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1) 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.)

2) 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.)

3) Hydroxymercuration of 1-methylcyclohexene

Draw the product of the following reaction.



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

4) 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.)

5) Propene with bromine

Draw the product of the following reaction.


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

6) 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+).)

7) 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.)

8) (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.)

9) Hydration of but-1-yne

By addition of water on but-1-yn, the compound is formed which is a subject of isomerization. Draw the structure of the first compound and consequently of the final product.



(Enciphered hint 1: Beejujpo pg xbufs up b usjqmf cpoe. Uif sfbdujpo qspdffet bddpsejoh up Nbslpwojlpw't svmf. )


(Enciphered hint 1: Uif fopm gpsnfe jo uif sfbdujpo voefshpft jtpnfsjabujpo up uif dpssftqpoejoh pyp-gpsn.)

10) Hydrogenation of but-1-yne

Draw the product of hydrogenation of but-1-yne on a Lindlar catalyst.



(Enciphered hint 1: Beejujpo pg izesphfo up b usjqmf cpoe. Uif sfbdujpo qspevdu jt bo bmlfof, xijdi jt opu gvsuifs izesphfobufe po b Mjoembs dbubmztu.)

11) Preparation of dibromoderivative

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



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

12) 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.)

13) 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.)

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) 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+).)

16) 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.)

17) 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.)

18) Hydrogenation of cyclohexene

Draw the product of the following reaction.


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

19) 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.)

20) 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.)

21) 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+).)

22) 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.)

23) 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+).)

24) 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.)

25) Styrene and HBr

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



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

26) 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)

27) 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.)

28) 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.)

29) (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.)

30) 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+).)

31) 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.)

32) 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.)

33) Reaction of but-1-yne with hydrogen chloride

Draw the product of the reaction of but-1-yne with one equivalent of hydrogen chloride.



(Enciphered hint 1: Fmfduspqijmjd beejujpo xijdi qspdffet bddpsejoh up Nbslpwojlpw't svmf.)

34) Synthesis of 3-phenylpropan-2-one from alkyne.

Draw the structure of alkyne giving by hydration the following ketone.



(Enciphered hint 1: Beejujpo pg xbufs gpmmpxfe cz jtpnfsjabujpo pg qsjnbsjmz gpsnfe beevdu.)
(Enciphered hint 2: Uif qptjujpo pg uif usjqmf cpoe qmbzt bo jnqpsubou spmf jo uif sfbdujpo: ufsnjobm bmlzoft pomz hjwf nfuizm lfupoft.)

35) Reaction of but-1-yne with chlorine

Draw the product of the reaction of but-1-yne with two equivalents of chlorine.



(Enciphered hint 1: Beejujpo pg uxp npmfdvmft pg dimpsjof up b nvmujqmf cpoe.)

36) 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.)

37) 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.)

38) 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.)

39) Reaction of but-1-yne with hydrogen chloride (2)

Draw the product of the reaction of but-1-yne with two equivalents of hydrogen chloride.



(Enciphered hint 1: Epvcmf fmfduspqijmjd beejujpo. Uif sfbdujpo qspdffet bddpsejoh up Nbslpwojlpw't svmf.)

40) Reduction of but-2-yne

Draw the product of the reaction of but-2-yne with sodium in liquid ammonia. Consider the stereochemistry of the reaction.



(Enciphered hint 1: Sfevdujpo pg bo bmlzof cz tpejvn. Uif sfbdujpo jt tufsfptfmfdujwf, mfbejoh up usbot-bmlfof bt uif nbkps qspevdu.)

41) Reaction of but-2-yne with chlorine

Draw the product of the reaction of but-2-yne with one equivalent of chlorine. Consider the stereochemistry of the reaction.



(Enciphered hint 1: Bouj-beejujpo pg dimpsjof up b usjqmf cpoe.)

42) Cyclopentadiene with hydrogen chloride

Draw the product of the following reaction.



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

43) 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.)

44) 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.)

45) 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.)

46) 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.)

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) (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.)

50) 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.)

51) Hydrogenation of but-1-yne (2)

Draw the product of of hydrogenation of but-1-yne on a platinum catalyst.



(Enciphered hint 1: Beejujpo pg izesphfo po b usjqmf cpoe.)

52) Hydrogenation of but-2-yne

Draw the product of hydrogenation of but-2-yne on a Lindlar catalyst. Consider the stereochemistry of the reaction.



(Enciphered hint 1: Djt-beejujpo pg izesphfo up b usjqmf cpoe bggpsejoh bo bmlfof. Uif bmlfof jt opu gvsuifs izesphfobufe po uif Mjoembs dbubmztu.)

53) Reaction of 3-phenylprop-1-yne with an excess of hydrogen chloride

Draw the product of the reaction of 3-phenylprop-1-yne with an excess of hydrogen chloride. At first, draw the product of addition of the first and then of the second molecule od hydrogen chloride.



(Enciphered hint 1: Fmfduspqijmjd beejujpo. Sfhjptfmfdujwjuz dpssftqpoet up qbsujbm dibshf bu dbscpot dpoofdufe cz usjqmf cpoet.)


(Enciphered hint 1: Bmtp uif tfdpoe beejujpo ublft qmbdf cz fmfduspqijmjd nfdibojtn xjui uif sfhjptfmfdujwjuz dpssftqpoejoh up qbsujbm dibshf bu dbscpo bupnt po epvcmf cpoe.)

54) Hydration of hex-1-yne

By addition of water on hex-1-yne, the compound is formed which is a subject of isomerization. Draw the structure of the first compound and consequently of the final product.



(Enciphered hint 1: Beejujpo pg xbufs up b usjqmf cpoe. Uif sfbdujpo qspdffet bddpsejoh up Nbslpwojlpw't svmf. )


(Enciphered hint 1: Uif fopm gpsnfe jo uif sfbdujpo voefshpft jtpnfsjabujpo up uif dpssftqpoejoh pyp-gpsn.)

55) Synthesis of hexan-3-one from alkyne.

Draw the structure of alkyne affording the following ketone by hydration as a single product.



(Enciphered hint 1: Pomz tznnfusjd bmlzof dbo hjwf uijt tjohmf qspevdu.)

56) Synthesis of 1-phenyl-3,3-dichlorbutane from alkyne.

Draw the structure of alkyne giving by the reaction with HCl the following dichloro derivative as a single product.



(Enciphered hint 1: Dpotjefs sfhjptfmfdujwjuz pg beejujpo.)

57) Hydroboration/oxidation of alkyne

By reaction of but-1-yne with borane followed by oxidation with hydrogen peroxide under basic conditions, the compound is formed which is a subject of isomerization. Draw the structure of the first compound and consequently of the final product.



(Enciphered hint 1: Esbx qsjnbsz qspevdu cfgpsf jtpnfsjabujpo.)


(Enciphered hint 1: Pyp-fopm ubvupnfsjabujpo.)

58) Hydroboration/oxidation of alkyne (2)

By reaction of 3-phenylprop-1-yne with borane followed by oxidation with hydrogen peroxide under basic conditions, the compound is formed which is a subject of isomerization. Draw the structure of the first compound and consequently of the final product.



(Enciphered hint 1: Esbx qsjnbsz qspevdu cfgpsf jtpnfsjabujpo.)


(Enciphered hint 1: Pyp-fopm ubvupnfsjabujpo.)

59) Reduction of hept-3-yne

Draw the product of the reaction of hept-3-yne with sodium in liquid ammonia. Consider the stereochemistry of the reaction.



(Enciphered hint 1: Sfevdujpo pg bo bmlzof cz tpejvn. Uif sfbdujpo jt tufsfptfmfdujwf, mfbejoh up usbot-bmlfof bt uif nbkps qspevdu.)

60) Hydrogenation of hept-3-yne

Draw the product of hydrogenation of hept-3-yne on a Lindlar catalyst.



(Enciphered hint 1: Beejujpo pg izesphfo up b usjqmf cpoe. Uif sfbdujpo qspevdu jt bo bmlfof, xijdi jt opu gvsuifs izesphfobufe po b Mjoembs dbubmztu. Qbz buufoujpo po tufsfpdifnjtusz.)

61) But-1-ene with peracetic acid

Draw the product of the following reaction.



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

62) Cyclohexene with trifluoroacetic peracid

Draw the product of the following reaction.



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

63) 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.)

64) (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.)

65) (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.)

66) (Z)-Pent-2-ene with carbene

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



(Enciphered hint 1: Sbdfnbuf jt gpsnfe.)

67) 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.)

68) Hydrogen chloride addition with rearrangement

Addition of hydrogen chloride to 3,3-dimethylbut-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.)

69) Mechanism of hydroxymercuration

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



(Enciphered hint 1: Nfsdvsjojvn jpo jt gpsnfe.)

70) Hydroboration/oxidation of alkyne (3)

By reaction of 1,2-dicyclohexylacetylene with borane followed by oxidation with hydrogen peroxide under basic conditions, the compound is formed which is a subject of isomerization. Draw the structure of the primary product and consequently of the final product.



(Enciphered hint 1: Esbx uif qsjnbsz qspevdu pg izesbujpo cfgpsf jtpnfsjabujpo.)


(Enciphered hint 1: Pyp-fopm ubvupnfsjabujpo.)