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1) 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.)

2) Acetone with dimethylamine

Draw the product of the reaction of acetone with dimethylamine.



(Enciphered hint 1: Bo fobnjof jt gpsnfe.)

3) 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.)

4) Hemiacetal formation from benzaldehyde

Fill in the intermediates of the hemiacetal formation from benzaldehyde.




(Enciphered hint 1: Bu gjstu qspupobujpo pg dbscpozm hspvq ublft qmbdf.)


(Enciphered hint 1: Ovdmfpqijmjd buubdl cz nfuibopm.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

5) Wittig reaction 2

Draw the product of the reaction of benzaldehyde with cyclopentylidenetriphenylphosphorane.



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

6) 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.)

7) 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.)

8) 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.)

9) 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.)

10) 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.)

11) 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.)

12) 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.)

13) 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.)

14) 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.)

15) Butanal with sodium cyanide

Draw the product of the reaction of butanal with sodium cyanide in the presence of an inorganic acid.



(Enciphered hint 1: Ovdmfpqijmjd beejujpo pg b dzbojef bojpo up b dbscpozm hspvq.)

16) Methyl phenyl ketone with NaBH4

Draw the product of the reaction of methyl phenyl ketone with sodium borohydride followed by the reaction with water.



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

17) 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.)

18) Phenylmagnesium bromide with butanal

Draw the product of the reaction of phenylmagnesium bromide with butanal 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.)

19) Hex-2-enal with nucleophile

Draw the product of the reaction of hex-2-enal with ethylmagnesium bromide, followed by addition of water.



(Enciphered hint 1: 1,2-Beejujpo pg uif ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf.)

20) Ethyl cyclopentanecarboxylate with EtMgBr

Draw the product of the reaction of ethyl cyclopentanecarboxylate with ethylmagnesium bromide.



(Enciphered hint 1: Uxp npmft pg uif pshbopnfubmmjd sfbhfou sfbdu xjui pof npmf pg ftufs. Uif gjstu frvjwbmfou pg uif sfbhfou gpsnt b lfupof, xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou.)

21) Propanal with HCN

Draw the product of the reaction of propanal with HCN, Then, the formed compound is treated under acidic hydrolysis conditions.



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


(Enciphered hint 1: Ojusjmf izespmztjt.)

22) Pentan-3-one and Beckmann rearangement

Pentan-3-one reacts with hydroxylamine and the formed compound is treated under acid-catalyzed conditions. Draw the products of both reactions.



(Enciphered hint 1: Izespyzmbnjof beejujpo up dbscpozm hspvq.)



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

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

Draw the product of the reaction of but-3-en-2-on with ethyllithium.



(Enciphered hint 1: 1,2-beejujpo qsfepnjobuft.)

24) Hex-2-enal with nucleophile

Draw the product of the reaction of hex-2-enal with methyllithium.



(Enciphered hint 1: 1,2-beejujpo ublft qmbdf.)

25) Diketene with water

Draw the product of the reaction of diketene with water.



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

26) 2-Methylpropanal with NH4Cl and NaCN

Draw the product of the reaction of 2-methylpropanal with ammonium chloride and sodium cyanide. The formed compound is then treated under acidic conditions.



(Enciphered hint 1: Bo bmgb-bnjopojusjmf jt gpsnfe jo uif sfbdujpo.)


(Enciphered hint 1: Ojusjmf izespmztjt ublft qmbdf.)

27) Butanal with hydroxylamine

Draw the product of the reaction of butanal with hydroxylamine.



(Enciphered hint 1: Ovdmfpqijmjd beejujpo pg izespyzmbnjof.)

28) Butanal with methanol

Draw the product of the acid-catalyzed reaction of butanal with two equivalents of methanol.



(Enciphered hint 1: Bdfubm gpsnbujpo.)

29) 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.)

30) Methyl phenyl ketone with propane-1,2-diol

Draw the product of the following reaction. Show the configuration of the product.



(Enciphered hint 1: Ovdmfpqijmjd beejujpo. Uif sfbdujpo epft opu qspdffe po uif tufsfphfojd dfousf boe uifsfgpsf op dibohf jo dpogjhvsbujpo pddvst.)

31) Wittig reaction 4

Draw the product of the reaction of cyclohexanone with methylidenetriphenylphosphorane.



(Enciphered hint 1: Xjuujh sfbdujpo hjwft bo bmlfof.)

32) Methyl phenyl ketone with sodium acetylide

Draw the product of the reaction of methyl phenyl ketone with sodium acetylide followed by the reaction with diluted sulfuric acid.



(Enciphered hint 1: Uif gjstu tufq jt beejujpo pg bdfuzmjef bojpo up uif dbscpozmf hspvq. Uif tfdpoe tufq jt bdjepcbtjd sfbdujpo pg uif bmdpipmbuf xjui ejmvufe tvmgvsjd bdje.)

33) Acyl chloride with methyllithium

Draw the product of the following reaction.



(Enciphered hint 1: Uxp npmft pg uif pshbopnfubmmjd sfbhfou sfbdu xjui pof npmf pg bdzm dimpsjef. Uif gjstu frvjwbmfou pg uif sfbhfou gpsnt b lfupof, xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou.)

34) 4-Methylpent-3-en-2-one with nucleophile

Draw the product of the reaction of 4-methylpent-3-en-2-one with methylmagnesium bromide.



(Enciphered hint 1: 1,2-Beejujpo pg uif ovdmfpqijmf ublft qmbdf.)

35) Phenylisocyanate with ethanol

Draw the product of the reaction of phenylisocyanate with ethanol.



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

36) Hex-2-enal with nucleophile

Draw the product of the reaction of hex-2-enal with sodium phenolate, followed by addition of water.



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

37) Benzaldehyde with HCN

Draw the product of the reaction of benzaldehyde with HCN, Then, the formed compound is treated under acidic hydrolysis conditions.



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


(Enciphered hint 1: Ojusjmf izespmztjt.)

38) Diketene with butan-1-ol

Draw the product of the reaction of diketene with butan-1-ol.



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

39) 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.)

40) Acetaldehyde with sodium methylacetylide

Acetaldehyde reacts with sodium methylacetylide to form a salt. Draw the structure of the salt. Then draw structure of subsequent reaction with diluted sulfuric acid.



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


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

41) 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.)

42) 1-Phenylprop-2-en-1-on with butyllithium

Does the reaction of 1-phenylprop-2-en-1-on with butyllithium proceed as 1,2- or 1,4-addition? Draw the product of the reaction after aqueous work-up.



(Enciphered hint 1: Qspevdu pg 1,2-beejujpo qsfepnjobuft.)

43) Pentano-5-lactone with methyllithium

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



(Enciphered hint 1: Ftufst xjui bmlzmmjuijvn sfbdu xjui 1:2 tupjdijpnfusz.)

44) Diphenyl ketone with sodium acetylide

Diphenyl ketone reacts with sodium acetylide to form a salt. Draw the structure of the salt. Then draw structure of subsequent reaction with diluted sulfuric acid.



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


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

45) Acetaldehyde in Strecker synthesis

Draw the product of the reaction of acetaldehyde with ammonium chloride and sodium cyanide. The formed compound is then treated under acidic conditions.



(Enciphered hint 1: Bo bmgb-bnjop ojusjmf jt gpsnfe jo uif sfbdujpo.)


(Enciphered hint 1: Ojusjmf izespmztjt ublft qmbdf.)

46) Butanal with ethylene glycol

Draw the product of the acid-catalyzed reaction of butanal with ethylene glycol.



(Enciphered hint 1: Bdfubm gpsnbujpo.)

47) Acetal formation from benzaldehyde hemiacetal (mechanism)

Fill in the intermediates of the acetal formation from the benzaldehyde hemiacetal.




(Enciphered hint 1: Bdujwbujpo pg izespyzm hspvq cz qspupobujpo pddvst.)


(Enciphered hint 1: TO1 sfbdujpo tubsut cz xbufs fmjnjobujpo.)


(Enciphered hint 1: Gjobm qspevdu jt gpsnfe.)

48) Wittig reaction 3

Describe the course of the reaction of methyl phenyl ketone with methylidenetriphenylphosphorane. First, draw the cyclic oxaphosphetane.



(Enciphered hint 1: B gpvs-nfncfs dzdmf (pybqiptqifubof) jt gpsnfe.)


(Enciphered hint 1: Esbx cpui qspevdut pg uif sfbdujpo.)

49) Wittig reaction 1

Draw the formula of methylenetriphenylphosphorane.


(Enciphered hint 1: Xjuujh sfbhfou.)

50) 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.)

51) L-Arabinose with HCN

Draw the three-dimensional structure of the product(s) of the following reaction.



(Enciphered hint 1: Beejujpo up uif dbscpozm hspvq zjfmet b njyuvsf pg ejbtufsfpjtpnfst pg dzbopizesjot.)

52) Acetone with sodium cyclohexylacetylide

Acetone reacts with sodium cyclohexylacetylide to form a salt. Draw the structure of the salt. Then draw structure of subsequent reaction with diluted sulfuric acid.



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


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

53) Benzaldehyde with sodium phenylacetylide

Draw the product of the reaction of benzaldehyde with sodium phenylacetylide followed by the reaction with diluted sulfuric acid.



(Enciphered hint 1: Uif gjstu tufq jt beejujpo pg bdfuzmjef bojpo up uif dbscpozmf hspvq. Uif tfdpoe tufq jt bo bdje-cbtf sfbdujpo pg uif bmdpipmbuf xjui ejmvufe tvmgvsjd bdje.)

54) Hex-2-enal with nucleophile

Draw the product of the reaction of hex-2-enal with potassium cyanide.



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

55) Phenylisocyanate with ethylamine

Draw the product of the reaction of phenylisocyanate with ethylamine.



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

56) Diketene with propylamine

Draw the product of the reaction of diketene with propylamine.



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

57) Cyclopentanone with sodium phenylacetylide

Draw the product of the reaction of cyclopentanone with sodium phenylacetylide followed by the reaction with diluted sulfuric acid.



(Enciphered hint 1: Uif gjstu tufq jt beejujpo pg bdfuzmjef bojpo up uif dbscpozmf hspvq. Uif tfdpoe tufq jt bo bdje-cbtf sfbdujpo pg uif bmdpipmbuf xjui ejmvufe tvmgvsjd bdje.)

58) Cyclohexanone and Beckmann rearangement

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



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



(Enciphered hint 1: Cfdlnboo sfbssbohfnfou. Dzdmjd bnjef (mbdubn) jt gpsnfe.)

59) Propyne reacts with organometallic and then with acetone

Propyne reacts with butylmagnesium bromide to form a salt. Then draw the structure of the product of a subsequent reaction with acetone, after work-up with diluted sulfuric acid.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)


(Enciphered hint 1: Uif gjstu tufq jt beejujpo pg bdfuzmjef bojpo up uif dbscpozmf hspvq. Uif tfdpoe tufq jt bo bdje-cbtf sfbdujpo pg uif bmdpipmbuf xjui ejmvufe tvmgvsjd bdje.)

60) Butylmagnesium bromide with ethanal

Draw the product of the reaction of butylmagnesium bromide with ethanal 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.)

61) Phenylmagnesium bromide with 1-phenylpropan-2-one

Draw the product of the reaction of phenylmagnesium bromide with 1-phenylpropan-2-one 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.)

62) Ethyl propanoate with CH3MgBr

Draw the product of the reaction of ethyl propanoate with two molar equivalents of methylmagnesium bromide (after acidification).



(Enciphered hint 1: Uxp npmft pg Hsjhobse sfbhfou sfbdu xjui pof npmf pg ftufs. Uif gjstu frvjwbmfou pg uif sfbhfou gpsnt b lfupof, xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou. Uif mbtu tufq - sfbdujpo pg uif bmlpyjef xjui xbufs - jt bo bdje-cbtf sfbdujpo.)

63) Preparation of pentan-1-ol from organometallic compound

Draw the requiered carbonyl compound of the following reaction:



(Enciphered hint 1: Dpnqbsf ovncfs pg dbscpo bupnt jo uif tubsujoh nbufsjbm boe jo uif qspevdu.)

64) 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.)

65) 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.)

66) Benzonitrile with butylmagnesium bromide

First draw the product of the reaction between benzonitrile and butylmagnesium bromide in diethyl ether and then the product after acidic hydrolysis.



(Enciphered hint 1: Uif tupjdijpnfusz pg uif sfbdujpo jt 1:1.)


(Enciphered hint 1: Izespmztjt bggpset b dbscpozm dpnqpvoe.)

67) Acetonitrile with butylmagnesium chloride

First draw the product of the reaction between acetonitrile and butylmagnesium chloride in diethyl ether and then the product after acidic hydrolysis.



(Enciphered hint 1: Uif tupjdijpnfusz pg uif sfbdujpo jt 1:1.)