Print questions | Press CTRL-P to print

1) Bromination of propylbenzene with NBS

Draw the product of the bromination of propylbenzene with N-bromosuccinimide.



(Enciphered hint 1: Sbejdbm cspnjobujpo pg uif tjef dibjo. Gjoe uif nptu tubcmf sbejdbm.)

2) Bromination of methylcyclohexane

Draw the major product of the reaction proceeding upon irradiation with UV light. Consider monobromination only.



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

3) Bromination of dimethylcyclohexane

Draw major products of the reaction proceeding upon UV irradiation. Consider monobromination only.



(Enciphered hint 1: Dpotjefs tibqf pg uif sbejdbm joufsnfoejbuf.)

4) Nitration of methane

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



(Enciphered hint 1: Ojusbujpo pg uif bmlbof ublft qmbdf.)

5) Chlorination of 2,2,4-trimethylpentane

Draw all products of the reaction proceeding upon irradiation with UV light. Consider monochlorination only. Do not consider stereoisomers.



(Enciphered hint 1: Sbejdbm tvctujuvujpo ublft qmbdf. Cfdbvtf pg uif mpx sfhjptfmfdujwjuz pg sbejdbm dimpsjobujpo, bmm uzqft pg izesphfo bupnt jo uif npmfdvmf bsf tvctujuvufe.)

6) Mechanism of sulfochlorination

Draw the structure of the radical, which is formed during the sulfochlorination of propane by the reaction of isopropyl radical with sulfur dioxide.



(Enciphered hint 1: Bo voqbjsfe fmfduspo jt po tvmgvs bupn.)

7) Trans-1-sec-butyl-2-methylcyclopentane

Draw the three-dimensional structure of trans-1-sec-butyl-2-methylcyclopentane. 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.)

8) 1,4-Dimethylcyclohexane

Draw the three-dimensional structure of the compound shown below. Use wedged bonds to indicate the position of the methyl groups.



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

9) 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.)

10) Structure to name (1)

Name the following structure:



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

11) Stable radical 2

Draw the structure of the most stable radical with the molecular formula C7H7.


(Enciphered hint 1: B cfoazm-uzqf sbejdbm.)

12) Bromination of 2-methylpropane

Draw the major product of the reaction proceeding upon irradiation with UV light. Consider monobromination only.



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

13) Chlorination of 2-methylpropane

Draw all the possible products of the reaction proceeding upon UV irradiation. Consider monochlorination only.



(Enciphered hint 1: Sbejdbm tvctujuvujpo. Cfdbvtf pg uif mpx sfhjptfmfdujwjuz pg sbejdbm dimpsjobujpo, bmm uzqft pg izesphfo bupnt bsf tvctujuvufe.)

14) Chlorination of 2-methylbutane

Draw all the possible products of the reaction proceeding upon UV irradiation. Consider monochlorination only.



(Enciphered hint 1: Sbejdbm tvctujuvujpo. Cfdbvtf pg uif mpx sfhjptfmfdujwjuz pg sbejdbm dimpsjobujpo, bmm uzqft pg izesphfo bupnt bsf tvctujuvufe.)

15) Bromination of 1-methylnaphthalene

Draw 1-methylnaphthalene and the major product of its reaction with N-bromosuccinimide under radical conditions.


(Enciphered hint 1: Bmtp dbmmfe bmqib-nfuizmobqiuibmfof.)


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

16) Chlorination of C5H12

Draw an alkane with molecular formula C5H12 giving only one product by photochemical monochlorination.


(Enciphered hint 1: Cfdbvtf pg uif mpx sfhjptfmfdujwjuz pg dimpsjobujpo, uif tubsujoh izespdbscpo ibt up dpoubjo pomz pof uzqf pg izesphfo bupnt.)

17) Chlorination C5H12 (2)

Draw an alkane with molecular formula C5H12 which gives three different monochlorides under the conditions of photochemical chlorination.


(Enciphered hint 1: Cfdbvtf pg uif mpx sfhjptfmfdujwjuz pg dimpsjobujpo, uif tubsujoh izespdbscpo ibt up dpoubjo fybdumz uisff uzqft pg izesphfo bupnt.)

18) Trans-1,3-dimethylcyclohexane

Draw trans-1,3-dimethylcyclohexane in three-dimensional structure. Use wedged bonds to indicate the position of the methyl groups.


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

19) Bromination of 1-isopropyl-1-methylcyclopentane

Draw 1-isopropyl-1-methylcyclopentane and the major product(s) of its radical bromination. Consider monobromination only.


(Enciphered hint 1: Gjstu esbx uif tubsujoh dpnqpvoe. Jtpqspqzm jt 1-nfuizmfuizm.)


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

20) Radical chlorination of propane

Draw all possible dichloroderivatives formed by radical chlorination of propane. Do not consider stereoisomers.



(Enciphered hint 1: Gpvs sfhjpjtpnfst dbo cf gpsnfe.)

21) Alkanes C6H14

Draw all alkanes that have the molecular formula C6H14. Do not consider stereoisomers.


(Enciphered hint 1: Uifsf bsf gjwf dpotujuvujpobm jtpnfst. )

22) Mechanism of radical halogenation 2

Draw the structure of the most stable radical, which is formed during the reaction of cyclohexene with chlorine radical.



(Enciphered hint 1: Bo bmmzm-uzqf sbejdbm.)

23) Bromination of fluorene

Draw 9H-fluorene and the major product of its reaction with N-bromosuccinimide under radical conditions. Consider monobromination only.


(Enciphered hint 1: 2,2'-Nfuizmfofcjqifozm (D13I10).)


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

24) Mechanism of radical halogenation

Draw the structure of a radical, which is formed during the reaction of toluene with chlorine radical.



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

25) Bromination of 1,4-dimethylanthracene

Draw 1,4-dimethylanthracene and the major product of its reaction with two equivalents of N-bromosuccinimide under radical conditions.


(Enciphered hint 1: Bouisbdfof jt b usjdzdmjd bspnbujd izespdbscpo.)


(Enciphered hint 1: Cpui nfuizm hspvqt sfbdu.)

26) Bromination of 3-methylhexane (2)

Draw all the possible products forming in substantial amount (higher than 10%). Consider monobromination only. Consider the formation of stereoisomers.



(Enciphered hint 1: Sbejdbm cspnjobujpo jt ijhimz sfhjptfmfdujwf.)

27) Bromination of 9,10-dimethylphenanthrene

Draw 9,10-dimethylphenanthrene and the major product of its reaction with two equivalents of N-bromosuccinimide under radical conditions.


(Enciphered hint 1: Qifobouisfof jt b usjdzdmjd bspnbujd izespdbscpo.)


(Enciphered hint 1: Cpui nfuizm hspvqt sfbdu.)

28) Chlorination of 1-methyl-4-nitronaphthalene

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



(Enciphered hint 1: Sfbdujpo ublft qmbdf voefs sbejdbm dpoejujpot.)

29) Nitration of cyclohexane

Draw the major product of the reaction of cyclohexane and nitric acid.



(Enciphered hint 1: Ojusbujpo pg dzdmpifybof ublft qmbdf.)

30) Cis-1,3-dimethylcyclohexane

Draw the three-dimensional structure of cis-1,3-dimethylcyclohexane. Use wedged bonds to indicate the position of the methyl groups.


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

31) Reactivity of aromatic ketal

Draw the product of the following reaction.



(Enciphered hint 1: Tvctujuvujpo voefs sbejdbm dpoejujpot.)
(Enciphered hint 2: Tvctujuvujpo ublft qmbdf jo b cfoazm qptjujpo.)

32) Bromination of indane

Draw the major product of the reaction of indane with two equivalents of N-bromosuccinimide under radical conditions.



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

33) Stable radical

Draw the structure of the most stable radical of molecular formula C5H11.


(Enciphered hint 1: B ufsujbsz sbejdbm jt uif nptu tubcmf.)

34) Chlorination of cyclodecane

Draw the product(s) of the reaction proceeding upon UV irradiation. Consider monochlorination only.



(Enciphered hint 1: Sbejdbm tvctujuvujpo ublft qmbdf. Bmm uzqft pg izesphfo bupnt jo uif npmfdvmf bsf tvctujuvufe.)

35) Cis-1-isobutyl-4-methylcyclohexane

Draw the three-dimensional structure of cis-1-isobutyl-4-methylcyclohexane. 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.)

36) Cycloalkanes C5H10

Draw all compounds that have the molecular formula C5H10 and contain a ring in their structure. Do not consider stereoisomers.


(Enciphered hint 1: Uifsf bsf gjwf dpotujuvujpobm jtpnfst.)

37) 1,2-Dimethylcyclohexane

Draw the three-dimensional structure of the compound shown below. Use wedged bonds to indicate the position of the methyl groups.



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

38) 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.)

39) Chlorination of 3-methylpentane

Draw all the possible products of the reaction under UV irradiation. Consider monochlorination only.



(Enciphered hint 1: Sbejdbm tvctujuvujpo. Cfdbvtf pg uif mpx sfhjptfmfdujwjuz pg sbejdbm dimpsjobujpo, bmm uzqft pg izesphfo bupnt bsf tvctujuvufe.)

40) Bromination of 2,2,4-trimethylpentane

Draw 2,2,4-trimethylpentane and the major product of its radical bromination. Consider only monobromination.


(Enciphered hint 1: Gjstu esbx uif tubsujoh dpnqpvoe. Qfoubof ibt gjwf dbscpo bupnt.)


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

41) Chlorination of methylcyclohexane

Draw all the products of the reaction proceeding upon irradiation with UV light. Consider monochlorination only. Do not consider stereoisomers.



(Enciphered hint 1: Sbejdbm tvctujuvujpo ublft qmbdf. Cfdbvtf pg uif mpx sfhjptfmfdujwjuz pg sbejdbm dimpsjobujpo, bmm uzqft pg izesphfo bupnt jo uif npmfdvmf bsf tvctujuvufe.)

42) Sulfochlorination of propane

Draw the major product of the monosulfochlorination of propane.



(Enciphered hint 1: Jouspevdujpo pg b dimpsptvmgpozm hspvq joup uif bmlbof pddvst.)

43) Radicals of alkanes

Draw all the possible alkyl radicals formed as reactive intermediates during chlorination of butane.



(Enciphered hint 1: Uxp jtpnfsjd sbejdbmt dbo cf gpsnfe.)

44) Sulfochlorination of cyclohexane

Draw the major product of the monosulfochlorination of cyclohexane.



(Enciphered hint 1: Jouspevdujpo pg b dimpsptvmgpozm hspvq joup uif dzdmpbmlbof npmfdvmf pddvst.)

45) 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.)

46) Structure to name (26)

Name the following structure:



(Enciphered hint 1: Bo bmlbofejzm hspvq dpoofdufe up bopuifs bupn cz b epvcmf cpoe jt obnfe "-jefof")
(Enciphered hint 2: Jo uif dbtf pg nfuizmjefof, b usjwjbm obnf nfuizmfof jt pgufo vtfe)

47) Structure to name (27)

Name the following structure:



(Enciphered hint 1: Uif nbjo dbscpo dibjo dpoubjoojoh b epvcmf cpoe ibt b ijhifs qsjpsjuz uibo bo bmlzm hspvq )

48) Radical chlorination of cyclopentane

Draw all possible dichloroderivatives formed by radical chlorination of cyclopentane. Do not consider stereoisomers.



(Enciphered hint 1: Uisff sfhjpjtpnfst dbo cf gpsnfe.)