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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) Benzaldehyde with peracid

Benzaldehyde can be used to synthesize phenol. Fill in the following schemes:



(Enciphered hint 1: Cbfzfs-Wjmmjhfs pyjebujpo.)


(Enciphered hint 1: Izespmztjt pg bo ftufs.)

3) Reduction of benzene

A radical anion is formed as an intermediate in the reaction of benzene with sodium in liquid ammonia and methanol. It is then protonized. Draw the structure of the radical anion and then of the radical intermediates.



(Enciphered hint 1: Sbejdbm boe fmfduspo qbjs bsf mpdbmjafe jo uif qptjujpot 1 boe 4.)


(Enciphered hint 1: Qspupobujpo cz nfuibopm.)

4) 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.)

5) Bromination of propylbenzene with NBS

Draw the product of the bromination of propylbenzene with N-bromosuccinimide.



(Enciphered hint 1: Sbejdbm cspnjobujpo pg uif tjef dibjo. Gjoe uif nptu tubcmf sbejdbm.)

6) 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.)

7) 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.)

8) Acylium (2)

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



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

9) 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.)

10) 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.)

11) 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.)

12) 2,4,6-Trinitrochlorobenzene with hydroxide

Draw the product of the reaction of 2,4,6-trinitrochlorobenzene with hydroxide anion.



(Enciphered hint 1: Ovdmfpqijmjd bspnbujd tvctujuvujpo.)

13) p-Isopropyltoluene with sodium dichromate

Draw the product of the reaction of 1-isopropyl-4-methylbenzene with sodium dichromate.



(Enciphered hint 1: Pyjebujpo pddvst jo uif tjef dibjo pg uif bspnbujd sjoh.)

14) 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.)

15) Benzyne - Diels-Alder reaction

When furan is added to the mixture of bromobenzene and potassium amide, benzyne  intermediate is trapped by furane under formation 4+2 cycloadduct. Draw structures of benzyne and 4+2 cycloadduct.



(Enciphered hint 1: Bu gjstu, fmjnjobujpo ublft qmbdf.)


(Enciphered hint 1: Gvsbo tfswft bt b usbq up dbquvsf uif joufsnfejbuf - cfoazof. Gvsbo jt b ejfof, cfoazof jt b ejfopqijmf.)

16) 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.)

17) 2,6-Dideuteriochlorobenzene with sodium amide

What products are formed by the reaction of 2,6-dideuteriochlorobenzene with sodium amide in ammonia. First, draw the reactive intermediate and then product(s) of the reaction.



(Enciphered hint 1: Fmjnjobujpo ublft qmbdf bggpsejoh bszof.)


(Enciphered hint 1: Uxp qspevdut bsf gpsnfe cz sfbdujpo pg opo-tznnfusjdbm bszof xjui b ovdmfpqijmf.)

18) 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.)

19) Substitution reactions on 1-chloro-4-methoxy-2-methylbenzene

What product is formed by the reaction of 4-methoxy-2-methylchlorobenzene with N-bromosuccinimide in CCl4 and the presence of organic peroxides and then with sodium methanethiolate? The molecular formula of the final product is C9H11BrOS



(Enciphered hint 1: Gjstu, sbejdbm tvctujuvujpo pddvst.)


(Enciphered hint 1: Uifo ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

20) Rate of nucleophilic substitution

From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C.



(Enciphered hint 1: B ojusp hspvq gbdjmjubuft ovdmfpqijmjd bspnbujd tvctujuvujpo pomz jo qptjujpot psuip boe qbsb.)

21) Nucleophilic substitution rate in halonitrobenzenes

From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C.



(Enciphered hint 1: Uif sfbdujwjuz pg ibmpcfoafoft jo ovdmfpqijmjd bspnbujd tvctujuvujpo efdsfbtft jo psefs G>Dm>Cs.)

22) Anisole with sodium

Anisole (methyl phenyl ether) undergoes Birch reduction by sodium in liquid ammonia. Draw the product of the reaction.



(Enciphered hint 1: Uxp-fmfduspo sfevdujpo pg bspnbujd sjoh.)
(Enciphered hint 2: Tvctujuvfout xjui N+ mfbe up uif qspevdut xjui uif nptu ijhimz tvctujuvufe epvcmf cpoet, j.f. uif hspvq jt po uif epvcmf cpoe.)


23) 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.)

24) 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).)

25) Sulfonation of naphthalene

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



(Enciphered hint 1: Ljofujdbmmz dpouspmmfe sfbdujpo.)

26) Acylium (3)

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



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

27) Diazonium salt with CuCl

Draw the product of the reaction of 3-methylbenzenediazonium chloride with copper(I) chloride.



(Enciphered hint 1: Tvctujuvujpo pg uif ejbap hspvq ublft qmbdf.)

28) Aromaticity (1)

From the following compounds choose those that are aromatic.



(Enciphered hint 1: Qmbobs tztufnt xjui 4o+2 dpokvhbufe qj-fmfduspot (Iv̈dlfm't svmf).)

29) 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.)

30) p-Bromotoluene with sodium hydroxide

A mixture of two products is formed by the reaction of p-bromotoluene with sodium hydroxide. Draw the unstable intermediate and then the final products.



(Enciphered hint 1: Uif sfbdujpo qspdffet wjb fmjnjobujpo-beejujpo nfdibojtnt xjui bo bszof cfjoh bo joufsnfejbuf.)


(Enciphered hint 1: Uif sfbdujpo pg opo-tznnfusjdbm bszof xjui b ovdmfpqijmf bggpset uxp qspevdut.)

31) Chloronitrobenzene with thiolate

What product is formed by the reaction of 1-chloro-4-methyl-2-nitrobenzene with potassium benzylthiolate?



(Enciphered hint 1: Bspnbujd ovdmfpqijmjd tvctujuvujpo qspdffejoh cz beejujpo-fmjnjobujpo nfdibojtn.)

32) Rate of nucleophilic substitution in halonitrobenzenes.

From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C.



(Enciphered hint 1: B ojusp hspvq gbdjmjubuft ovdmfpqijmjd bspnbujd tvctujuvujpo jo psuip boe qbsb qptjujpo.)

33) Aromaticity (2)

From the following compounds choose those do not behave as aromatic compounds.



(Enciphered hint 1: Qmbobs tuvduvsft xjui 4o+2 qj-fmfduspot (Iv̈dlfm't svmf). Uif svmf xbt psjhjobmz efgjofe gps npopdzdmjd dpnqpvoet. Ofwfsuifmftt uifsf bsf npsf dpnqmfy tusvduvsft xijdi cfibwf mjlf bspnbujdt.)

34) Nitroso compounds (6)

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



(Enciphered hint 1: Ojusptbujpo pg uif tfdpoebsz bnjop hspvq.)

35) 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.)

36) 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.)

37) Sulfonation of naphthalene (2)

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



(Enciphered hint 1: Uifsnpezobnjdbmmz dpouspmmfe sfbdujpo.)

38) Benzoic acid with sodium

Benzoic acid undergoes Birch reduction by sodium in liquid ammonia. Draw the product of the reaction.



(Enciphered hint 1: Uxp-fmfduspo sfevdujpo pg bspnbujd sjoh.)
(Enciphered hint 2: Tvctujuvfout xjui N- mfbe up uif qspevdut ibwjoh uif tvctujuvfou dpoofdufe up uif dbscpo bupn xjui tq3 izcsjejabujpo.)


39) Acetylation of benzene

Draw the product of the following reaction.



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

40) 2-Methylpropene under acidic conditions

Draw structure of carbocation formed primarily by the reaction of 2-methylpropene with aqueous sulphuric acid.



(Enciphered hint 1: Npsf tubcmf dbscpdbujpo jt gpsnfe.)

41) 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.)

42) Aryl ester with aluminium(III) chloride

Draw the product of heating of phenyl propanoate with aluminium(III) chloride:



(Enciphered hint 1: Gsjft sfbssbohfnfou.)

43) Reaction of benzenesulfonic acid

Draw the product of the reaction of benzenesulfonic acid with sodium hydroxide at 300 °C.



(Enciphered hint 1: Uif sfqmbdfnfou pg uif -TP3I hspvq ublft qmbdf.)

44) Diazonium salt with Cu2O/Cu(NO3)2

Draw the product of the following reaction of 2-methyl-5-nitroaniline.



(Enciphered hint 1: B ejbapojvn tbmu jt uif joufsnfejbuf.)

45) Diazonium salt with CuBr

Draw the product of the reaction of 2-methylbenzenediazonium bromide with copper(I) bromide.



(Enciphered hint 1: Tvctujuvujpo pg uif ejbap hspvq ublft qmbdf.)

46) 2,3-Dimethylnaphthalene with Na2Cr2O7

Draw the product of the reaction of 2,3-dimethylnaphthalene with sodium dichromate.



(Enciphered hint 1: Pyjebujpo pg nfuizm hspvqt dpoofdufe up uif bspnbujd sjoh ublft qmbdf.)

47) Structure to name (20)

Name the following structure:



(Enciphered hint 1: Ju jt b ejbmlpyz efsjwbuf.)

48) 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.)

49) 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.)

50) Structure of a Meisenheimer complex of chloro nitro benzene with methanolate

Draw the structure of the Meisenheimer complex which is the intermediate of the following reaction.



(Enciphered hint 1: Uif sfbdujpo jt b ovdmfpqijmjd bspnbujd tvctujuvujpo qspdffejoh cz bo beejujpo-fmjnjobujpo nfdibojtn. Nfjtfoifjnfs dpnqmfy jt gpsnfe cz uif beejujpo pg b ovdmfpqijmf po uif dbscpo bupn cfbsjoh uif mfbwjoh hspvq.)

51) Synthesis of chlorobenside

The preparation of the pesticide chlorobenside is composed of several steps. The first step is the reaction of 1-(chloromethyl)-4-nitrobenzene with 4-chloro benzenethiolate anion. Draw product of the reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo.)

Now the sulfide reacts with iron in HCl and then with NaOH.



(Enciphered hint 1: Ojusp hspvq sfevdujpo.)

52) 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.)

53) 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.)

54) 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.)

55) 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.)

56) 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.)

57) Benzene with propionic anhydride

Draw all organic products of the following reaction:



(Enciphered hint 1: Gsjfefm-Dsbgut bdzmbujpo.)

58) Chloronitrobenzenes - reaction with nucleophiles

From the following structures choose the ones which can undergo a substitution of chlorine atom with hydroxide anion.



(Enciphered hint 1: Ojusp hspvq qspwjeft ovdmfpqijmjd bspnbujd tvctujuvujpo cz sftpobodf fggfdu xijdi jt opu qpttjcmf jo b nfub qptjujpo.)

59) 1-Chloroanthraquinone with methoxide anion

1-Chloroanthraquinone reacts with methoxide anion. Draw the structure of a Meisenheimer complex and the final product.



(Enciphered hint 1: Nfjtfoifjnfs dpnqmfy jt gpsnfe cz beejujpo pg b ovdmfpqijmf boe ju jt tubcjmjafe cz sftpobodf.)

(Enciphered hint 1: Bspnbujd ovdmfpqijmjd tvctujuvujpo.)

60) Chlorobenzene - aromatic substitution

Chlorobenzene usually does not react with nucleophiles. However, at high temperatures and high pressure phenol is formed by the reaction with water. Reaction takes place by an elimination-addition mechanism. First, draw the product of elimination and then the product of the addition of water to the unstable intermediate.



(Enciphered hint 1: Cfoazof jt gpsnfe.)


(Enciphered hint 1: Qspevdu jt gpsnfe cz beejujpo pg b ovdmfpqijmf up cfoazof.)

61) 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.)

62) Aromaticity 3

From the following compounds choose those which behave as aromatic compounds.



(Enciphered hint 1: Qmbobs tztufnt xjui 4o+2 dpokvhbufe qj-fmfduspot (Iv̈dlfm't svmf).)

63) 1-Chloro-4-nitrobenzene with methylamine

Draw the product of the following reaction.


(Enciphered hint 1: Ovdmfpqijmjd bspnbujd tvctujuvujpo qspdffejoh cz beejujpo-fmjnjobujpo nfdibojtn.)

64) Dichloro-nitrobenzene with hydroxide

Draw the product of the reaction of 1,2-dichloro-4-nitrobenzene with hydroxide anion.



(Enciphered hint 1: Ojusp hspvq qspwjeft ovdmfpqijmjd bspnbujd tvctujuvujpo cz sftpobodf fggfdu xijdi jogmvfodft uif sfbdujwjuz pomz jo psuip ps qbsb qptjujpo.)

65) Aniline with HNO2

Draw the product of the following reaction.



(Enciphered hint 1: B ejbapojvn tbmu jt gpsnfe.)

66) Diazonium salt with HBF4

Draw the product of the following reaction.