Print questions | Press CTRL-P to print

1) 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.)

2) 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.)

3) Acetone with dimethylamine

Draw the product of the reaction of acetone with dimethylamine.



(Enciphered hint 1: Bo fobnjof jt gpsnfe.)

4) 3-Methylcyclohex-2-en-1-one with phenylmethanethiol

Draw the product of the following reaction.



(Enciphered hint 1: Dpokvhbufe beejujpo.)

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) 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.)

7) Wittig reaction 2

Draw the product of the reaction of benzaldehyde with cyclopentylidenetriphenylphosphorane.



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

8) Keto and enol forms 3

Draw the keto and enol forms of 2,4-pentanedione.


(Enciphered hint 1: Ubvupnfst.)

9) 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.)

10) 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.)

11) 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.)

12) 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.)

13) 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.)

14) 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.)


15) 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.)

16) 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.)

17) 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.)

18) Cyclohexanone with LDA

Draw the product (anion only) of the reaction of cyclohexanone with lithium diisopropylamide.



(Enciphered hint 1: Bdje-cbtf sfbdujpo. Bo fopmbuf jt gpsnfe.)

19) Butanal with hydrogen

Draw the product of the reaction of butanal with hydrogen catalyzed by nickel.



(Enciphered hint 1: Dbubmzujd izesphfobujpo.)

20) 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.)

21) 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.)

22) 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.)

23) Cyclohexanone with chlorine

Draw the product of the reaction of cyclohexanone with chlorine in an aqueous medium.



(Enciphered hint 1: Tvctujuvujpo po uif bmqib dbscpo ublft qmbdf.)

24) Phosphonium salt 3

Draw the product of the reaction of methyl triphenyl phosphonium bromide with dimsyl sodium (sodium salt of dimethylsulfoxide).



(Enciphered hint 1: Bdje-cbtf sfbdujpo. Bo zmjef jt gpsnfe.)

25) Enolates 1

Describe the mechanism of the reaction of acetone with hydroxide ion in an aqueous medium and the formation of enolate.



(Enciphered hint 1: Bdje-cbtf frvjmmjcsjvn.)


(Enciphered hint 1: Sftpobodf tusvduvsf.)

26) Haloform reaction 2

Draw all the products of the reaction of tert-butyl methyl ketone with bromine in the presence of sodium hydroxide.



(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.)

27) Aldol condensation

Draw the final product which is formed when heating acetophenone (methyl phenyl ketone) in the presence of tert-butoxide ions in xylene at 100 °C.



(Enciphered hint 1: Bmepm dpoefotbujpo ublft qmbdf.)

28) 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.)

29) Aldolization of propanal

Draw the structures of the intermediates and the products of the aldol reaction of propanal.



(Enciphered hint 1: Fopmbuf jt gpsnfe.)


(Enciphered hint 1: Sfbdujpo pg fopmbuf xjui bmefizef.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

30) Nomenclature I

Draw the structure of N-(3-acetylphenyl)acetamide.


(Enciphered hint 1: Bdfuzm nfbot DI3D=P hspvq.)

31) Claisen condensation

From the following compounds choose the ones which will presumably give high yields in Claisen condensation.



(Enciphered hint 1: Uxp izesphfo bupnt bu uif bmgb-qptjujpo bsf ofddftbsz gps tnppui Dmbjtfo dpoefotbujpo.)

32) 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.)

33) Intramolecular aldol condensation 2

Draw the products of heating of 3-methylhexane-2,5-dione in the presence of sodium hydroxide.



(Enciphered hint 1: Jousbnpmfdvmbs bmepm dpoefotbujpo ublft qmbdf. Uif dzdmf dbo cf gpsnfe wjb uxp xbzt.)

34) Aldolization - synthesis 2

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



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

35) 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.)

36) 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.)

37) Benzaldehyde with KOH

Benzaldehyde reacts with KOH. Draw the organic products of the reaction after its acidic work-up.



(Enciphered hint 1: Dboojaabsp sfbdujpo ublft qmbdf xifo bmefizeft xjuipvu bmgb izesphfo bsf usfbufe voefs cbtjd dpoejujpot.)

38) 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.)

39) 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.)

40) Butanal with hydroxylamine

Draw the product of the reaction of butanal with hydroxylamine.



(Enciphered hint 1: Ovdmfpqijmjd beejujpo pg izespyzmbnjof.)

41) Butanal with methanol

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



(Enciphered hint 1: Bdfubm gpsnbujpo.)

42) Butanal with chromium(VI) oxide

Draw the product of the reaction of butanal with chromium(VI) oxide.



(Enciphered hint 1: Pyjebujpo pg uif dbscpozm hspvq.)

43) 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.)

44) Methyl phenyl ketone with zinc amalgam

Draw the product of the reaction of methyl phenyl ketone with zinc amalgam in the presence of hydrochloric acid.



(Enciphered hint 1: Sfevdujpo pg uif dbscpozm hspvq.)

45) 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.)

46) Wittig reaction 4

Draw the product of the reaction of cyclohexanone with methylidenetriphenylphosphorane.



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

47) Keto and enol form 1

Draw the keto and enol forms of acetone.


(Enciphered hint 1: Ubvupnfst.)

48) 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.)

49) Cyclohexanecarbaldehyde with bromine

Draw the product of the reaction of cyclohexanecarbaldehyde with bromine in chloroform.



(Enciphered hint 1: Tvctujuvujpo po uif bmqib dbscpo ublft qmbdf.)

50) Reaction of acetophenone with peroxyacetic acid

Draw the product of the oxidation of acetophenone with peroxyacetic acid.



(Enciphered hint 1: Cbfzfs-Wjmmjhfs sfbdujpo.)

51) Aldolization

Draw the structures of intermediates and products formed by aldolization of butanal.



(Enciphered hint 1: Uif sfbdujpo pg bmefizef xjui cbtf hjwft bo fopmbuf.)


(Enciphered hint 1: Uif fopmbuf pg uif gjstu bmefizef sfbdut xjui uif dbscpozm hspvq pg uif tfdpoe bmefizef.)


(Enciphered hint 1: Uif bmepm jt gpsnfe.)

52) Aldolization of aceton

Draw the product of the heating of acetone in the presence of barium hydroxide.



(Enciphered hint 1: Gpsnbujpo pg cfub-izespyzlfupof cz uif sfbdujpo pg fopmbuf xjui "ofvusbm" bdfupof.)

53) 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.)

54) Intramolecular aldol condensation

Draw the product of heating of hexane-2,5-dione in the presence of sodium hydroxide.



(Enciphered hint 1: Jousbnpmfdvmbs bmepm dpoefotbujpo ublft qmbdf.)

55) 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.)

56) 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.)

57) 2,2,2-Triphenylacetaldehyde with NaOH

2,2,2-Triphenylacetaldehyde reacts with NaOH. Draw the organic products of the reaction after its acidic work-up.



(Enciphered hint 1: Dboojaabsp sfbdujpo ublft qmbdf xifo bmefizeft xjuipvu bmgb izesphfo bsf usfbufe voefs cbtjd dpoejujpot.)

58) 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.)

59) 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.)

60) 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.)

61) 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.)

62) Halogenation of cyclopentanone

An enol form of cyclopentanone is formed in the first step of brominantion of cyclopentanone in acetic acid. Draw the formula of enol form and then the product of its bromination.

(Enciphered hint 1: Ubvupnfsjd gpsn pg dzdmpqfoubopof.)


(Enciphered hint 1: Fmfduspqijmjd gpsn pg dzdmpqfoubopof sfbdu xjui fmfduspqijmjd cspnjof.njof.)

63) 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.)

64) Synthesis of 3-phenylpropan-2-one from alkyne.

Draw the structure of alkyne giving by hydration the following ketone.



(Enciphered hint 1: Beejujpo pg xbufs gpmmpxfe cz jtpnfsjabujpo pg qsjnbsjmz gpsnfe beevdu.)
(Enciphered hint 2: Uif qptjujpo pg uif usjqmf cpoe qmbzt bo jnqpsubou spmf jo uif sfbdujpo: ufsnjobm bmlzoft pomz hjwf nfuizm lfupoft.)

65) Butanal with ethylene glycol

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



(Enciphered hint 1: Bdfubm gpsnbujpo.)

66) Hexanal with chromium(VI) oxide

Draw the product of the reaction of hexanal with chromium(VI) oxide.



(Enciphered hint 1: Pyjebujpo pg uif dbscpozm hspvq.)

67) 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.)

68) 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.)

69) Keto and enol form 2

Draw the keto and enol forms of cyclopentanone.


(Enciphered hint 1: Ubvupnfst.)

70) Acetone with magnesium

A radical anion is formed by the reaction of acetone with magnesium. Draw the structure of the radical anion.



(Enciphered hint 1: Tjohmf-fmfduspo sfevdujpo pg bdfupof.)

Draw the product of the coupling reaction between two radical anions followed by the reaction with water.


(Enciphered hint 1: Qjobdpm dpvqmjoh sfbdujpo.)

71) Enolates 2

Write the equation for the reaction of 2-methyl-1,3-cyclopentadione with hydroxide anion. First, draw the formation of a carbanion.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)


(Enciphered hint 1: Sftpobodf tusvduvsf.)

72) Reaction of cyclohexanone with peroxyacetic acid

Draw the product of the oxidation of cyclohexanone with peroxyacetic acid.



(Enciphered hint 1: Cbfzfs-Wjmmjhfs sfbdujpo.)

73) Aldol dehydration.

What product is formed by heating 2-ethyl-3-hydroxyhexanal?



(Enciphered hint 1: Xbufs fmjnjobujpo ublft qmbdf.)

74) 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.)

75) 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.)

76) Aldolization of phenylacetaldehyde

Draw the structures of the intermediates and the products of the aldol reaction of phenylacetaldehyde.



(Enciphered hint 1: Fopmbuf jt gpsnfe.)