipm.)

55) Furan with dioxan dibromide

Draw the structure of the product of the reaction of furan with dioxane dibromide.



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo ublft qmbdf.)

56) Indole with dioxane dibromide

Draw the product of the reaction of indole with dioxane dibromide.



(Enciphered hint 1: Fmfduspqijmjd tvctujuvujpo.)

57) Benzene with succinic anhydride

Draw the organic product of the following reaction:



(Enciphered hint 1: Gsjfefm-Dsbgut bdzmbujpo.)
(Enciphered hint 2: Uif gpsnfe bdje epft opu sfbdu xjui bmvnjojvn(JJJ) dimpsjef up gpsn b ofx fmfduspqijmf; uifsfgpsf, uif pypbdje jt uif qspevdu.)

58) Nitration of acetophenone - intermediate

Draw the structure of two resonance forms of the cyclohexadienyl carbocation which is the intermediate of acetophenone nitration.



(Enciphered hint 1: Dbscpdbujpo (tjhnb-dpnqmfy) jt gpsnfe cz uif sfbdujpo pg bsfof xjui bo fmfduspqijmf.)
(Enciphered hint 2: Esbx uxp pg uif uisff qpttjcmf sftpobodf gpsnt.)