Print questions | Press CTRL-P to print

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) 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.)

3) Lactam with LiAlD4

Draw the product of the following reaction.



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

4) Strength of acids 4

Choose the most acidic and the least acidic compound.



The most acidic compound.


(Enciphered hint 1: Dpotjefs bdjejuz pg wbsjpvt dmbtt pg dpnqpvoet.)

The least acidic compound.


(Enciphered hint 1: Dpotjefs bdjejuz pg wbsjpvt dmbtt pg dpnqpvoet.)

5) 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.)

6) Mechanism of ethyl acetate hydrolysis

Draw the structure of an intermediate in acid-catalyzed hydrolysis of ethyl acetate, which is formed by the reaction of protonated form of the ester with water.



(Enciphered hint 1: Beejujpo pg uif ovdmfpqijmf up uif qspupobufe dbscpyzmjd hspvq.)

7) Nomenclature IX

Draw the structure of 2-chloroacetyl chloride.


(Enciphered hint 1: Bdfuzm dimpsjef jt dimpsjef pg bdfujd bdje.)

8) 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.)

9) Nomenclature VIII

Draw the structure of 4-bromo-2,2-diphenylbutane nitrile.


(Enciphered hint 1: Tvctujuvufe ojusjmf pg cvubopjd bdje.)

10) Dieckmann condensation

Draw the products of the following reaction.



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

11) 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.)

12) Mixed claisen condensation 2

Draw the product of the mixed Claisen condensation of ethyl phenylacetate with diethyl oxalate.



(Enciphered hint 1: B cfub-lfup ftufs jt gpsnfe.)

13) Nomenclature I

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


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

14) 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.)

15) Nitrile with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo pg cpui gvodujpobm hspvqt ublft qmbdf.)

16) Amide with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

17) Pentano-5-lactone with LiAlD4

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



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

18) Pentano-5-lactone with DIBAH

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



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

19) Butanoyl chloride with ammonia

Draw all products of the reaction of butanoyl chloride with excess ammonia.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo. Ep opu gpshfu uif jopshbojd qspevdu.)

20) Butanoic anhydride with ethanol

Draw butanoic anhydride and the organic products of its reaction with ethanol catalysed by sulfuric acid.


(Enciphered hint 1: Cvubopjd bdje boizesjef.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

21) Butyronitrile with lithium aluminium hydride

Draw the product of the reaction of butyronitrile with lithium aluminium hydride.



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

22) Acidic hydrolysis of nitriles

Draw the product for the reaction of 2-(4-nitrophenyl)acetonitrile with water in the presence of sulfuric acid.



(Enciphered hint 1: Izespmztjt pg uif ojusjmf hspvq ublft qmbdf.)

23) Nomenclature X

Draw the structure of diethyl 2-(ethoxymethylene)malonate.


(Enciphered hint 1: Nbmpobuf jt ftufs pg qspqbofejpjd bdje.)

24) Mechanism of acetamide hydrolysis

Draw the intermediate of the alkaline amide hydrolysis that is formed by the reaction of acetamide with hydroxide anion.



(Enciphered hint 1: Beejujpo pg uif ovdmfpqijmf up uif dbscpyzm hspvq.)

25) Mixed claisen condensation

Draw the products of Claisen condensation of ethyl benzoate with ethyl acetate.



(Enciphered hint 1: Cfub-lfup ftufs jt gpsnfe.)

26) Dibromoderivative with sodium cyanide

Draw the product of the following reaction.



(Enciphered hint 1: Bszm ibmjeft bsf vosfbdujwf jo ovdmfpqijmjd tvctujuvujpot.)

27) Alkylation of enolate

Draw the product of the following reaction.



(Enciphered hint 1: Bmlzmbujpo pg bo fopmbuf ublft qmbdf.)

28) Phthalic anhydride with butan-1-amine

Draw phthalic anhydride and the product of its reaction with butan-1-amine.


(Enciphered hint 1: Qiuibmjd bdje boizesjef (boizesjef pg cfoafof-1,2-ejdbscpyzmjd bdje).)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

29) Propanoyl chloride with aniline

Draw the product of the reaction of propanoyl chloride with aniline in the presence of triethylamine.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

30) 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.)

31) Structure to name (23)

Name the following structure:



(Enciphered hint 1: Ju jt bo pyp ftufs.)

32) 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.)

33) 1-Iodopentane with sodium acetate

Draw the product of the following reaction.


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

34) Ethyl propanoate with LiAlH4

Draw the organic products of the following reaction.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

35) Hoffmann rearrangement

Draw all the carbon-containing products of the Hoffmann rearrangement of phenylacetamide.



(Enciphered hint 1: Bo bnjef jt dpowfsufe joup b qsjnbsz bnjof.)

36) Alkaline hydrolysis of nitriles

Draw the product of the reaction of pentanenitrile with water in the presence of hydroxide ions.



(Enciphered hint 1: Izespmztjt pg uif ojusjmf hspvq pddvst jo bmlbmjof nfejvn.)

37) Butano-4-lactone with ammonia

Draw butano-4-lactone and the product of its reaction with ammonia.


(Enciphered hint 1: B dzdmjd ftufs.)


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo po uif dbscpyzm hspvq.)

38) Furan with maleic anhydride

Draw the product of the following reaction.



(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

39) Bromisoval

Draw the structure of 2-bromo-N-carbamoyl-3-methylbutanamide.


(Enciphered hint 1: Dbscbnpzm nfbot -DPOI2 hspvq.)

40) Claisen condensation of ethyl phenylacetate

Draw the product of the Claisen condensation of ethyl phenylacetate.



(Enciphered hint 1: Cfub-lfup ftufs jt gpsnfe.)

41) 1-Iodopentane with sodium cyanide

Draw the product of the reaction of 1-iodopentane with sodium cyanide.


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

42) Alkylation of enolate 2

Draw the product of the following reaction.



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

43) N-bromosuccinimide

Draw the structure of N-bromosuccinimide which is used for radical brominations.


(Enciphered hint 1: Ju jt b efsjwbujwf pg dzdmjd jousbnpmfdvmbs bnjef pg tvddjojd (cvubofejpjd) bdje.)

44) 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.)

45) Lactam with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

46) Malonic ester synthesis

The malonic ester synthesis is used for preparation of carboxylic acids. The starting compounds are diethyl malonate and alkyl halide. Draw the structure of alkyl bromide, which is used for the synthesis of 4-methylhexanoic acid.



(Enciphered hint 1: Ejfuizm nbmpobuf jt b tpvsdf pg uif tzouipo -DI2DPPI.)

47) Ethyl 2-phenylacetate with DIBAH

Draw the product of the following reaction of ethyl 2-phenylacetate.



(Enciphered hint 1: Difnptfmfdujwf sfevdujpo ublft qmbdf.)

48) Diester with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Cpui ftufs gvodujpobm hspvqt sfbdu.)

49) 3-Methylcyclohexanol with acyl chloride

Draw the product of the following reaction. Use wedged bonds to indicate the position of the substituents.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

50) Maleic anhydride with ammonia

Draw maleic anhydride and the product of its reaction with excess ammonia.


(Enciphered hint 1: Nbmfjd bdje boizesjef.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

51) Curtius rearrangement

Draw all the products (including inorganic) of the Curtius rearrangement of benzoyl azide.



(Enciphered hint 1: Qsjnbsz bnjoft bsf gpsnfe cz Dvsujvt sfbssbohfnfou pg bdzm bajeft.)

52) Reactions of amides

What product is formed by the reaction of pyridine-3-carboxamide with phosphorus(V) oxide?



(Enciphered hint 1: Efizesbujpo ublft qmbdf.)

53) Succinic anhydride with ethanol

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



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo. Ftufsjgjdbujpo pddvst bgufs sjoh pqfoojoh.)

54) 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.)

55) Claisen condensation of ethyl-propanoate

Draw the product of the Claisen condensation of ethyl propanoate.



(Enciphered hint 1: Cfub-lfup ftufs jt gpsnfe.)

56) 1-Bromo-3-chloropropane with sodium cyanide

Draw 1-bromo-3-chloropropane and the product of its reaction with one molar equivalent of sodium cyanide.


(Enciphered hint 1: Qspqbof xjui cspnjof boe dimpsjof jo uif qptjujpot 1 boe 3.)


(Enciphered hint 1: Cspnjef bojpo jt cfuufs mfbwjoh hspvq uibo dimpsjef bojpo.)

57) Dibromoderivative with sodium cyanide 2

Draw the major product of the following reaction.



(Enciphered hint 1: Dpnqbsf uif sfbdujwjuz pg b qsjnbsz bmlzm ibmjef boe b wjozmjd ibmjef.)

58) Acetyl chloride with phenol

Draw all products of the reaction between acetyl chloride and phenol in the presence of triethylamine.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo. Ep opu gpshfu uibu usjfuizmbnjof jt qsftfou.)

59) Benzoyl chloride with diethylamine

Draw benzoyl chloride and all products of its reaction with excess diethylamine.


(Enciphered hint 1: Cfoapjd bdje dimpsjef.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

60) Strength of acids 1

Choose the most acidic and the least acidic compound.



The most acidic compound.


(Enciphered hint 1: Dpotjefs fmfduspojd fggfdu pg tvctujuvfout.)

The least acidic compound.


(Enciphered hint 1: Dpotjefs fmfduspojd fggfdu pg tvctujuvfout.)

61) Reactivity in nucleophilic acyl substitution

All of the following acetic acid derivatives react with ammonia upon formation of acetamide. Choose the most reactive one.



(Enciphered hint 1: Uif sfbdujwjuz jt jodsfbtfe cz uif qsftfodf pg bo fmfduspo-xjuiesbxjoh hspvq jo uif npmfdvmf.)

62) 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.)

63) Benzoyl chloride with sodium acetate

Draw the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

64) Mechanism of benzoyl chloride hydrolysis

Draw the structure of the intermediate of benzoyl chloride hydrolysis.



(Enciphered hint 1: Beejujpo pg uif ovdmfpqijmf up uif dbscpyzmjd hspvq.)

65) Cleavage of an acetate

Draw the major product of the thermal cleavage of the following acetate.



(Enciphered hint 1: Bdfubuf dmfbwbhf. Ju jt tzo- cfub-fmjnjobujpo pg bdfujd bdje.)

66) Claisen condensation of ethyl acetate

Draw the products of the following reactions.



(Enciphered hint 1: Bo fopmbuf pg cfub-lfupftufs jt gpsnfe.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo. B cfub-lfupftufs jt gpsnfe.)

67) Ethyl acetoacetate 2

Draw ethyl acetoacetate and the product of its reaction with two equivalents of LDA.


(Enciphered hint 1: Fuizm 3-pypcvubopbuf.)


(Enciphered hint 1: Epvcmf efqspupobujpo.)

68) Procaine

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


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