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1) 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.)

2) 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.)

3) 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.)

4) 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.)

5) 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.)

6) 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.)

7) 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.)

8) Ethyl chloroformate with methylamine

Draw the product of the reaction of ethyl chloroformate with methylamine.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo pg dimpsjef ublft qmbdf.)

9) 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.)

10) 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.)

11) 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.)

12) 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.)

13) 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.)

14) 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.)

15) Propanoic acid with SOCl2

Draw the product of the reaction of propanoic acid with thionyl chloride.



(Enciphered hint 1: Qsfqbsbujpo pg bdzm dimpsjef.)

16) Esterification - mechanism

An important intermediate is formed in the reaction of activated (protonated) carboxylic acid with alcohol during Fischer exterification. Draw its structure.



(Enciphered hint 1: B ufusbfesjd joufsnfejbuf jt gpsnfe.)

17) Heating of 2-amino-2-phenylacetic acid

Draw the product of the reaction of 2-amino-2-phenylacetic acid when heated.



(Enciphered hint 1: Xifo ifbufe, bmgb-bnjop bdjet ejnfsjaf gpsnjoh uxp bnjef cpoet.)

18) Boc-protecting group and phenylalanine

The Boc protecting group (Boc = tert-butoxycarbonyl) is often used to protect aminogroups. Draw the structure of di-tert-butyl dicarbonate - (Boc)2O, the reagent used for introduction of the protecting group and then draw the product of its reaction with phenylalanine.


(Enciphered hint 1: Dbscpojd bdje boizesjef efsjwbujwf.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo ublft qmbdf.)

19) Boc-protecting group and leucine

The Boc protecting group (Boc = tert-butoxycarbonyl) is often used to protect aminogroups. Draw the structure of di-tert-butyl dicarbonate - (Boc)2O, the reagent used for introduction of the protecting group and then draw the product of its reaction with leucine.


(Enciphered hint 1: Dbscpojd bdje boizesjef efsjwbujwf.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo ublft qmbdf.)

20) Z-protecting group and valine

The Z group (also known as Cbz, benzyloxycarbonyl) is often used to protect amino groups. Draw the structure of benzyl chloroformate (Z-Cl), the reagent used for introduction of the protecting group and then draw the product of its reaction with valine.


(Enciphered hint 1: Njyfe cfoazm ftufs dimpsjef pg dbscpojd bdje.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo ublft qmbdf.)

21) D-Allopyranose with acetic anhydride

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



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

22) 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.)

23) Ethyl propanoate with LiAlH4

Draw the organic products of the following reaction.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

24) 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.)

25) L-Proline with EtOH/HCl

Draw the product of the reaction of L-proline with HCl in ethanol.



(Enciphered hint 1: Ftufsjgjdbujpo pg dbscpyzmjd bdje ublft qmbdf.)
(Enciphered hint 2: Bo bnjop hspvq xjui IDm gpsnt jut tbmu.)

26) Heating of 4-aminohexanoic acid

Draw the product of the reaction of 4-aminohexanoic acid when heated.



(Enciphered hint 1: Bo jousbnpmfdvmbs sfbdujpo ublft qmbdf. B dzdmjd bnjef jt gpsnfe.)

27) Propanoic acid with PBr3

Draw the product of the reaction of propanoic acid with phosphorus tribromide.



(Enciphered hint 1: Qsfqbsbujpo pg bdzm cspnjef.)

28) 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.)

29) (E)-2-Methylbut-2-enoic acid with ethanol

Draw the product of the reaction of (E)-2-methylbut-2-enoic acid with ethanol in the presence of sulfuric acid.



(Enciphered hint 1: Gjtdifs ftufsjgjdbujpo.)

30) 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.)

31) Glycine with EtOH/HCl

Draw the product of the reaction of glycine with HCl in ethanol.



(Enciphered hint 1: Ftufsjgjdbujpo pg dbscpyzmjd bdje ublft qmbdf.)
(Enciphered hint 2: Bo bnjop hspvq xjui IDm gpsnt jut tbmu.)

32) 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.)

33) Heating of 5-aminohexanoic acid

Draw the product of the reaction of 5-aminohexanoic acid when heated.



(Enciphered hint 1: Bo jousbnpmfdvmbs sfbdujpo ublft qmbdf. B dzdmjd bnjef jt gpsnfe.)

34) D-Talopyranose with acetic anhydride

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



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

35) Z-Val with Leu-OCH2Ph

Draw the products of the following reactions.



(Enciphered hint 1: B qfqujef cpoe jt gpsnfe.)


(Enciphered hint 1: Izesphfopmztjt sfnpwft cpui qspufdujoh hspvqt.)

36) 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.)

37) 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.)

38) 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.)

39) Benzoyl chloride with sodium acetate

Draw the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

40) 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.)

41) Boc-Leu with Pro-OCH3

Draw the products of the following reactions.



(Enciphered hint 1: B qfqujef cpoe jt gpsnfe. Uif bnjop hspvq pg mfvdjof jt qspufdufe cz ufsu-cvupyzdbscpozm hspvq. Uif dbscpyzmjd gvodujpobm hspvq pg qspmjof jt qspufdufe bt nfuizm ftufs.)


(Enciphered hint 1: Uif ufsu-cvupyzdbscpozm hspvq jt dmfbwfe.)


(Enciphered hint 1: Uif ftufs izespmztjt ublft qmbdf.)

42) Cyclohexanecarbonyl chloride with sodium benzoate

Draw the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

43) Heating of 2-aminohexanoic acid

Draw the product of the reaction of 2-aminohexanoic acid when heated.



(Enciphered hint 1: Xifo ifbufe, bmgb-bnjop bdjet ejnfsjaf gpsnjoh uxp bnjef cpoet.)

44) Ethyl benzoate with phenyllithium

Draw the product of the reaction of ethyl benzoate with phenyllithium.



(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.)

45) Z-protecting group and phenylalanine

The Z-group (also known as Cbz, benzyloxycarbonyl) is often used to protect amino groups. Draw the structure of benzyl chloroformate (Z-Cl), the reagent used for introduction of the protecting group and then draw the product of its reaction with phenylalanine.


(Enciphered hint 1: Njyfe cfoazm ftufs dimpsjef pg dbscpojd bdje.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo ublft qmbdf.)

46) Acetyl chloride with Et2CuLi

Draw the product of the reaction of acetyl chloride with lithium diethylcuprate.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo. Uif qspevdu jt b lfupof.)

47) 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.)

48) Boc-Pro with Leu-OEt

Draw the products of the following reactions.



(Enciphered hint 1: B qfqujef cpoe jt gpsnfe. Uif bnjop hspvq pg qspmjof jt qspufdufe cz ufsu-cvupyzdbscpozm hspvq. Uif dbscpyzmjd gvodujpobm hspvq pg mfvdjof jt qspufdufe bt fuizm ftufs.)


(Enciphered hint 1: Uif ufsu-cvupyzdbscpozm hspvq jt dmfbwfe.)


(Enciphered hint 1: Ftufs izespmztjt ublft qmbdf.)

49) Diethyl malonate with methylamine

Draw all products of the reaction of diethyl malonate with methylamine.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo.)

50) Isoamyl alcohol with acetic acid

Draw isoamyl alcohol and the product of its reaction with acetic acid in the presence of sulfuric acid.


(Enciphered hint 1: Jtpbnzm nfbot 3-nfuizmcvuzm hspvq.)


(Enciphered hint 1: Gjtdifs ftufsjgjdbujpo ublft qmbdf. )