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1) 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.)

2) 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.)

3) Dopamine

Draw the structure of 4-(2-aminoethyl)benzene-1,2-diol.


(Enciphered hint 1: 2-Bnjopfuizm nfbot -DI2DI2OI2 hspvq.)

4) Acetone with dimethylamine

Draw the product of the reaction of acetone with dimethylamine.



(Enciphered hint 1: Bo fobnjof jt gpsnfe.)

5) 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.)

6) Reductive amination 4

Draw the starting compounds which produce the tertiary amine shown bellow on reductive amination.



(Enciphered hint 1: B dbscpozm dpnqpvoe boe bo bnjof bsf offefe.)

7) 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.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo. Bo bnjof boe b izesbajef bsf gpsnfe.)

8) Benzophenone with O-methylhydroxylamine

Draw the product of the reaction of benzophenone with O-methylhydroxylamine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet jo uif gjstu tufq up b hfnjobm bnjop bmdpipm. Tvctfrvfou xbufs fmjnjobujpo hjwft bo pyjnf.)

9) 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.)

10) 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.)

11) Benzaldehyde with aniline

Draw the product of the reaction of benzaldehyde with aniline.



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

12) Enantiomer 2

Draw a three-dimensional structural formula of the enantiomer of the given compound.



(Enciphered hint 1: Bo foboujpnfs ibt uif pqqptjuf dpogjhvsbujpo po bmm uif tufsfphfojd dfousft.)

13) 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.)

14) Edrophonium chloride

Draw the structure of N-ethyl-3-hydroxy-N,N-dimethylbenzenammonium chloride.


(Enciphered hint 1: Rvbsufsobsz bnnpojvn tbmu.)

15) Nitroso compounds 4

Propan-2-amine reacts with sodium nitrite in the presence of hydrochloric acid under formation of an unstable salt which decomposes. Draw structures of the salt and the decomposition product.



(Enciphered hint 1: Ejbapojvn tbmu jt gpsnfe.)


(Enciphered hint 1: B dbscpdbujpo jt gpsnfe boe ju voefshpft sfbdujpo xjui b ovdmfpqijmf.)

16) Amide with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

17) 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.)

18) Order of basicity (3)

Choose the least basic heterocyclic compound.



(Enciphered hint 1: Uif cbtjdjuz jt jogmvfodfe cz dpokvhbujpo pg uif mpof fmfduspo qbjs joup uif bspnbujd tztufn.)

19) Cope elimination

Draw the products of the thermal cleavage of the following N-oxide.



(Enciphered hint 1: Fmjnjobujpo ublft qmbdf. Bo bmlfof jt gpsnfe.)

20) Cyclohexanone with isobutylamine

Draw the product of the reaction of cyclohexanone with isobutylamine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf gpsnjoh bo jnjof.)

21) 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.)

22) Reductive amination 2

Draw the product of the reaction of cyclohexanone with ethylamine in the presence of sodium cyanoborohydride.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up bo jnjof, xijdi jt uifo sfevdfe cz uif bdujpo pg tpejvn dzbopcpspizesjef.)

23) 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.)

24) Pyridine-3-carboxaldehyde with 2,4-dinitrophenylhydrazine

Draw the product of the reaction of pyridine-3-carboxaldehyde with 2,4-dinitrophenylhydrazine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf.)

25) Diisopropylamine with butyllithium

Draw the products of the reaction of diisopropylamine with butyllithium.



(Enciphered hint 1: B tbmu boe bo bmlbof bsf gpsnfe.)

26) Azide with LiAlH4

Draw the product of the reaction of 3-phenylpropyl azide with lithium aluminium hydride.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

27) Dimethylamine with HNO2

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



(Enciphered hint 1: Ojusptbujpo ublft qmbdf.)

28) Cyclohexanone with hydrazine

Draw the product of the reaction of cyclohexanone with hydrazine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf.)

29) Aniline with HNO2

Draw the product of the following reaction.



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

30) Diazonium salt with HBF4

Draw the product of the following reaction.



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

31) Diazonium salt with KI

Draw the product of the reaction of benzenediazonium chloride with potassium iodide.



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

32) Diazonium salt with CuCN

Draw the product of the reaction of 4-isopropylbenzenediazonium bisulfate with copper(I) cyanide.



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

33) Hofmann elimination

Draw the major product of the following reaction.



(Enciphered hint 1: Mftt-tvctujuvufe bmlfof jt gpsnfe.)

34) Hofmann rearrangement - mechanism

Draw the structure of the isocyanate, that is the key intermediate in the Hofmann rearrangement of pentanamide.



(Enciphered hint 1: Bo bmlzm buubdife up uif dbscpozm hspvq njhsbuft up ojusphfo.)

35) Acetophenone with morpholine

Draw the product of the reaction of acetophenone with morpholine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up bo jojujbm beevdu (hfnjobm bnjop bmdpipm), xijdi bgufs efizesbujpo zjfmet bo fobnjof.)

36) Diastereomer 3

Draw three-dimensional structural formula of the diastereomer of cyclohexan-1,2-diamine.



(Enciphered hint 1: B ejbtufsfpnfs jt b tufsfpjtpnfs xijdi jt opu foboujpnfs. Ju ejggfst jo uif dpogjhvsbujpo po pof ps npsf tufsfpdfousft, cvu opu po bmm pg uifn.)

37) Enamine with propyl iodide

Draw the product of the reaction of cyclohexanone with morpholine, followed by the reaction with propyl iodide.



(Enciphered hint 1: Fobnjoft bsf gpsnfe cz uif sfbdujpo pg tfdpoebsz bnjoft xjui lfupoft.)


(Enciphered hint 1: Fobnjof bmlzmbujpo jo uif bmgb-qptjujpo jt gpmmpxfe cz gbtu izespmztjt pg uif jnjojvn tbmu.)

38) Procaine

Draw the structure of 2-(diethylamino)ethyl 4-aminobenzoate.


(Enciphered hint 1: Ftufs pg 4-bnjopcfoapjd bdje.)

39) Triethylamine with hydrogen chloride

Draw the product of the reaction of triethylamine with hydrogen chloride.



(Enciphered hint 1: Bo bnnpojvn tbmu jt gpsnfe.)

40) 1-Tert-butyl-4-nitrobenzene with hydrogen

Draw the product of the reaction of 1-tert-butyl-4-nitrobenzene with hydrogen on a platinum catalyst.



(Enciphered hint 1: Uif ojusp hspvq jt sfevdfe.)

41) Order of basicity 1

Choose the most basic and the least basic structure from the given compounds.



The most basic compound.


(Enciphered hint 1: Uif cbtjdjuz efqfoet po uif fmfduspojd fggfdut pg uif tvctujuvfout.)

The least basic compound.


(Enciphered hint 1: Uif cbtjdjuz efqfoet po uif fmfduspojd fggfdut pg uif tvctujuvfout.)

42) Order of basicity 2

Choose the most basic and the least basic structure from the given compounds.



The most basic compound.


(Enciphered hint 1: Uif cbtjdjuz efqfoet po uif fmfduspojd fggfdut pg uif tvctujuvfout.)

The least basic compound.


(Enciphered hint 1: Uif cbtjdjuz efqfoet po uif fmfduspojd fggfdut pg uif tvctujuvfout.)

43) Diazonium salt with H3PO2

Draw the product of the reaction of 2,4,6-tribromobenzenediazonium sulfate with phosphinic acid.



(Enciphered hint 1: Ejbap hspvq jt sfevdfe.)

44) Cyclopentanone with ethylamine

What product is formed by the reaction of cyclopentanone with ethylamine? First draw the intermediate adduct.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq jo uif gjstu tufq mfbet up b qsjnbsz joufsnfejbuf (hfnjobm bnjop bmdpipm).)


(Enciphered hint 1: Uif xbufs fmjnjobujpo mfbet up bo jnjof.)

45) Acetophenone with diethylamine

Draw the product of the reaction of acetophenone with diethylamine. First draw the intermediate adduct.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up b qsjnbsz beevdu (hfnjobm bnjop bmdpipm).)


(Enciphered hint 1: Fmjnjobujpo pg xbufs mfbet up bo fobnjof.)

46) Cyclohexanone with pyrrolidine

Draw the product of the reaction of cyclohexanone with pyrrolidine. First draw the intermediate adduct.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up bo beevdu (hfnjobm bnjop bmdpipm).)


(Enciphered hint 1: Xbufs fmjnjobujpo hjwft bo fobnjof.)

47) Reductive amination

The reaction of butanal with aniline in the presence of sodium cyanoborohydride leads first to an imine, which is subsequently reduced. First draw the structure of the imine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up bo jnjof.)

Next, draw the structure of the final product obtained by the reduction of the imine with sodium cyanoborohydride.


(Enciphered hint 1: Sfevdujpo pg uif D=O epvcmf cpoe ublft qmbdf.)

48) Cyclopentanone with hydroxylamine

What product is formed by the reaction of cyclopentanone with hydroxylamine? First draw the primary adduct.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet jo uif gjstu tufq up b hfnjobm bnjop bmdpipm.)


(Enciphered hint 1: Xbufs fmjnjobujpo mfbet up bo pyjnf.)

49) Acetophenone with hydrazine

Draw the product of the reaction of acetophenone with hydrazine and the product of its subsequent heating with potassium hydroxide.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf.)


(Enciphered hint 1: Xpmgg-Ljtiofs sfevdujpo.)

50) LDA

Draw the structure of lithium diisopropylamide.


(Enciphered hint 1: Tbmu efsjwfe gspn ejjtpqspqzmbnjof.)

51) Methadone

Draw the structure of 6-(dimethylamino)-4,4-diphenylheptan-3-one.


(Enciphered hint 1: Difdl uif qptjujpo pg gvodujpobm hspvqt.)

52) Ephedrine

Draw the structure of (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol.


(Enciphered hint 1: Vtf gvmm xfehf cpoe boe ebtife mjof up dpoofdu ofbsfs boe gvsuifs bupnt.)

53) Pseudoephedrine

Draw the structure of (1R,2R)-2-(methylamino)-1-phenylpropan-1-ol.


(Enciphered hint 1: Vtf gvmm xfehf cpoe boe ebtife mjof up dpoofdu ofbsfs boe gvsuifs bupnt.)

54) Amphetamine

Draw the structure of 1-phenylpropan-2-amine.


(Enciphered hint 1: B qsjnbsz bnjof.)

55) N-Methylaniline with ethyllithium

Draw all of the products of the reaction of N-methylaniline with ethyllithium.



(Enciphered hint 1: B tbmu boe bo bmlbof bsf gpsnfe.)

56) 4-Methylpent-3-en-2-one with nucleophile

Draw the product of the reaction of 4-methylpent-3-en-2-on with butylamine.



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

57) Benzaldehyde with methylamine

Draw the product of the reaction of benzaldehyde with methylamine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf gpsnjoh bo jnjof.)

58) Enamine with methyl iodide

Draw the product of the reaction of cyclopentanone with diethylamine, followed by the reaction with methyl iodide.



(Enciphered hint 1: Fobnjoft bsf gpsnfe cz uif sfbdujpo pg tfdpoebsz bnjoft xjui lfupoft.)


(Enciphered hint 1: Fobnjof bmlzmbujpo jo uif bmgb-qptjujpo jt gpmmpxfe cz gbtu izespmztjt pg uif jnjojvn tbmu.)

59) Structure to name (16)

Name the following structure:



(Enciphered hint 1: Ju jt bo bnjof.)

60) Synthesis of 1-chloro-4-iodobenzene

Draw the starting compound for the synthesis of 1-chloro-4-iodobenzene.



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

61) Pentan-3-one with dimethylamine

Draw the product of the reaction of pentan-3-one with dimethylamine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf.)

62) Reductive amination 3

Draw the product of the reaction of benzaldehyde with dibutylamine in the presence of sodium cyanoborohydride.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up bo jnjojvn tbmu, xijdi jt uifo sfevdfe cz uif bdujpo pg tpejvn dzbopcpspizesjef.)

63) Gabriel synthesis

The Gabriel synthesis is used for preparation of primary amines using potassium phthalimide. First draw the organic product of phthalimide alkylation and then the products after basic hydrolysis.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)


(Enciphered hint 1: Bo bnjof boe b tbmu pg ejdbscpyzmjd bdje bsf gpsnfe.)

64) Pyrrolidine with allyl bromide

Draw the product of the reaction of pyrrolidine with excess allyl bromide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. B rvbufsobsz bnnpojvn tbmu jt gpsnfe.)

65) Absolute configuration 7

Draw the three-dimensional structural formula of (R)-2-methylpiperidine.


(Enciphered hint 1: Tufsfpeftdsjqups S tqfdjgjft uif dpogjhvsbujpo po b tufsfphfojd dfousf (ifsf b dbscpo bupn cfbsjoh gpvs ejggfsfou tvctujuvfout).)

66) Enamine with ethyl acrylate

Draw the product of the reaction of the enamine with ethyl acrylate after water hydrolysis.