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1) Strength of acids 5

Choose the most acidic and the least acidic compound.



The most acidic phenol.


(Enciphered hint 1: Bdjejuz jt jodsfbtfe xjui uif qsftfodf boe uif ovncfs pg fmfduspo-xjuiesbxjoh hspvqt.)

The least acidic phenol.


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

2) Nomenclature III

Draw the structure of 2-methyl-2-propylpropane-1,3-diol.


(Enciphered hint 1: Bo bmjqibujd ejpm.)

3) 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.)

4) Butan-1-ol with hydrogen bromide

Draw the product of the reaction of butan-1-ol with hydrogen bromide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui cspnjef bojpo bdujoh bt uif ovdmfpqijmf. Bdjejd dpoejujpot bsf ofdfttbsz gps uif bdujwbujpo pg uif izespyz hspvq.)

5) (2R,3S)-Butane-2,3-diol

Draw the three-dimensional structural formula of (2R,3S)-butane-2,3-diol.


(Enciphered hint 1: Vtf xfehft boe ebtife mjoft up esbx cpoet up ofbsfs boe gvsuifs bupnt.)

6) Nucleophilic substitution on alcohols (mechanism)

During the following reaction of 3-methylbutan-2-ol with hydrogen bromide, the initially formed carbocation undergoes a rearrangement. Draw the structures of the starting and rearranged carbocations as well as the structure of the final product.



(Enciphered hint 1: Xbufs fmjnjobujpo.)


(Enciphered hint 1: I-tijgu gpsnjoh npsf tubcmf dbscpdbujpo.)


(Enciphered hint 1: Sfbdujpo pg dbscpdbujpo xjui ovdmfpqijmf.)

7) 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.)

8) Pentan-1-ol with SOCl2

Draw the organic product of the reaction of pentan-1-ol with thionyl chloride.



(Enciphered hint 1: Bmlzm ibmjeft bsf gpsnfe cz uif sfbdujpo pg bmdpipmt xjui ibmjeft pg jopshbojd bdjet.)

9) 4-Bromobutan-1-ol with NaH

What product will be formed by the reaction of 4-bromobutan-1-ol with sodium hydride?



(Enciphered hint 1: Jousbnpmfdvmbs ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

10) 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.)

11) 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.)

12) Dithiol in the presence of oxygen

Draw the product of the following reaction.



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

13) 2-Phenylethanol with TsCl

Draw 4-toluenesulfonyl chloride (tosylchloride, TsCl) and then the product of its reaction with 2-phenylethanol.


(Enciphered hint 1: Ju jt 4-nfuizmcfoafoftvmgpozm dimpsjef.)


(Enciphered hint 1: Uif sfbdujpot pg bmdpipmt xjui tvmgpozm dimpsjeft mfbe up ftufst pg tvmgpojd bdjet..)

14) 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.)

15) (2R,3R)-Butane-2,3-diol

Draw the three-dimensional structural formula of (2R,3R)-butane-2,3-diol.


(Enciphered hint 1: Vtf xfehft boe ebtife cpoet up esbx dpoofdujpot up ofbsfs boe gvsuifs bupnt. )

16) Butan-1-ol with potassium bromide

Draw the product of the reaction of butan-1-ol with potassium bromide in the presence of sulfuric acid.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui cspnjef bojpo bdujoh bt uif ovdmfpqijmf. Bdjejd dpoejujpot bsf ofdfttbsz gps uif bdujwbujpo pg uif izespyz hspvq.)

17) 1-Methylcyclopentanol with sulfuric acid

Draw all the organic products of the reaction of 1-methylcyclopentanol with sulfuric acid.



(Enciphered hint 1: Ufsujbsz bmdpipmt jo bdjejd nfejb sfbejmz gpsn dbscpdbujpot. Uif dbscpdbujpo uifo fmjnjobuft b qspupo. Uxp qspevdut dbo cf gpsnfe.)

18) Carbocation rearrangement during dehydration

During the following reaction, the initially formed carbocation undergoes a rearrangement. Draw the structures of the starting and rearranged carbocations.



(Enciphered hint 1: Qspupobujpo jt gpmmpxfe cz xbufs fmjnjobujpo.)


(Enciphered hint 1: Uif esjwjoh gpsdf pg uif sfbssbohfnfou jt uif gpsnbujpo pg npsf tubcmf dbscpdbujpo.)

19) Nomenclature XI

Draw the three-dimensional structural formula of (1R,2R,5S)-2-isopropyl-5-methylcyclohexane-1-thiol. Use wedged bonds to indicate the position of the substituents.


(Enciphered hint 1: B tpmje xfehf sfqsftfout cpoe upxbset uif sfbefs boe b ebtife mjof b sfdfejoh cpoe.)

20) Nucleophilic substitution on alcohols (mechanism)

Tertiary alcohols give readily alkyl halides on treatment with either HCl or HBr. The first step is protonation followed by loss of water. Fill in the structures of the intemediates for the reaction of 2-methylpentan-2-ol with hydrogen bromide.



(Enciphered hint 1: Bu gjstu, bdujwbujpo pg izespyz hspvq cz qspupobujpo ublft qmbdf.)


(Enciphered hint 1: Ufsujbsz bmdpipmt voefshp TO1 tvctujuvujpo. B dbscpdbujpo jt gpsnfe.)


(Enciphered hint 1: Uif dbscpdbujpo sfbdut xjui uif ovdmfpqijmf.)

21) Starting alcohol 1

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



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

22) Enantiomer 3

Draw a three-dimensional structural formula of the enantiomer of the compound shown.



(Enciphered hint 1: Bo foboujpnfs ibt uif pqqptjuf dpogjhvsbujpo po bmm uif tufsfpdfousft.)

23) 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. )

24) 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.)

25) Phenol oxidation

Draw the product of phenol oxidation with potassium dichromate.



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

26) Reaction of benzenesulfonic acid

Draw the product of the reaction of benzenesulfonic acid with sodium hydroxide at 300 °C.



(Enciphered hint 1: Uif sfqmbdfnfou pg uif -TP3I hspvq ublft qmbdf.)

27) 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.)

28) Structure to name (19)

Name the following structure:



(Enciphered hint 1: Ju jt b ejpm.)

29) Butan-1-ol with sodium

Draw the products of the reaction of butan-1-ol with sodium. Use the first box for the organic and the second box for the inorganic product.



(Enciphered hint 1: Tbmu efsjwfe gspn bmdpipm jt gpsnfe evsjoh uif sfbdujpo.)

(Enciphered hint 1: Npmfdvmbs izesphfo jt gpsnfe evsjoh uif sfbdujpo.)

30) Acid-base reaction 1

Draw the products of the reaction of phenol with hydroxide anion.



(Enciphered hint 1: qLb pg qifopm jt 10; qLb pg xbufs jt 15.8)

31) Cyclopentanol with p-TsCl

Draw the product of the following reaction.



(Enciphered hint 1: Bmlzm tvmgpobuf jt gpsnfe.)

32) 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.)

33) Butane-1,2,4-triol with p-toluenesulfonic acid

Draw the product of the reaction of (S)-butane-1,2,4-triol with catalytic amount of p-toluenesulfonic acid.



(Enciphered hint 1: Bo jousbnpmfdvmbs sfbdujpo ublft qmbdf.)

34) Dehydration of 1-methylcyclohexanol (mechanism)

Fill in the intermediates and products in the dehydration of 1-methylcyclohexanol by the action of sulfuric acid.



(Enciphered hint 1: Qspupobujpo pg uif izespyz hspvq tubsut uif nfdibojtn.)


(Enciphered hint 1: Uif dbscpdbujpo jt gpsnfe cz mptt pg xbufs.)


(Enciphered hint 1: Npsf tubcmf bmlfof jt uif nbkps qspevdu pg uif sfbdujpo.)

35) Starting alcohol 2

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



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

36) Diastereomer 2

Draw three-dimensional structural formulae of the diastereomers of the compound in the picture.



(Enciphered hint 1: B ejbtufsfpnfs jt b tufsfpjtpnfs xijdi jt opu foboujpnfs. Ju ejggfst jo uif dpogjhvsbujpo po pof ps npsf tufsfpdfousft, cvu opu po bmm pg uifn.)

37) Methanol with sodium

Draw the products (including inorganic ones) of the reaction of methanol with sodium.



(Enciphered hint 1: Sfepy sfbdujpo bobmphpvt up uif sfbdujpo pg tpejvn xjui xbufs.)

38) Preparation of thiols

Draw the products of the following reaction sequence.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)


(Enciphered hint 1: Bgufs cbtjd izespmztjt, uif qspevdu jt bdjejgjfe boe dpokvhbufe bdje jt gpsnfe. Ep opu gpshfu up esbx cpui pshbojd qspevdut.)

39) Thiophenolate with ethyliodide

Draw the product of the reaction of sodium benzenethiolate with ethyl iodide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

40) Fischer projection

Draw a three-dimensional structural formula of the given compound.



(Enciphered hint 1: Jo b Gjtdifs qspkfdujpo, bmm ipsjapoubm cpoet qspkfdu upxbset uif wjfxfs.)

41) Diastereomer

Draw three-dimensional structural formula of the diastereomers of the compound in the picture.



(Enciphered hint 1: B ejbtufsfpnfs jt b tufsfpjtpnfs xijdi jt opu foboujpnfs. Ju ejggfst jo uif dpogjhvsbujpo po pof ps npsf tufsfpdfousft, cvu opu po bmm pg uifn.)

42) Nomenclature VI

Draw the structure of 1-phenylpentan-1-ol.


(Enciphered hint 1: Nbjo dibjo (bmjqibujd) dpoubjot b izespyzm hspvq.)

43) 2-Phenylethanol with PBr3

Draw the product of the following reaction.



(Enciphered hint 1: Cspnjeft boe dimpsjeft pg jopshbojd tbmut bsf vtfe up usbotgfs bmdpipmt up bmlzm ibmjeft.)

44) 2-Phenylethanol with SOCl2

Draw the product of the following reaction.



(Enciphered hint 1: Cspnjeft boe dimpsjeft pg jopshbojd bdjet bsf vtfe up usbotgfs bmdpipmt up bmlzm ibmjeft.)

45) 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.)

46) Substitution with thiolate

Draw the product of the reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

47) 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.)

48) Pentan-1-ol with potassium bromide

Draw the organic product of the reaction of pentan-1-ol with KBr in the presence of sulfuric acid.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

49) Pinacol rearrangement 3 - mechanism

During dehydration of the vicinal diol shown below a carbocation is formed, which undergoes rearrangement. Draw the structure of the carbocation thus formed.



(Enciphered hint 1: B npsf tubcmf dbscpdbujpo jt gpsnfe wjb bmlzm sfbssbohfnfou. )

50) 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.)

51) 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.)

52) Ephedrine

Draw the structure of (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol.


(Enciphered hint 1: Vtf gvmm xfehf cpoe boe ebtife mjof up dpoofdu ofbsfs boe gvsuifs bupnt.)

53) Pseudoephedrine

Draw the structure of (1R,2R)-2-(methylamino)-1-phenylpropan-1-ol.


(Enciphered hint 1: Vtf gvmm xfehf cpoe boe ebtife mjof up dpoofdu ofbsfs boe gvsuifs bupnt.)

54) Absolute configuration 1

Draw the three-dimensional structural formula of (R)-butan-2-ol.


(Enciphered hint 1: Tufsfpeftdsjqups S tqfdjgjft uif dpogjhvsbujpo po b tufsfphfojd dfousf (ifsf b dbscpo bupn cfbsjoh gpvs ejggfsfou tvctujuvfout).)

55) Absolute configuration 2

Draw the three-dimensional structural formula of (S)-but-3-en-2-ol.


(Enciphered hint 1: Tufsfpeftdsjqups T tqfdjgjft uif dpogjhvsbujpo po b tufsfphfojd dfousf (ifsf b dbscpo bupn cfbsjoh gpvs ejggfsfou tvctujuvfout).)

56) Enantiomer

Draw a three-dimensional structural formula of the enantiomer of the compound in the picture.



(Enciphered hint 1: Bo foboujpnfs ibt bo pqqptjuf dpogjhvsbujpo po bmm uif tufsfphfojd dfousft.)

57) Pentan-1-ol with hydrogen chloride

Draw pentan-1-ol and then the product of its reaction with hydrogen chloride.


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


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui dimpsjef bojpo bdujoh bt uif ovdmfpqijmf. Bdjejd dpoejujpot bsf ofdfttbsz gps uif bdujwbujpo pg uif izespyz hspvq.)

58) 1-Methylcyclohexanol with sulfuric acid

Draw 1-methylcyclohexanol and then the major product of its reaction with sulfuric acid.


(Enciphered hint 1: Ufsujbsz bmdpipm.)


(Enciphered hint 1: Ufsujbsz bmdpipmt jo bdjejd nfejb sfbejmz gpsn dbscpdbujpot xijdi uifo fmjnjobuf b qspupo. Uif nbkps qspevdu jt gpsnfe bddpsejoh up uif [bjutfw't svmf.)

59) Butan-2-ol with H3PO4

Draw all organic products of the following reaction.



(Enciphered hint 1: Ufsujbsz boe tfdpoebsz bmdpipmt jo bdjejd nfejb gpsn dbscpdbujpot sfbejmz. Uif dbscpdbujpo uifo fmjnjobuft b qspupo. Uif nbkps qspevdu jt gpsnfe bddpsejoh up uif [bjutfw't svmf. Dpotjefs tufsfpjtpnfst.)

60) Alkyl halide from alcohol - all products

Draw all the products of the reaction of pentan-2-ol with thionyl chloride.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Esbx bmtp jopshbojd qspevdut.)

61) Alkyl halide from alcohol - PBr3

Draw the product of the reaction of cyclopentanol with phosphorus tribromide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

62) 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.)

63) Structure to name (2)

Name the following structure:



(Enciphered hint 1: Ju jt b dijsbm dpnqpvoe, ju jt ofdfttbsz up vtf Dbio-Johpme-Qsfmph qsjpsjuz svmft.)

64) Structure to name (5)

Name the following structure:



(Enciphered hint 1: Ju jt bo bmlpyzbmdpipm.)

65) Reactions of thiols 1

Draw the products (including inorganic ones) of the reaction of thiophenol with sodium hydroxide.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

66) 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.)

67) 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.)

68) Chlorophene

Draw the structure of 2-benzyl-4-chlorophenol.


(Enciphered hint 1: Cfoazm nfbot D6I5DI2- hspvq.)

69) Strength of acids 3

Choose the most acidic and the least acidic compound.



The least acidic compound.


(Enciphered hint 1: Bdjejuz jt jodsfbtfe cz uif qsftfodf boe uif ovncfs pg fmfduspo xjuiesbxjoh hspvqt.)

The most acidic compound.


(Enciphered hint 1: Bdjejuz jt jodsfbtfe cz uif qsftfodf boe uif ovncfs pg fmfduspo xjuiesbxjoh hspvqt.)

70) Reaction of thiol with alkene

Thiols react in radical additions similar to hydrogen bromides. Draw the product of the reaction of butane-1-thiol with hex-1-ene using dibenzoyl peroxide as the initiator.



(Enciphered hint 1: Sbejdbm beejujpo ublft qmbdf. Sfhjptfmfdujwjuz jt esjwfo cz uif gpsnbujpo pg uif npsf tubcmf sbejdbm.)

71) Pinacol rearrangement 2 - mechanism

During dehydration of 1,2-dimethylcyclohexane-1,2-diol a carbocation is formed, which undergoes rearrangement. This rearrangement yields two carbocations. Draw their structure.



(Enciphered hint 1: Uxp ejggfsfou bmlzm hspvqt dbo sfbssbohf.)

72) Pinacol rearrangement 1 - mechanism

During pinacol (2,3-dimethylbutane-2,3-diol) dehydration a carbocation is formed, which undergoes rearrangement. Draw the structure of the carbocation thus formed.



(Enciphered hint 1: B npsf tubcmf dbscpdbujpo jt gpsnfe wjb bmlzm sfbssbohfnfou.)

73) 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.)

74) 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.)