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1) 1-Bromo-1-methylcyklohexane with sodium ethoxide

Draw 1-bromo-1-methylcyklohexane and the major product of its reaction with sodium ethoxide.

(Enciphered hint 1: F2 fmjnjobujpo. B npsf tvctujuvufe epvcmf cpoe jt gpsnfe qsfgfsbcmz.)


(Enciphered hint 1: F2 fmjnjobujpo. B npsf tvctujuvufe epvcmf cpoe jt gpsnfe qsfgfsbcmz.)

2) 1-Bromopropane with potassium tert-butoxide

Draw the product of the following reaction.


(Enciphered hint 1: F2 fmjnjobujpo pddvst.)

3) Dehydrobromination of trans-2-bromo-1-methylcyclohexane

In scheme, trans-2-bromo-1-methylcyclohexane is drawn in the conformation suitable for E2 elimination by sodium ethanolate. Write major product of this reaction.


(Enciphered hint 1: F2 fmjnjobujpo qspdffejoh wjb bouj-nfdibojtn.)

4) 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)

5) Fischer projection of 2-bromo-3-chlorobutane

Draw a three-dimensional structural formula of the given compound.


(Enciphered hint 1: Jo b Gjtdifs qspkfdujpo, bmm ipsjapoubm cpoet qspkfdu upxbset uif wjfxfs, xijmf uif wfsujdbm cpoet qspkfdu bxbz gspn uif wjfxfs.)

6) Halotane

Draw the structure of 2-bromo-2-chloro-1,1,1-trifluoroethane.


7) Halogenation of acetone

Write enol form of acetone and the product of its reaction with bromine in acetic acid.


(Enciphered hint 1: Ubvupnfsjd gpsn pg bdfupof.)


(Enciphered hint 1: Fopm gpsn pg bdfupof voefshpft uif sfbdujpo xjui fmfduspqijmjd cspnjof.)


8) 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.)

9) 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.)

10) Allyl bromide with sodium isopropoxide

Draw the product of the following reaction.



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

11) 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.)

12) Enflurane

Draw the structure of 2-chloro-1,1,2-trifluoroethyl difluoromethyl ether.


(Enciphered hint 1: Uif ovncfsjoh jo bo bmlzm tvctujuvfou tubsut po bo dbscpo bupn dpoofdufe ejsfdumz up uif nbjo dibjo.)

13) Absolute configuration of 2-bromo-3-chlorobutane

Draw the three-dimensional structural formula of (2R,3R)-2-bromo-3-chlorobutane.


(Enciphered hint 1: Qbz buufoujpo up uif sjhiu qptjujpo pg uif cpoet po tufsfpdfousft.)

14) Cyclohexanone with chlorine

Draw the product of the reaction of cyclohexanone with chlorine in an aqueous medium.



(Enciphered hint 1: Tvctujuvujpo po uif bmqib dbscpo ublft qmbdf.)

15) Absolute configuration of 1-bromo-2-chlorocyclopropane

Draw a three-dimensional structural formula of (1R,2R)-1-bromo-2-chlorocyclopropane.

(Enciphered hint 1: Qbz buufoujpo up uif sjhiu qptjujpo pg uif cpoet po tufsfpdfousft.)

16) 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.)

17) 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.)

18) Dehydrobromination of 1,2-dibromopropane

Draw the product of the reaction of 1,2-dibromopropane with sodium amide.


(Enciphered hint 1: Uxp tvddfttjwf efizespcspnjobujpot.)

19) 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.)

20) Absolute configuration of 3-iodohexane

Draw the structure of (R)-3-iodohexane.

(Enciphered hint 1: Tufsfpeftdsjqups S tqfdjgjft uif dpogjhvsbujpo po b tufsfphfojd dfousf (ifsf b dbscpo bupn cfbsjoh gpvs ejggfsfou tvctujuvfout).)

21) Dehydrobromination of 1-bromo-1,2-diphenylpropane.

Draw the product of the following reaction.


(Enciphered hint 1: Difdl dpogjhvsbujpo pg uif qspevdu - uif mfbwjoh tvctujuvfout nvtu cf bouj-qptjujpo gps uif F2 sfbdujpo.)

22) Dibromoderivative with sodium cyanide

Draw the product of the following reaction.



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

23) Propargyl chloride

Draw the structure of propargyl chloride.


(Enciphered hint 1: 3-Dimpspqspq-1-zof.)

24) Cyclohexanecarbaldehyde with bromine

Draw the product of the reaction of cyclohexanecarbaldehyde with bromine in chloroform.



(Enciphered hint 1: Tvctujuvujpo po uif bmqib dbscpo ublft qmbdf.)

25) Absolute configuration of 2,3-dibromohexane

Draw the three-dimensional structural formula of threo-2,3-dibromohexane.

(Enciphered hint 1: Tufsfp eftdsjqupst uisfp tqfdjgjft uif sfmbujwf dpogjhvsbujpo po tufsfphfojd dfousft.)
(Enciphered hint 2: Uif dpnqpvoe ibt uxp foboujpnfst.)

26) Configuration of 2,3-dibromopentane

Draw the three-dimensional structural formula of (2R,3S)-2,3-dibromopentane.


27) Halogenation of cyclopentanone

An enol form of cyclopentanone is formed in the first step of brominantion of cyclopentanone in acetic acid. Draw the formula of enol form and then the product of its bromination.

(Enciphered hint 1: Ubvupnfsjd gpsn pg dzdmpqfoubopof.)


(Enciphered hint 1: Fmfduspqijmjd gpsn pg dzdmpqfoubopof sfbdu xjui fmfduspqijmjd cspnjof.njof.)

28) Cyclohexyltrimethylphosphonium bromide

Draw the product of the following reaction.


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

29) 1-Iodopentane with sodium acetate

Draw the product of the following reaction.


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

30) Structure of a Meisenheimer complex of chloro nitro benzene with methanolate

Draw the structure of the Meisenheimer complex which is the intermediate of the following reaction.



(Enciphered hint 1: Uif sfbdujpo jt b ovdmfpqijmjd bspnbujd tvctujuvujpo qspdffejoh cz bo beejujpo-fmjnjobujpo nfdibojtn. Nfjtfoifjnfs dpnqmfy jt gpsnfe cz uif beejujpo pg b ovdmfpqijmf po uif dbscpo bupn cfbsjoh uif mfbwjoh hspvq.)

31) 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.)

32) 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.)

33) 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.)

34) 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.)

35) Dehalogenation with zinc

Draw the product of the following reaction.


(Enciphered hint 1: Efibmphfobujpo ublft qmbdf.)

36) 3-Bromopentane with sodium ethoxide

Draw the major product of the reaction of 3-bromopentane with sodium ethoxide at elevated temperature.


(Enciphered hint 1: F2 fmjnjobujpo xijdi jt gbwpvsfe jo uif sfbdujpo pg tfdpoebsz ibmphfobmlboft xjui tuspoh cbtft.)

37) 1-Chloro-4-nitrobenzene with methylamine

Draw the product of the following reaction.


(Enciphered hint 1: Ovdmfpqijmjd bspnbujd tvctujuvujpo qspdffejoh cz beejujpo-fmjnjobujpo nfdibojtn.)

38) 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.)

39) 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.)

40) 1-Iodobutane with sodium ethanethiolate

Draw the product of the following reaction.


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

41) Dehydrobromination of 2,2-dimethyl-3-bromobutane.

Draw the product of the following reaction.


(Enciphered hint 1: F2 fmjnjobujpo.)

42) 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.)

43) Triphenylisopropylphosphonium bromide

Draw the product of the following reaction.


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

44) 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.)

45) Pyridine with ethyl iodide

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



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

46) 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.)

47) Quinoline with methyl iodide

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



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

48) 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.)

49) 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 dimpsjof jo uif qptjujpot 1 boe 3.)


(Enciphered hint 1: Cspnjef bojpo jt cfuufs mfbwjoh hspvq uibo dimpsjef bojpo.)

50) Dibromoderivative with sodium cyanide 2

Draw the major product of the following reaction.



(Enciphered hint 1: Dpnqbsf uif sfbdujwjuz pg b qsjnbsz bmlzm ibmjef boe b wjozmjd ibmjef.)

51) Synthesis of benzyl bromide from ether

Draw the structure of an ether giving by the reaction with the excess of hydrogen bromide only benzyl bromide.



(Enciphered hint 1: Uif tubsujoh dpnqpvoe jt b tznnfusjdbm fuifs.)

52) Synthesis of 1,5-dibromopentane from ether

Draw the structure of an ether giving by the reaction with the excess of hydrogen bromide only 1,5-dibromopentane.



(Enciphered hint 1: Uif tubsujoh dpnqpvoe jt b dzdmjd fuifs.)

53) Hexyl chloride with alkoxide

Draw the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui bmlpyjef bojpo.)

54) 2-Bromo-2-phenylpropane with ethanol

Draw the product of the following reaction.



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

55) Pyrrolidine with allyl bromide

Draw the product of the reaction of pyrrolidine with excess allyl bromide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. B rvbufsobsz bnnpojvn tbmu jt gpsnfe.)

56) Structure to name (3)

Name the following structure:



(Enciphered hint 1: Jo obnjoh uijt dpnqpvoe, uif bmefize ibt uif ijhiftu qsjpsjuz.)

57) Structure to name (29)

Name the following structure:



(Enciphered hint 1: Ju jt b usjtvctujuvufe cfoafof.)

58) Propyl bromide with alkoxide

Draw the product of the following reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui bmlpyjef bojpo.)