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1) E,Z isomerism 3

Draw the structural formula of (E)-oct-4-ene.


(Enciphered hint 1: Uif F tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

2) Reduction of (E)-oct-2-en-4-yne

Draw the product of the reaction of (E)-oct-2-en-4-yne with hydrogen using the Lindlar catalyst. Consider the configuration of the product.



(Enciphered hint 1: Dpotjefs difnptfmfdujwjuz pg izesphfobujpo xjui uif Mjoembs dbubmztu.)

3) Maleinanhydride with buta-1,3-diene

Draw maleinanhydride and the product(s) of its reaction with buta-1,3-diene.


(Enciphered hint 1: Boizesjef pg ([)-cvufopjd bdje.)


(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

4) 7-oxa[2.2.1]hept-2-ene

Draw the starting compounds for the preparation of 7-oxa[2.2.1]hept-2-ene by the Diels-Alder reaction.



(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

5) Cyclohexene with carbene

Draw the product of the following reaction.



(Enciphered hint 1: Dbscfof jt hfofsbufe boe uifo ju jt beefe up b epvcmf cpoe.)

6) E,Z isomerism 6

Draw the structural formula of (Z)-3-bromo-3-chloro-2-(trifluoromethyl)prop-2-en-1-ol.


(Enciphered hint 1: Uif [ tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

7) Allyl carbocation 3

Draw the resonance structure of the following carbocation.



(Enciphered hint 1: Sftpobodf tusvduvsf jt dsfbufe cz npwjoh qj fmfduspot ps gsff fmfduspo qbjs upxbset uif qptjujwf dibshf.)

8) Hydroxymercuration of 1-methylcyclohexene

Draw the product of the following reaction.



(Enciphered hint 1: Bo bmdpipm jt gpsnfe bddpsejoh Nbslpwojlpw svmf.. )

9) Mechanism of hydroxymercuration and demercuration

Draw the structure of the cation intermediate of the following reaction. Cyclic cation is opened by water and the adduct is reduced by sodium tetrahydridoborate. Complete scheme.



(Enciphered hint 1: Uisff-nfncfsfe nfubmmbdzdmf jt gpsnfe.)


(Enciphered hint 1: Nfubmmbdzdmf jt pqfofe cz xbufs bu npsf tvctujuvufe dbscpo bupn.)


(Enciphered hint 1: Gjobm qspevdu jt gpsnfe cz sfevdujpo pg Ih-D cpoe. Nfsdvsz jt gpsnfe bt b cz-qspevdu.)

10) Propene with bromine

Draw the product of the following reaction.


(Enciphered hint 1: Fmfduspqijmjd cspnjobujpo pg b epvcmf cpoe.)

11) 1-Methylcyclohexene with water under acidic conditions

Draw the product of the reaction of 1-methylcyclohexene with diluted sulfuric acid.


(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif nptu tubcmf dbscpdbujpo vqpo uif sfbdujpo xjui bo fmfduspqijmf (I+).)

12) Propene with bromine in water

Draw the product of the following reaction.


(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt hjwfo cz b qbsujbm qptjujwf dibshf po pof dbscpo bupn pg uif uisff-nfncfsfe sjoh pg b cspnpojvn dbujpo.)

13) (Z)-hex-2-ene with bromine

Draw the three-dimensional structure of the product(s) of the following reaction.


(Enciphered hint 1: Fmfduspqijmjd usbot-beejujpo up b epvcmf cpoe. Sbdfnjd njyuvsf pg pof ejbtufsfpjtpnfs jt gpsnfe.)

14) 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.)

15) But-2-yne with 2-methylbuta-1,3-diene

Draw the product of the following reaction.



(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

16) E,Z isomerism 2

Draw the structural formula of (E)-2,3-dichlorohex-2-ene.


(Enciphered hint 1: Uif F tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

17) Preparation of dibromoderivative

Draw the starting alkene suitable for the preparation of dibromoderivative using bromine.



(Enciphered hint 1: Bouj-beejujpo pg cspnjof.)

18) Preparation of 1,2-dimethylcyclohex-1-ene

Draw the starting compounds for the preparation of 1,2-dimethylcyclohex-1-ene by the Diels-Alder reaction.



(Enciphered hint 1: Esbx uif tubsujoh ejfof boe ejfopqijmf (bmlfof).)

19) 1-Methylcyclohexene with bromine in water

Draw the product of the following reaction. Draw all stereoisomers formed by this reaction.



(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt hjwfo cz b qbsujbm qptjujwf dibshf po pof dbscpo bupn pg uif uisff-nfncfsfe sjoh pg b cspnpojvn dbujpo.)

20) Benzoquinone with buta-1,3-diene

Draw the product of the reaction between p-benzoquinone and one equivalent of buta-1,3-diene.



(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo pg b ejfof xjui b ejfopqijmf.)

21) (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.)

22) E,Z isomerism 5

Draw the structural formula of (E)-3-tert-butylpent-3-en-1-ol.


(Enciphered hint 1: Uif F tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

23) Cyclohexene with N-bromosuccinimide

Draw the product of the reaction of cyclohexene with N-bromosuccinimide in carbon tetrachloride.


(Enciphered hint 1: Sbejdbm tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif nptu tubcmf sbejdbm.)

24) Propene with chlorine under radical conditions

Draw the product of the reaction of propene with chlorine under radical conditions (450 °C).


(Enciphered hint 1: Sbejdbm tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif nptu tubcmf sbejdbm.)

25) 1-Methylcyclohexene with hydrogen bromide

Draw the product of the following reaction.


(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif nptu tubcmf dbscpdbujpo vqpo uif sfbdujpo xjui bo fmfduspqijmf (I+).)

26) 1-Methylcyclohexene with hydrogen bromide under radical conditions

Draw the product of the reaction of 1-methylcyclohexene with hydrogen bromide in the presence of organic peroxides.


(Enciphered hint 1: Sbejdbm beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg b npsf tubcmf sbejdbm vqpo uif sfbdujpo pg uif tvctusbuf xjui cspnjof sbejdbm.)

27) 2-Methylpropene under acidic conditions

Draw structure of carbocation formed primarily by the reaction of 2-methylpropene with aqueous sulphuric acid.



(Enciphered hint 1: Npsf tubcmf dbscpdbujpo jt gpsnfe.)

28) Hydrogenation of cyclohexene

Draw the product of the following reaction.


(Enciphered hint 1: Beejujpo pg izesphfo up b epvcmf cpoe.)

29) 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.)

30) 2-Tert-butyl-3,3-dimethylbut-1-ene with diborane

Draw the product of the hydroboration-oxidation of 2-tert-butyl-3,3-dimethylbut-1-ene.



(Enciphered hint 1: Sfhjptfmfdujwjuz jt hjwfo cz uif beejujpo pg cpsbof up uif epvcmf cpoe.)

31) Mechanism of hydroxymercuration

Draw the structure of the cation intermediate of the following reaction.



(Enciphered hint 1: Nfsdvsz bupn jo bo joufsnfejbuf jt qpttjujwfmz dibshfe.)

32) Pent-1-ene with hydrogen bromide

Draw the product of the following reaction.


(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif nptu tubcmf dbscpdbujpo vqpo uif sfbdujpo xjui bo fmfduspqijmf (I+).)

33) 2-Methylbuta-1,3-diene with ethene

Draw the product of the following reaction.



(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

34) 2,3-Dimethylbuta-1,3-diene with hydrogen chloride - high temperature

Draw the product of the reaction of 2,3-dimethylbuta-1,3-diene with hydrogen chloride at higher temperature.



(Enciphered hint 1: Bu ijhifs ufnqfsbuvsf, uif sfbdujpo jt uifsnpezobnjdbmmz dpouspmmfe. Uifsfgpsf, 1,4-beejujpo qsfepnjobuft pwfs 1,2-beejujpo.)

35) 1,4-Dimethylcyclohex-1-ene with water under acidic conditions

Draw the product of the reaction of 1,4-dimethylcyclohex-1-ene with diluted sulfuric acid.



(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg b npsf tubcmf dbscpdbujpo evsjoh uif sfbdujpo xjui fmfduspqijmf (I+).)

36) Propene with bromine in methanol

Draw the product of the following reaction.



(Enciphered hint 1: Qsjnbsjmz gpsnfe cspnpojvn jpo jt pqfofe cz uif buubdl pg nfuibopm.)

37) Styrene and HBr

Draw cationic intermediate formed during the reaction of HBr with styrene.



(Enciphered hint 1: Uif nptu tubcmf dbscpdbujpo jt gpsnfe.)

38) 1-Methylcyclohexene with diborane

Draw the product of the following reaction. Draw the correct stereochemistry.



(Enciphered hint 1: Sfhjptfmfdujwjuz jt hjwfo cz uif beejujpo pg cpsbof up uif epvcmf cpoe.)
(Enciphered hint 2: Cpui, uif cpspo boe uif izesphfo bee tjnvmubofpvtmz po uif tbnf gbdf pg uif epvcmf cpoe)

39) 1-Tert-butyl-4-methylidenecyclohexane with diborane

Hydroboration-oxidation of 1-tert-butyl-4-methylidenecyclohexane gives two products. Draw their structure.



(Enciphered hint 1: Njyuvsf pe ejbtufsfpjtpnfst jt gpsnfe.)

40) Mechanism of cyclohexene bromination

Draw the structure of bromonium cation formed during the bromination of cyclohexene. Indicate relative configuration.



(Enciphered hint 1: Jo b cspnpojvn dbujpo uxp tjhnb cpoet bsf gpsnfe cfuxffo cspnjof bupn boe uxp bekbdfou dbscpo bupnt.)

41) But-1-ene with MCPBA

Draw all products of the following reaction.



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

42) (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.)

43) Propene with hydrogen bromide

Draw the product of the following reaction.


(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif nptu tubcmf dbscpdbujpo vqpo uif sfbdujpo xjui bo fmfduspqijmf (I+).)

44) Hydrogenation of 1,2-dimethylcyclohexene

Draw the product of the following reaction. Show the relative configuration of the product.


(Enciphered hint 1: Djt-beejujpo pg izesphfo up b epvcmf cpoe.)

45) Pent-1-ene with hydrogen bromide under radical conditions

Draw the product of the reaction of pent-1-ene with hydrogen bromide in the presence of organic peroxides.


(Enciphered hint 1: Sbejdbm beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif npsf tubcmf sbejdbm vqpo uif sfbdujpo pg uif bmlfof xjui cspnjof sbejdbm.)

46) E,Z isomerism 4

Draw the structural formula of (E)-2-(bromomethyl)-3-methylhept-2-enal.


(Enciphered hint 1: Uif F tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

47) Allyl carbocation 1

Draw the resonance structure of the following carbocation.



(Enciphered hint 1: Sftpobodf tusvduvsf jt gpsnfe cz npwjoh qj fmfduspot ps gsff fmfduspo qbjs upxbset uif qptjujwf dibshf.)

48) 2,3-Dimethylbuta-1,3-diene with hydrogen chloride - low temperature

Draw the product of the reaction of 2,3-dimethylbuta-1,3-diene with hydrogen chloride at low temperature.



(Enciphered hint 1: Bu mpx ufnqfsbuvsf, uif sfbdujpo jt ljofujdbmmz dpouspmmfe. Uifsfgpsf, 1,2-beejujpo qsfepnjobuft pwfs 1,4-beejujpo.)

49) Ethylene

Draw the structure of ethylene.


(Enciphered hint 1: Usjwjbm obnf pg fuifof.)

50) 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.)

51) Propene with hydrogen bromide under radical conditions

Draw the product of the reaction between propene and hydrogen bromide in the presence of organic peroxides.


(Enciphered hint 1: Sbejdbm beejujpo up b epvcmf cpoe. Sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg b npsf tubcmf sbejdbm vqpo uif sfbdujpo pg uif bmlfof xjui cspnjof sbejdbm.)

52) Cyclohexene with bromine

Draw the product of the following reaction. Draw the relative configuration of the product.



(Enciphered hint 1: Fmfduspqijmjd beejujpo up b epvcmf cpoe. Cspnjobujpo jt b usbot beejujpo.)

53) Prop-2-enal with buta-1,3-diene

Draw the product of the following reaction.



(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

54) Allyl carbocation 2

Draw the resonance structure of the following carbocation.



(Enciphered hint 1: Sftpobodf tusvduvsf jt dsfbufe cz npwjoh qj fmfduspot ps gsff fmfduspo qbjs upxbset uif qptjujwf dibshf.)

55) Preparation of diethyl trans-4,5-dimethylcyclohex-4-ene-1,2-dicarboxylate

Draw diethyl trans-4,5-dimethylcyclohex-4-ene-1,2-dicarboxylate and suggest the starting compounds for its preparation by the Diels-Alder reaction.


(Enciphered hint 1: Ejfuizm ftufs pg ejdbscpyzmjd bdje.)

The suggested starting compounds:


(Enciphered hint 1: Esbx uif tubsujoh ejfof boe ejfopqijmf (bmlfof). Qbz buufoujpo up uif dpogjhvsbujpo pg uif tubsujoh bmlfof.)

56) 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.)

57) Cyclopentadiene with hydrogen chloride

Draw the product of the following reaction.



(Enciphered hint 1: Uif sfbdujpo qspdffet wjb uif npsf tubcmf bmmzmjd dbscpdbujpo.)

58) E,Z isomerism 1

Draw the structural formula of (Z)-3,4-dimethylhex-3-ene.


(Enciphered hint 1: Uif [ tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

59) Dimethyl bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate

Draw the starting compounds for the preparation of dimethyl bicyclo[2.2.1]hepta-2,5-diene-2,3-dicarboxylate by the Diels-Alder reaction.



(Enciphered hint 1: Esbx uif tubsujoh ejfof boe ejfopqijmf (bmlfof).)

60) Reaction of but-1-ene with chlorine (2)

Draw both enantiomers of the product formed by the reaction of but-1-ene with one equivalent of chlorine.



(Enciphered hint 1: Foboujpnfst ejggfst cz uif dpogjhvsbujpo po tufsfphfojd dfoufs.)

61) Reduction of hex-1-en-4-yne

Draw the product of the reaction of hex-1-en-4-yne with hydrogen with Lindlar catalyst. Consider the configuration of the product.



(Enciphered hint 1: Dpotjefs difnp- boe tufsfp-tfmfdujwjuz pg izesphfobujpo xjui uif Mjoembs dbubmztu.)

62) Stereoselectivity of bromine addition

Racemic mixture of (2S,3S)-dibrompentane and (2R,3R)-dibrompentane is formed by bromine addition to an alkene. Draw its structure.



(Enciphered hint 1: Bouj-beejujpo pg cspnjof.)

63) 1-Methylcyclohexene with dimethyl borane (2)

Draw the product of the following reaction. Specify configuration.



(Enciphered hint 1: Usjbmlzmcpsbof jt gpsnfe. Sfhjptfmfdujwjuz dpssftqpoet up uif qpmbsjabujpo pg b epvcmf cpoe.)

64) Diethyl fumarate with buta-1,3-diene

Draw diethyl fumarate and the product(s) of its reaction with buta-1,3-diene.


(Enciphered hint 1: Ejfuizm (F)-cvu-2-foejpbuf)


(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo jt tufsfptqfdjgjd.)

65) (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.)

66) (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.)

67) 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.)

68) 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.)

69) (Z)-Hex-3-ene with carbene

Draw the three-dimensional formulae of product(s) of the following reaction. 



(Enciphered hint 1: Tzo beejujpo pg dbscfof.)

70) Propene with N-bromosuccinimide

Draw the product of the reaction of propene with N-bromosuccinimide in carbon tetrachloride.



(Enciphered hint 1: Sbejdbm tvctujuvujpo. Uif sfhjptfmfdujwjuz jt ejsfdufe cz uif gpsnbujpo pg uif nptu tubcmf sbejdbm.)

71) 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.)

72) Hydrogen chloride addition with rearrangement (1)

Addition of hydrogen chloride to 3-methylbut-1-ene gives, because of rearrangement of carbocationic intermediate, a mixture of isomeric chlorides. Draw structure of carbocations and final chlorides



(Enciphered hint 1: Dbscpdbujpo gpsnfe cz qspupo beejujpo up b epvcmf cpoe voefshpft sfbssbohfnfou cz nfuizm tijgu.)


(Enciphered hint 1: Cpui dbscpdbujpot sfbdu xjui dimpsjef jpo.)

73) Pent-1-en-4-yne

Draw the structure of pent-1-en-4-yne.


(Enciphered hint 1: Opuf uif qptjujpo pg nvmujqmf cpoet.)

74) But-1-ene with peracetic acid

Draw the product of the following reaction.



(Enciphered hint 1: Fqpyjebujpo pg uif epvcmf cpoe pddvst.)

75) Cyclohexene with trifluoroacetic peracid

Draw the product of the following reaction.



(Enciphered hint 1: Fqpyjebujpo pg uif epvcmf cpoe pddvst.)

76) Pent-1-ene with m-chloroperbenzoic acid

Draw the three-dimensional formulae of products of the following reaction. 



(Enciphered hint 1: Fqpyjebujpo pg uif epvcmf cpoe ublft qmbdf gpsnjoh b dijsbm dfoufs.)

77) (Z)-Pent-2-ene with peracetic acid

Draw the three-dimensional formulae of products of the following reaction. 



(Enciphered hint 1: Fqpyjebujpo pg uif epvcmf cpoe ublft qmbdf gpsnjoh uxp dijsbm dfoufst.)
(Enciphered hint 2: Dpogjhvsbujpot pg uiftf dfoufst bsf cbtfe cpui po uif dpogjhvsbujpo pg uif tubsujoh bmlfof boe tzo-nfdibojtn pg fqpyjebujpo.)

78) (E)-Hept-3-ene with peracetic acid

Draw the three-dimensional formulae of products of the following reaction. 



(Enciphered hint 1: Fqpyjebujpo pg uif epvcmf cpoe ublft qmbdf gpsnjoh uxp dijsbm dfoufst.)
(Enciphered hint 2: Dpogjhvsbujpot pg uiftf dfoufst bsf cbtfe cpui po uif dpogjhvsbujpo pg uif tubsujoh bmlfof boe tzo-nfdibojtn pg fqpyjebujpo.)