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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) D-Xylose with bromine

Draw the three-dimensional structure of the open-chain form of the product of the following reaction.



(Enciphered hint 1: Pyjebujpo pg uif dbscpozm hspvq ublft qmbdf. Bmepojd bdje jt gpsnfe.)

3) p-Isopropyltoluene with sodium dichromate

Draw the product of the reaction of 1-isopropyl-4-methylbenzene with sodium dichromate.



(Enciphered hint 1: Pyjebujpo pddvst jo uif tjef dibjo pg uif bspnbujd sjoh.)

4) Ozonolysis of 2,4,4-trimethylpent-2-ene

Draw the product(s) of the following reaction.



(Enciphered hint 1: Uif gjstu tufq mfbet up bo papojef xijdi jt uifo izespmzafe voefs sfevdujwf dpoejujpot up uif gjobm qspevdut.)

5) Oxidation of thiols 2

Draw the product of the reaction of cyclopentanethiol with bromine.



(Enciphered hint 1: Uif uijpm jt pyjejafe up gpsn b ejtvmgjef.)

6) Oxidation of thiols 3

Draw the product of the reaction of thiophenol with nitric acid.



(Enciphered hint 1: Pyjebujpo pg uif uijpm pddvst bu tvmgvs bupn. Tvmgpojd bdje jt gpsnfe.)

7) Dithiol in the presence of oxygen

Draw the product of the following reaction.



(Enciphered hint 1: Uif uijpm jt pyjejafe up gpsn b ejtvmgjef.)

8) Oxidation of an unsaturated alcohol

Draw the product of the oxidation of but-3-en-1-ol with PCC (pyridinium chlorochromate).



(Enciphered hint 1: Difnptfmfdujwf pyjebujpo.)

9) D-Glucose with HNO3

Draw the three-dimensional structure of the product of the following reaction.



(Enciphered hint 1: Pyjebujpo pg uif dbscpo bupnt D1 boe D6 ublft qmbdf. Bmebsjd bdje jt gpsnfe.)

10) Synthesis of D-arabinaric acid

Which pentose gives the same aldaric acid as D-arabinose on oxidation with nitric acid? Draw the three-dimensional structure of its open-form.



(Enciphered hint 1: Ju jt bopuifs E-qfouptf.)
(Enciphered hint 2: E-Mzyptf.)

11) 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.)

12) Synthesis of benzoic acid

Draw the starting alcohol, which is oxidised to benzoic acid by the reaction with potassium dichromate in sulfuric acid.



(Enciphered hint 1: Qsjnbsz bmdpipm.)

13) Ozonolysis of unknown alkyne (3)

The given compounds are the products of ozonolysis of an alkadiyne. Draw its structure.



(Enciphered hint 1: Dbscpyzmjd gvodujpot bsf gpsnfe cz dmfbwbhf pg usjqmfu cpoet.)

14) (E)-Pent-2-ene with osmium tetroxide

Draw the product(s) of the following reaction. Draw the correct stereochemistry.



(Enciphered hint 1: Izespyzmbujpo pg b epvcmf cpoe. Sbdfnbuf jt gpsnfe.)

15) p-Xylene with potassium permanganate

Draw the product of the reaction of p-xylene with potassium permanganate.



(Enciphered hint 1: Pyjebujpo pddvst jo uif tjef dibjo pg uif bspnbujd sjoh.)

16) Starting alcohol 1

Which alcohol would you oxidize to get the product shown below?



(Enciphered hint 1: Uif tubsujoh dpnqpvoe jt b tfdpoebsz bmdpipm.)

17) PCC

Pyridinium chlorochromate (PCC) is a selective oxidation agent used for the oxidation of alcohols. Draw the structure of PCC.


(Enciphered hint 1: QDD jt b qzsjejojvn tbmu.)

18) Ozonolysis of 1,2,3,4,5,6,7,8-octahydronaphthalene

Draw the product of the ozonolysis of 1,2,3,4,5,6,7,8-octahydronaphthalene.



(Enciphered hint 1: Uif gjstu tufq mfbet up bo papojef xijdi jt uifo izespmzafe up uif gjobm qspevdu.)

19) Thiophene with peroxybenzoic acid

Draw the product of the reaction of thiophene with peroxybenzoic acid.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)

20) Oxidation of hexanol 2

What product will you get by the oxidation of hexan-1-ol using chromium(VI) oxide in aqueous acid?



(Enciphered hint 1: Gpvs-fmfduspo pyjebujpo ublft qmbdf. )

21) Oxidation of hexanol

What product will you get by the oxidation of hexan-1-ol using PCC?



(Enciphered hint 1: Uxp-fmfduspo pyjebujpo ublft qmbdf.)

22) 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.)

23) Synthesis of D-glucaric acid

Which hexose gives the same aldaric acid as D-glucose on oxidation with nitric acid? Draw the three-dimensional structure of its open-form.



(Enciphered hint 1: Jut bo M-ifyptf.)
(Enciphered hint 2: M-Hvmmptf.)

24) Ozonolysis of oct-4-yne

Write the products of ozonolysis of the alkyne shown in the picture.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg usjqmf cpoe voefs gpsnbujpo pg dbscpyzmjd hspvqt.)

25) Phenol oxidation

Draw the product of phenol oxidation with potassium dichromate.



(Enciphered hint 1: B ejdbscpozm dpnqpvoe jt gpsnfe.)

26) Reaction of acetophenone with peroxyacetic acid

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



(Enciphered hint 1: Cbfzfs-Wjmmjhfs sfbdujpo.)

27) 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.)

28) Toluene with potassium permanganate

Draw the product of the reaction of toluene with potassium permanganate.



(Enciphered hint 1: Pyjebujpo pddvst jo uif tjef dibjo pg uif bspnbujd sjoh.)

29) Pentan-1-ol with chromium(VI) oxide

Draw the organic product of the reaction of pentan-1-ol with chromium trioxide in aqueous sulfuric acid.



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

30) 2,3-Dimethylnaphthalene with Na2Cr2O7

Draw the product of the reaction of 2,3-dimethylnaphthalene with sodium dichromate.



(Enciphered hint 1: Pyjebujpo pg nfuizm hspvqt dpoofdufe up uif bspnbujd sjoh ublft qmbdf.)

31) But-1-ene with MCPBA

Draw all products of the following reaction.



(Enciphered hint 1: Fqpyjebujpo pg b epvcmf cpoe.)

32) (Z)-Pent-2-ene with osmium tetroxide

Draw the product(s) of the following reaction. Draw the correct stereochemistry.



(Enciphered hint 1: Izespyzmbujpo pg b epvcmf cpoe. Sbdfobuf jt gpsnfe.)

33) Oxidation of vicinal diol 2

Draw the product(s) of the reaction of 2,4-dimethylpentane-2,3-diol with periodic acid.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg uif bdujwbufe D-D cpoe ublft qmbdf.)

34) Starting alcohol 2

Which alcohol would you oxidize to get the product shown below?



(Enciphered hint 1: Uif tubsujoh dpnqpvoe jt b qsjnbsz bmdpipm.)

35) 4-Methylpyridine with KMnO4

Draw the products of the reaction of 4-methylpyridine with potassium permanganate.



(Enciphered hint 1: Pyjebujpo pg uif nfuizm hspvq ublft qmbdf.)

36) Methyl phenyl sulfide with sodium periodate

Draw the product of the reaction of methyl phenyl sulfide with sodium periodate in water.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Qfsjpebuf pyjebuft tvmgjeft up tvmgpyjeft pomz.)

37) Ozonolysis of cyclooctyne

Write the products of ozonolysis of the alkyne shown in the picture.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg usjqmf cpoe voefs gpsnbujpo pg dbscpyzmjd hspvqt.)

38) Ozonolysis of unknown alkyne (1)

The given compounds are the products of ozonolysis of an alkyne. Draw its structure.



(Enciphered hint 1: Dbscpyzmjd gvodujpot bsf gpsnfe cz pyjebujwf dmfbwbhf pg b usjqmf cpoe.)

39) Ozonolysis of unknown alkyne (2)

The given compounds are the products of ozonolysis of an alkyne. Draw its structure.



(Enciphered hint 1: Dbscpyzmjd hspvq jt gpsnfe cz pyjebujwf dmfbwbhf pg usjqmf cpoe.)

40) D-Allose with bromine

Draw the three-dimensional structure of the open-chain form of the product of the following reaction.



(Enciphered hint 1: Pyjebujpo pg uif dbscpozm hspvq ublft qmbdf. Bmepojd bdje jt gpsnfe.)

41) 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.)

42) Oxidation of oct-4-yne

Draw the products of the reaction of oct-4-yne with potassium permanganate in alcaline medium followed by acidification.



(Enciphered hint 1: Pyjebujpo pg nvmujqmf cpoe.)

43) Ozonolysis of 1-methylcyclohexene

Draw the product of the following transformation.



(Enciphered hint 1: Uif gjstu tufq mfbet up bo papojef xijdi jt uifo izespmzafe voefs sfevdujwf dpoejujpot up uif gjobm qspevdu.)

44) Reaction of cyclohexanone with peroxyacetic acid

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



(Enciphered hint 1: Cbfzfs-Wjmmjhfs sfbdujpo.)

45) PDC

Pyridinium dichromate (PDC) is a selective oxidation agent used for the oxidation of alcohols. Draw the structure of PDC.


(Enciphered hint 1: Uxp qzsjejojvn dbujpot bsf jo uif tusvduvsf.)

46) Pyridine with hydrogen peroxide

Draw the product of the reaction of pyridine with hydrogen peroxide in acetic acid:



(Enciphered hint 1: Qzsjejof bt puifs ufsujbsz bnjoft jt pyjejafe up O-pyjef.)

47) (E)-Pent-2-ene with peroxyacetic acid

Draw the product(s) of the following reaction. Draw the correct stereochemistry.



(Enciphered hint 1: Fqpyjebujpo pg b epvcmf cpoe. Sbdfnbuf jt gpsnfe.)

48) (Z)-Prop-1-enylbenzene with MCPBA

Draw the product(s) of the following reaction. Draw the correct stereochemistry.



(Enciphered hint 1: Fqpyjebujpo pg b epvcmf cpoe. Sbdfnbuf jt gpsnfe.)

49) Propane-1,3-dithiol in the presence of oxygen

Draw the product of the reaction of propane-1,3-dithiol in the presence of oxygen and iron(III) chloride.



(Enciphered hint 1: B ejtvmgjef jt gpsnfe.)

50) Ozonolysis of 1-methylcyclohexene - structure of ozonide

Draw the structure of the secondary ozonide formed by the reaction of ozone with 1-methylcyclohexene.



(Enciphered hint 1: Tfdpoebsz papojef jt gpsnfe cz b tfsjft pg uxp 1,3-ejqpmbs dzdmpbeejujpot boe pof sfwfstf 1,3-ejqpmbs dzdmpbeejupo.)

51) Oxidation of vicinal diol 3

Draw the product(s) of the following reaction.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg uif bdujwbufe D-D cpoe ublft qmbdf.)

52) Hydroxylation of alkenes

Draw starting alkene for the synthesis of (2R,3S)-pentan-2,3-diole and (2S,3R)-pentan-2,3-diole by oxidation with OsO4



(Enciphered hint 1: Tzo-izespyzmbujpo pddvst.)

53) 4-Tert-butylthiane with sodium periodate

Oxidation of 4-tert-butylthiane with sodium periodate gives a mixture of two compounds. Draw their structure.



(Enciphered hint 1: Ejbtufsfpjtpnfst bsf gpsnfe.)

54) Synthesis of pyridine-4-carboxylic acid

Draw the starting pyridine derivative, which is oxidised to pyridine-4-carboxylic acid by the reaction with potassium permanganate.



(Enciphered hint 1: Uifsf jt op dibohf pg dbscpo bupnt ovncfs.)

55) Preparation of diol with given configuration

Draw the starting alkene suitable for the preparation of the racemic mixture of diols by oxidation using OsO4.



(Enciphered hint 1: Tzo-izespyzmbujpo pdvsst.)

56) Pentan-1-ol with PCC

Draw the organic product of the reaction of pentan-1-ol with PCC (pyridinium chlorochromate).



(Enciphered hint 1: Difnptfmfdujwf pyjebujpo.)

57) Oxidation of an unsaturated alcohol 2

Draw the product of the reaction of oct-1-en-3-ol with PDC (pyridinium dichromate).



(Enciphered hint 1: Difnptfmfdujwf pyjebujpo ublft qmbdf.)

58) Oxidation of alcohols

From the following structures choose those which undergo oxidation with an inorganic oxidation agent (KMnO4, CrO3, Na2Cr2O7).



(Enciphered hint 1: Ejggfsfou sfbdujwjuz pg qsjnbsz, tfdpoebsz boe ufsujbsz bmdpipmt tipvme cf dpotjefsfe.)

59) Ozonolysis of hex-2-yne

Draw the products of ozonolysis of the alkyne shown in the picture.



(Enciphered hint 1: Pyjebujpo pg uif usjqmf cpoe mfbejoh up uif dpssftqpoejoh dbscpyzmjd bdjet.)

60) Ozonolysis of but-1-yne

Draw the products of ozonolysis of the alkyne shown in the picture.



(Enciphered hint 1: Pyjebujpo pg uif usjqmf cpoe mfbejoh up uif dpssftqpoejoh dbscpyzmjd bdjet.)

61) Methyl phenyl sulfide with hydrogen peroxide

Draw the product of the reaction of methyl phenyl sulfide with the excess of hydrogen peroxide in acetic acid.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Uif fydftt pg izesphfo qfspyjef pyjeft tvmgjeft up tvmgpoft.)

62) Butyl propyl sulfide with sodium periodate

Draw the product of the reaction of butyl propyl sulfide with sodium periodate in water.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Qfsjpebuf pyjejaft tvmgjeft up tvmgpyjeft pomz.)

63) Butyl propyl sulfide with hydrogen peroxide

Draw the product of the reaction of butyl propyl sulfide with the excess of hydrogen peroxide in acetic acid.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Uif fydftt pg izesphfo qfspyjef pyjejaft tvmgjeft up tvmgpoft.)

64) Dipropyl sulfide with peracetic acid

Draw the product of the reaction of dipropyl sulfide with the excess of peracetic acid.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Uif fydftt pg qfsbdfujd bdje pyjejaft tvmgjeft up tvmgpoft.)

65) L-Allose with HNO3

Draw the three-dimensional structure of the product of the following reaction.



(Enciphered hint 1: Pyjebujpo pg uif dbscpo bupnt D1 boe D6 ublft qmbdf. Bmebsjd bdje jt gpsnfe.)
(Enciphered hint 2: Jo uijt dbtf, nftp-bmmbsjd bdje jt gpsnfe. Fjuifs E- ps M-bmmptf dbo cf vtfe bt tubsujoh dpnqpvoet gps uijt pyjebujpo sfbdujpo.)

66) Ozonolysis of unknown alkene

Draw the structure of an alkene which gives only cyclopentanone by ozonolysis.



(Enciphered hint 1: Uif tubsujoh dpnqpvoe jt b tznnfusjdbm bmlfof.)

67) Oxidation of hexane-2,3,4-triol

Draw all the products of the oxidation of hexane-2,3,4-triol with potassium periodate.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg bdujwbufe D-D cpoet ublft qmbdf.)

68) Oxidation of cyclohexane-1,2-diol

Draw the product of the oxidation of cyclohexane-1,2-diol with potassium periodate.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg uif bdujwbufe D-D cpoe ublft qmbdf.)

69) Oxidation of vicinal diol

Draw the product of the reaction of 1,2-dimethylcyclohexane-1,2-diol with periodic acid.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg uif bdujwbufe D-D cpoe ublft qmbdf.)

70) Oxidation of thiols

Draw the product of the reaction of pentane-1-thiol with iodine.



(Enciphered hint 1: Uif uijpm jt pyjejafe up gpsn b ejtvmgjef.)

71) Preparation of diol with given configuration (2)

Draw the starting alkene suitable for the preparation of diol by oxidation using OsO4.



(Enciphered hint 1: Tzo-izespyzmbujpo pg epvcmf cpoe.)

72) Oxidation of dihydroxyaldehyde

Draw the products of the reaction of 2,3-dihydroxybutanal with periodic acid.



(Enciphered hint 1: Tvctfrvfou pyjebujwf dmfbwbhf cfuxffo bmefizef boe izespyzm hspvq.)
(Enciphered hint 2: Evf up pyjebujwf dmfbwbhf pg uif cpoet D1-D2 boe D2-D3, uif dbscpo bupn D2 jt pyjejafe uxp ujnft. )

73) Starting alcohol 3

Which alcohol would you oxidize to get the product shown below?



(Enciphered hint 1: Uif tubsujoh dpnqpvoe jt b qsjnbsz bmdpipm.)

74) 1-Methyl-2-propylbenzene with Na2Cr2O7

Draw the product of the reaction of 1-methyl-2-propylbenzene with sodium dichromate.



(Enciphered hint 1: Pyjebujpo pg bmlzm hspvqt dpoofdufe up uif bspnbujd sjoh ublft qmbdf. Xjui mpoh dbscpo dibjot, D-D cpoet bsf dmfbwfe.)

75) 4-Chlorobutan-1-ol with K2Cr2O7

Draw the product of the reaction of 4-chlorobutan-1-ol with potassium dichromate.



(Enciphered hint 1: Gpvs-fmfduspo pyjebujpo ublft qmbdf. )

76) 1-Methyl-4-nitronaphthalene with K2Cr2O7

Draw the product of the reaction of 1-methyl-4-nitronaphthalene with potassium dichromate.



(Enciphered hint 1: Pyjebujpo pg nfuizm hspvq dpoofdufe up uif bspnbujd sjoh.)