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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) Nitrile with LiAlH4

Draw the product of the reaction of 2-phenylacetonitrile with lithium aluminium hydride.



(Enciphered hint 1: Sfevdujpo pg uif dzbop hspvq ublft qmbdf.)

3) 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.)

4) Pyrrolidine with HNO2

Draw the product of the reaction of pyrrolidine with sodium nitrite in the presence of hydrochloric acid.



(Enciphered hint 1: O-Ojusptbujpo ublft qmbdf.)

5) Butanal with NaBH4

Draw the product of the reaction of butanal with sodium borohydride followed by the reaction with water.



(Enciphered hint 1: Sfevdujpo pg uif pyp hspvq gpmmpxfe cz bo bdje-cbtf sfbdujpo pg uif gpsnfe bmlpyjef xjui xbufs.)

6) Pentano-5-lactone with methyl iodide

Draw the product of the following reaction of pentano-5-lactone.



(Enciphered hint 1: Bmlzmbujpo jo uif bmgb-qptjujpo pg uif ftufs hspvq.)

7) 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.)

8) D-Xylose with bromine

Draw the three-dimensional structure of the open-chain form of the product of the following reaction.



(Enciphered hint 1: Pyjebujpo pg uif dbscpozm hspvq ublft qmbdf. Bmepojd bdje jt gpsnfe.)

9) Acetone with dimethylamine

Draw the product of the reaction of acetone with dimethylamine.



(Enciphered hint 1: Bo fobnjof jt gpsnfe.)

10) 3-Methylcyclohex-2-en-1-one with phenylmethanethiol

Draw the product of the following reaction.



(Enciphered hint 1: Dpokvhbufe beejujpo.)

11) Methyl phenyl ketone with butylamine

Draw the product of the reaction of methyl phenyl ketone with butylamine.



(Enciphered hint 1: Beejujpo pg uif bnjof up uif dbscpozm hspvq sftvmujoh jo uif gpsnbujpo pg bo jnjof.)

12) Reduction of (E)-oct-2-en-4-yne

Draw the product of the reaction of (E)-oct-2-en-4-yne with hydrogen using the Lindlar catalyst. Consider the configuration of the product.



(Enciphered hint 1: Dpotjefs difnptfmfdujwjuz pg izesphfobujpo xjui uif Mjoembs dbubmztu.)

13) Maleinanhydride with buta-1,3-diene

Draw maleinanhydride and the product(s) of its reaction with buta-1,3-diene.


(Enciphered hint 1: Boizesjef pg ([)-cvufopjd bdje.)


(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

14) Reduction of L-glucononitrile

Draw the three-dimensional structure of the open-chain form of the product of the following reaction of L-glucononitrile.



(Enciphered hint 1: Sfevdujpo pg ojusjm up jnjof gpmmpxfe cz izespmztjt mfbejoh up bmefizef ublft qmbdf.)

15) Wittig reaction 2

Draw the product of the reaction of benzaldehyde with cyclopentylidenetriphenylphosphorane.



(Enciphered hint 1: Xjuujh sfbdujpo mfbet up bmlfoft.)

16) Cyclohexene with carbene

Draw the product of the following reaction.



(Enciphered hint 1: Dbscfof jt hfofsbufe boe uifo ju jt beefe up b epvcmf cpoe.)

17) Lactam with LiAlD4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo cz efvufsjef jpo ublft qmbdf.)

18) Haloform reaction 1

Draw all the organic products of the reaction of acetophenone (methyl phenyl ketone) with bromine in the presence of sodium hydroxide (after consequent acidification of the reaction).



(Enciphered hint 1: Evsjoh ibmpgpsn sfbdujpo, cspnjobujpo pg nfuizm hspvq gpmmpxfe cz dmfbwbhf pg uif cpoe cfuxffo uif dbscpozm hspvq boe uif bmgb dbscpo bupn.)

19) Kiliani-Fischer synthesis

What products would you expect from Kiliani-Fischer reaction of D-xylose? Draw the three-dimensional structure of their open-chain form.



(Enciphered hint 1: Uxp bmepifyptft ejggfsjoh jo uifjs tufsfpdifnjtusz bu D2 dbscpo.)

20) Hydroxymercuration of 1-methylcyclohexene

Draw the product of the following reaction.



(Enciphered hint 1: Bo bmdpipm jt gpsnfe bddpsejoh Nbslpwojlpw svmf.. )

21) D-Xylofuranose with acetic anhydride

Draw the three-dimensional structure of the product of the reaction of beta-D-xylofuranose with acetic anhydride in the presence of pyridine.



(Enciphered hint 1: Bmm uif -PI hspvqt sfbdu.)

22) 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.)

23) 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.)

24) Phenylisocyanate with 3-aminopropan-1-ol

Draw the product of the reaction of phenylisocyanate with 3-aminopropan-1-ol.



(Enciphered hint 1: Bnjoft bsf cfuufs ovdmfpqijmft uibo bmdpipmt.)

25) Phosgene with ethylamine

Fill the following scheme:



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf gpsnjoh bo vsfb. Uif bnjof fydftt jt ofdfttbsz up ofvusbmjaf gpsnjoh IDm.)

26) 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.)

27) Cyclohexyisothiocyanate with cyclohexylamine

Draw the product of the reaction of cyclohexyisothiocyanate with cyclohexylamine.



(Enciphered hint 1: Uif beejujpo pg ovdmfpqijmf up uif fmfduspqijmjd dbscpo ublft qmbdf.)

28) Aldolization - synthesis 1

Suggest the starting compounds for the preparation of the following product by aldol condensation.



(Enciphered hint 1: Tubsujoh dpnqpvoe dbo cf gpvoe cz jnbhjobsz ejtdpoofdujpo pg epvcmf cpoe.)

29) 4-Methylpent-3-en-2-on with nucleophile

Draw the product of the reaction of 4-methylpent-3-en-2-on with thiophenol in presence of base.



(Enciphered hint 1: 1,4-beejujpo.)

30) Diphenylketone and Beckmann rearangement

Diphenylketone reacts with hydroxylamine and the formed compound is treated under acid-catalyzed conditions. Draw the products of both reactions.



(Enciphered hint 1: Beejujpo pg izespyzmbnjof up dbscpozm hspvq.)



(Enciphered hint 1: Cfdlnboo sfbssbohfnfou. Bnjef jt gpsnfe.)

31) 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.)

32) 1-Bromo-1-methylcyklohexane with sodium ethoxide

Draw 1-bromo-1-methylcyklohexane and the major product of its reaction with sodium ethoxide.

(Enciphered hint 1: F2 fmjnjobujpo. B npsf tvctujuvufe epvcmf cpoe jt gpsnfe qsfgfsbcmz.)


(Enciphered hint 1: F2 fmjnjobujpo. B npsf tvctujuvufe epvcmf cpoe jt gpsnfe qsfgfsbcmz.)

33) 1-Bromopropane with potassium tert-butoxide

Draw the product of the following reaction.


(Enciphered hint 1: F2 fmjnjobujpo pddvst.)

34) Dehydrobromination of trans-2-bromo-1-methylcyclohexane

In scheme, trans-2-bromo-1-methylcyclohexane is drawn in the conformation suitable for E2 elimination by sodium ethanolate. Write major product of this reaction.


(Enciphered hint 1: F2 fmjnjobujpo qspdffejoh wjb bouj-nfdibojtn.)

35) p-Bromobenzyl bromide with sodium cyanide

Draw p-bromobenzyl bromide and the product of its reaction with sodium cyanide.

(Enciphered hint 1: 1-cspnp-4-(cspnpnfuizm)cfoafof)


(Enciphered hint 1: TO2 tvctujuvujpo pddvst)

36) Oxirane with methylmagnesium iodide

Draw the product of the following reaction.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

37) Butylmagnesium bromide with acetone

Draw the product of the reaction of butylmagnesium bromide with acetone and subsequent acidification.



(Enciphered hint 1: Uif gjstu sfbdujpo jt beejujpo pg b Hsjhobse sfbhfou up b dbscpozm hspvq.)


(Enciphered hint 1: Uif sfbdujpo pg uif bmlpyjef xjui ejmvuf bdje jt bo bdje-cbtf sfbdujpo.)

38) 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.)

39) Butylmagnesium bromide with ethanol

Draw the products of the reaction of butylmagnesium bromide with ethanol.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

40) 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.)

41) 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.)

42) Halogenation of acetone

Write enol form of acetone and the product of its reaction with bromine in acetic acid.


(Enciphered hint 1: Ubvupnfsjd gpsn pg bdfupof.)


(Enciphered hint 1: Fopm gpsn pg bdfupof voefshpft uif sfbdujpo xjui fmfduspqijmjd cspnjof.)


43) Propene with bromine

Draw the product of the following reaction.


(Enciphered hint 1: Fmfduspqijmjd cspnjobujpo pg b epvcmf cpoe.)

44) But-3-en-2-on with nucleophile

Draw the product of the reaction of but-3-en-2-on with lithium diethyl cuprate, followed by addition of water.



(Enciphered hint 1: 1,4-Beejujpo pg ovdmfpqijmf up bo bmgb, cfub-votbuvsbufe tztufn ublft qmbdf.)

45) Propanoic acid with ethanol

Draw the product of the reaction of propanoic acid with ethanol in the presence of sulfuric acid.



(Enciphered hint 1: Gjtdifs ftufsjgjdbujpo.)

46) 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.)

47) Preparation of ylide

Draw the product of the reaction of triphenylphosphine with ethyl bromide and the product of the successive reaction with butyllithium.



(Enciphered hint 1: Usjqifozmqiptqijof sfbdut bt ovdmfpqijmf.)


(Enciphered hint 1: Uif nptu bdjejd izesphfo jt mptu.)

48) Benzoic acid with oxalyl chloride

Draw the product of the reaction of benzoic acid with oxalyl chloride using N,N-dimethylformamide (DMF) as catalyst.



(Enciphered hint 1: Qsfqbsbujpo pg bdzm dimpsjef.)

49) Butanoic acid with bromine

Draw the product of the following reaction of butanoic acid.



(Enciphered hint 1: Bmqib ibmphfobujpo. Ifmm-Wpmibse-[fmjotlz sfbdujpo.)

50) Isopropylmagnesium bromide with CO2

Draw the product of the reaction of isopropylmagnesium bromide with carbon dioxide and subsequent acidification.



(Enciphered hint 1: Beejujpo pg uif Hsjhobse sfbhfou up uif dbscpo ejpyjef.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

51) 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.)

52) 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.)

53) Allyl bromide with sodium isopropoxide

Draw the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui jtpqspqpyjef bojpo bdujoh bt uif ovdmfpqijmf.)

54) Propanoic anhydride with water

Draw propanoic anhydride and the product of its reaction with water.


(Enciphered hint 1: Qspqbopjd bdje boizesjef.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

55) 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.)

56) 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.)

57) Butan-1-ol with hydrogen bromide

Draw the product of the reaction of butan-1-ol with hydrogen bromide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui cspnjef bojpo bdujoh bt uif ovdmfpqijmf. Bdjejd dpoejujpot bsf ofdfttbsz gps uif bdujwbujpo pg uif izespyz hspvq.)

58) Butanamide with bromine

Draw the carbon-containing products of the reaction of butanamide with bromine in the presence of sodium hydroxide.



(Enciphered hint 1: Ipgnboo sfbssbohfnfou.)

59) 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.)

60) 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.)

61) 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.)

62) Hexan-2-yl p-toluenesulfonate with sodium benzenthiolate

Draw three-dimensional formula of the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo qspdffejoh wjb TO2 nfdibojtn. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo.)

63) 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.)

64) 1-Methylcyclohexene with water under acidic conditions

Draw the product of the reaction of 1-methylcyclohexene with diluted sulfuric acid.


(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif nptu tubcmf dbscpdbujpo vqpo uif sfbdujpo xjui bo fmfduspqijmf (I+).)

65) Propene with bromine in water

Draw the product of the following reaction.


(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt hjwfo cz b qbsujbm qptjujwf dibshf po pof dbscpo bupn pg uif uisff-nfncfsfe sjoh pg b cspnpojvn dbujpo.)

66) 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.)

67) 2-Bromopentane with ethanol

Draw the three-dimensional structural formula of (S)-2-bromopentane and product(s) of its solvolysis in ethanol.




(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo qspdffejoh wjb TO1 nfdibojtn. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo.)

68) 2,2,3-Trimethyloxirane with methanol

Draw the major product of the following reaction.



(Enciphered hint 1: Usfbujoh b qspupobufe fqpyjef xjui ovdmfpqijmf mfbet up uif sjoh pqfojoh. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo. Qbz buufoujpo up uif sfhjptfmfdujwjuz pg uif sfbdujpo.)

69) Dieckmann condensation

Draw the products of the following reaction.



(Enciphered hint 1: Cfub-lfupftufs jt gpsnfe.)

70) Gabriel synthesis 2

The Gabriel synthesis is used for preparation of primary amines using potassium phthalimide. First draw the organic product of phthalimide alkylation by 3,5-dibromobenzyl bromide and then the products after reaction of the alkylated phthalimide with hydrazine.