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1) p-Bromobenzyl bromide with sodium cyanide

Draw p-bromobenzyl bromide and the product of its reaction with sodium cyanide.

(Enciphered hint 1: 1-cspnp-4-(cspnpnfuizm)cfoafof)


(Enciphered hint 1: TO2 tvctujuvujpo pddvst)

2) Oxirane with methylmagnesium iodide

Draw the product of the following reaction.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

3) Triphenylmethylphosphonium-jodide

Draw triphenylphosphine and product of its reaction with methyl iodide.

(Enciphered hint 1: Qiptqibof efsjwbujwf.)


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Qiptqipsvt bupn jt ovdmfpqijmf.)

4) Preparation of ylide

Draw the product of the reaction of triphenylphosphine with ethyl bromide and the product of the successive reaction with butyllithium.



(Enciphered hint 1: Usjqifozmqiptqijof sfbdut bt ovdmfpqijmf.)


(Enciphered hint 1: Uif nptu bdjejd izesphfo jt mptu.)

5) Allyl bromide with sodium isopropoxide

Draw the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui jtpqspqpyjef bojpo bdujoh bt uif ovdmfpqijmf.)

6) 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.)

7) 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.)

8) Hexan-2-yl p-toluenesulfonate with sodium benzenthiolate

Draw three-dimensional formula of the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo qspdffejoh wjb TO2 nfdibojtn. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo.)

9) 2-Bromopentane with ethanol

Draw the three-dimensional structural formula of (S)-2-bromopentane and product(s) of its solvolysis in ethanol.




(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo qspdffejoh wjb TO1 nfdibojtn. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo.)

10) 2,2,3-Trimethyloxirane with methanol

Draw the major product of the following reaction.



(Enciphered hint 1: Usfbujoh b qspupobufe fqpyjef xjui ovdmfpqijmf mfbet up uif sjoh pqfojoh. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo. Qbz buufoujpo up uif sfhjptfmfdujwjuz pg uif sfbdujpo.)

11) Gabriel synthesis 2

The Gabriel synthesis is used for preparation of primary amines using potassium phthalimide. First draw the organic product of phthalimide alkylation by 3,5-dibromobenzyl bromide and then the products after reaction of the alkylated phthalimide with hydrazine.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)


(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo. Bo bnjof boe b izesbajef bsf gpsnfe.)

12) 1-Bromobutan-2-ol with sodium hydroxide

Draw the product of the following reaction.



(Enciphered hint 1: Jousbnpmfdvmbs ovdmfpqijmjd tvctujuvujpo.)

13) Phosphonium salt 3

Draw the product of the reaction of methyl triphenyl phosphonium bromide with dimsyl sodium (sodium salt of dimethylsulfoxide).



(Enciphered hint 1: Bdje-cbtf sfbdujpo. Bo zmjef jt gpsnfe.)

14) 2-Bromo-1-phenylbutane with sodium iodide 2

Draw the three-dimensional structural formula of (R)-2-bromo-1-phenylbutane and the product of its reaction with sodium iodide in acetone.

(Enciphered hint 1: Difdl dpogjhvsbujpo po tufsfphfojd dfoufs.)


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo qspdffejoh wjb TO2 nfdibojtn. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo.)

15) 2-Bromopentane with sodium ethoxide

Draw all possible products of the reaction of 2-bromopentane with sodium ethoxide. Consider both substitution and elimination.


(Enciphered hint 1: Cpui tvctujuvujpo boe fmjnjobujpo qspdffe bt dpnqfujujwf sfbdujpot.)

16) 2-Phenyloxirane with methylmagnesium bromide

Draw the product of the following reaction.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

17) 1-Bromo-2-phenylethane with sodium azide

Draw the product of the reaction of 1-bromo-2-phenylethane with sodium azide.


(Enciphered hint 1: Bmjqibujd ovdmfpqijmjd tvctujuvujpo.)

18) Cis-1,2-Diphenyloxirane with ethoxide

Draw the three-dimensional formula of the product of the following reaction. 



(Enciphered hint 1: Usfbujoh bo fqpyjef xjui ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

19) 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.)

20) 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.)

21) Dipropyl sulfide with methyl iodide

Draw the product of the reaction of dipropyl sulfide with methyl iodide in THF.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo pddvst xjui uif tvmgjef bdujoh bt b ovdmfpqijmf.)
(Enciphered hint 2: Usjbmlzm tvmgpojvn tbmu jt cfjoh gpsnfe.)

22) Synthesis of 2-phenylethanol from oxirane

Draw the structure of an organolithium reagent giving 2-phenylethanol by reaction with oxirane, followed by addition of dilute acid.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

23) 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.)

24) 2-Bromo-1-phenylpropan-1-ol with sodium hydroxide

Draw three-dimensional formula of the product of the following reaction.



(Enciphered hint 1: Jousbnpmfdvmbs ovdmfpqijmjd tvctujuvujpo. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo.)

25) 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.)

26) Dibromoderivative with sodium cyanide

Draw the product of the following reaction.



(Enciphered hint 1: Bszm ibmjeft bsf vosfbdujwf jo ovdmfpqijmjd tvctujuvujpot.)

27) Butyl cyclopentyl ether with hydrogen bromide

Draw the organic products of the reaction of butyl cyclopentyl ether with excess hydrogen bromide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo po bo bdujwbufe (qspupobufe) fuifs.)
(Enciphered hint 2: Uif gpsnfe bmdpipmt gvsuifs sfbdu xjui uif fydftt pg izesphfo cspnjef.)

28) 2,2,3-Trimethyloxirane with sodium methoxide

Draw the product of the following reaction.



(Enciphered hint 1: Usfbujoh bo fqpyjef xjui ovdmfpqijmf mfbet up uif sjoh pqfojoh. Qbz buufoujpo up uif sfhjptfmfdujwjuz pg uif sfbdujpo.)

29) 2-Phenyloxirane with ethylamine

Draw the product of the following reaction.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)
(Enciphered hint 2: Uif ovdmfpqijmf pqfot uif pyjsbof sjoh gspn uif mftt tufsjd ijoefsfe tjuf.)

30) Ethyl methyl sulfide with propyl bromide

Draw the product of the reaction of ethyl methyl sulfide with propyl bromide in THF.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo pddvst xjui uif tvmgjef bdujoh bt b ovdmfpqijmf.)
(Enciphered hint 2: Usjbmlzm tvmgpojvn tbmu jt cfjoh gpsnfe.)

31) Propyl bromide with lithium diethyl cuprate

Draw the product of the reaction of propyl bromide with lithium diethyl cuprate in ether.



(Enciphered hint 1: Uif sfbdujpo pg bmlzm ibmjeft xjui pshbopdvqsbuft mfbe up uif gpsnbujpo pg D-D cpoe.)

32) Cyclohexyltrimethylphosphonium bromide

Draw the product of the following reaction.


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Qiptqipsvt bdut bt ovdmfpqijmf.)

33) 1-Iodopentane with sodium acetate

Draw the product of the following reaction.


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui bdfubuf bojpo bdujoh bt uif ovdmfpqijmf.)

34) Synthesis of chlorobenside

The preparation of the pesticide chlorobenside is composed of several steps. The first step is the reaction of 1-(chloromethyl)-4-nitrobenzene with 4-chloro benzenethiolate anion. Draw product of the reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo.)

Now the sulfide reacts with iron in HCl and then with NaOH.



(Enciphered hint 1: Ojusp hspvq sfevdujpo.)

35) Ethyl iodide with chiral alkoxide

Draw the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui bmlpyjef bojpo bdujoh bt uif ovdmfpqijmf.)
(Enciphered hint 2: Uif tvctujuvujpo ublft qmbdf po uif fmfduspqijmjd dbscpo bupn pg fuizm jpejef, uifsfgpsf uifsf tufsfpdifnjtusz sfnbjot vodibohfe.)

36) 2-Bromo-4-methylpentanoic acid with ammonia

Draw the product of the reaction of 2-bromo-4-methylpentanoic acid with two equivalents of ammonia. The formed compound is in its isoelectric point.



(Enciphered hint 1: B ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Uif qspevdu jt b axjuufsjpo.)

37) 1-Methyl-1,2-epoxycyclopentane with sodium methoxide

Draw three-dimensional formula of the product of the following reaction.



(Enciphered hint 1: Usfbujoh bo fqpyjef xjui ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

38) Alkylation of thiourea with 1-bromopropane

Draw thiourea and the product of its reaction with 1-bromopropane.


(Enciphered hint 1: Uijb bobmphvf pg vsfb.)


(Enciphered hint 1: Bmlzmbujpo pg uijpvsfb ublft qmbdf.)

39) 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.)

40) 1-Iodopentane with sodium cyanide

Draw the product of the reaction of 1-iodopentane with sodium cyanide.


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui dzbojef bojpo bdujoh bt uif ovdmfpqijmf.)

41) 2-Bromopentane with sodium iodide

Draw the product of the reaction of 2-bromopentane with sodium iodide in acetone.


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui jpejef bojpo bdujoh bt b ovdmfpqijmf.)

42) Synthesis of benzyl phenyl sulfide

Draw the structure of the starting compounds for the synthesis of benzyl phenyl sulfide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo qspdffejoh wjb TO2 nfdibojtn.)

43) Sulfonium salt

Draw the product of the reaction of dodecyl methyl sulfide with methyl iodide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

44) Thiophenolate with ethyliodide

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



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

45) Solvolysis of 1-bromo-1-methylcyclohexane

Draw the intermediate of solvolysis of 1-bromo-1-methylcyclohexane in methanol.


(Enciphered hint 1: Uif sfbdujpo qspdffet wjb TO1 nfdibojtn.)

46) 1-Iodobutane with sodium ethanethiolate

Draw the product of the following reaction.


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui fuibouijpmbuf bojpo bdujoh bt uif ovdmfpqijmf.)

47) 2-Bromopentane with sodium iodide

Use a three-dimensional structural formula and draw (S)-2-bromopentane and the product of its reaction with sodium iodide in acetone.

(Enciphered hint 1: Difdl dpogjhvsbujpo po tufsfphfojd dfoufs.)


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui jpejef bojpo. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo.)

48) Triphenylisopropylphosphonium bromide

Draw the product of the following reaction.


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Qiptqipsvt bdut bt ovdmfpqijmf.)

49) Bromopropane with sodium acetylide

Draw the product of sodium acetylide with 1-bromopropane.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo po bmlzm ibmjef. Bdfuzmjef jpo jt b ovdmfpqijmf.)

50) D-Mannopyranose with methanol

Draw the three-dimensional structure of the products of the reaction of beta-D-mannopyranose with methanol in the presence of acid catalyst.



(Enciphered hint 1: Uif sfbdujpo qspdffet bu uif bopnfsjd dbscpo.)

51) D-Allopyranose with methanol

Draw the three-dimensional structure of the products of the reaction of alfa-D-allopyranose with methanol in the presence of acidic catalyst.



(Enciphered hint 1: Uif sfbdujpo qspdffet bu uif bopnfsjd dbscpo pomz.)

52) 2-Bromopropanoic acid with potassium phthalimide

Draw the product of the reaction of 2-bromopropanoic acid with potassium phthalimide. The formed compound is then treated with hydrazine. Draw both products of this reaction and consider one of them being in its isoelectric point.



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


(Enciphered hint 1: Bo bnjop bdje jt sfmfbtfe cz izesbajof xijdi gpsnt b dzdmjd bdzmizesbajef.)

53) Pyridine with ethyl iodide

Draw the product of the reaction of pyridine with ethyl iodide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

54) 2-Bromohexanoic acid with sodium iodide

Draw the product of the reaction of 2-bromohexanoic acid with sodium iodide in acetone.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui jpejef bojpo bdujoh bt b ovdmfpqijmf.)

55) Malonic ester synthesis

The malonic ester synthesis is used for preparation of carboxylic acids. The starting compounds are diethyl malonate and alkyl halide. Draw the structure of alkyl bromide, which is used for the synthesis of 4-methylhexanoic acid.



(Enciphered hint 1: Ejfuizm nbmpobuf jt b tpvsdf pg uif tzouipo -DI2DPPI.)

56) 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.)

57) 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.)

58) Quinoline with methyl iodide

Draw the product of the reaction of quinoline with methyl iodide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

59) Substitution with thiolate

Draw the product of the reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

60) Oxirane with ammonia

Draw oxirane and then the product of its reaction with ammonia.


(Enciphered hint 1: Fqpyzfuibof)


(Enciphered hint 1: Usfbujoh bo fqpyjef xjui ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

61) 2-Bromopropanoic acid with ammonia

Draw the organic product of the reaction of 2-bromopropanoic acid with two equivalents of ammonia. The formed compound is in its isoelectric point.



(Enciphered hint 1: B ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Uif qspevdu jt b axjuufsjpo.)

62) 1-Methyl-1,2-epoxycyclopentane with methanol

Draw three-dimensional formula of the major product of the following reaction.



(Enciphered hint 1: Usfbujoh b qspupobufe fqpyjef xjui ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

63) Pyrrole with propyl bromide under basic conditions

Draw the products of the reaction of pyrrole with sodium hydride, the formed compound then reacts with propyl bromide:



(Enciphered hint 1: Bdje-cbtf sfbdujpo ublft qmbdf (qzsspmf jt efqspupobufe).)


(Enciphered hint 1: Uif gpsnfe O-ovdmfpqijmf sfbdut xjui bmlzm ibmjef wjb ovdmfpqijmjd tvctujuvujpo sfbdujpo.)

64) 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.)

65) 1-Bromo-3-chloropropane with sodium cyanide

Draw 1-bromo-3-chloropropane and the product of its reaction with one molar equivalent of sodium cyanide.


(Enciphered hint 1: Qspqbof xjui cspnjof boe dimp