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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) Substitution reactions on 1-chloro-4-methoxy-2-methylbenzene

What product is formed by the reaction of 4-methoxy-2-methylchlorobenzene with N-bromosuccinimide in CCl4 and the presence of organic peroxides and then with sodium methanethiolate? The molecular formula of the final product is C9H11BrOS



(Enciphered hint 1: Gjstu, sbejdbm tvctujuvujpo pddvst.)


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

3) 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.)

4) 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.)

5) 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.)

6) 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.)

7) Nitration of methane

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



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

8) 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.)

9) 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.)

10) 4-Methylpyridine with NBS

Draw the product of the reactions of 4-methylpyridine with N-bromosuccinimide under radical conditions.



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

11) 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.)

12) 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.)

13) 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.)

14) 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.)

15) 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.)

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) 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.)

19) 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.)

20) 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.)

21) 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.)

22) 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.)

23) 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.)

24) 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.)

25) 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.)

26) 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.)

27) Nitration of cyclohexane

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



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

28) 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.)

29) 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.)

30) Stable radical

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


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

31) 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.)

32) 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.)

33) 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.)

34) 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.)

35) Sulfochlorination of propane

Draw the major product of the monosulfochlorination of propane.



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

36) 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.)

37) 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.)

38) 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.)