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1) 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.)

2) Allyl bromide with sodium isopropoxide

Draw the product of the following reaction.



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

3) 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.)

4) Acid mediated ether cleavage

Draw the structure of oxonium ion that is an intermediate in the acid-catalysed cleavage of ethers.



(Enciphered hint 1: Fuifs bdut bt b cbtf.)

5) 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.)

6) 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.)

7) 1-Bromobutan-2-ol with sodium hydroxide

Draw the product of the following reaction.



(Enciphered hint 1: Jousbnpmfdvmbs ovdmfpqijmjd tvctujuvujpo.)

8) 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.)

9) 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.)

10) 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.)

11) 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.)

12) Boiling points of ethers

Select an ether with the lowest boiling point.



(Enciphered hint 1: Dpotjefs cpjmjoh qpjout bobmphpvtmz up uif dpssftqpoejoh izespdbscpot.)

13) 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.)

14) 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.)

15) 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.)

16) 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.)

17) 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.)

18) Structure to name (4)

Name the following structure:



(Enciphered hint 1: Ju jt bo fuifs.)

19) 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.)

20) Methyl phenyl sulfide with sodium periodate

Draw the product of the reaction of methyl phenyl sulfide with sodium periodate in water.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Qfsjpebuf pyjebuft tvmgjeft up tvmgpyjeft pomz.)

21) 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.)

22) 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.)

23) Sulfonium salt

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



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

24) 1-Iodobutane with sodium ethanethiolate

Draw the product of the following reaction.


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

25) 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.)

26) 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.)

27) 4-Tert-butylthiane with sodium periodate

Oxidation of 4-tert-butylthiane with sodium periodate gives a mixture of two compounds. Draw their structure.



(Enciphered hint 1: Ejbtufsfpjtpnfst bsf gpsnfe.)

28) Structure to name (5)

Name the following structure:



(Enciphered hint 1: Ju jt bo bmlpyzbmdpipm.)

29) Anisole with hydrogen bromide

Draw the organic products of the reaction of methyl phenyl ether with the excess of hydrogen bromide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo po bo bdujwbufe (qspupobufe) fuifs.)
(Enciphered hint 2: Uif sfbdujpo pomz qspdffet po uif dbscpo bupn xjiu tq3-izcsjejabujpo. )

30) Dibutyl ether with hydrogen bromide

Draw the product of the reaction of dibutyl ether with the excess of hydrogen bromide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo po bo bdujwbufe (qspupobufe) fuifs.)
(Enciphered hint 2: Uif gpsnfe cvubopm sfbdut gvsuifs voefs uif sfbdujpo dpoejujpot.)

31) Tetrahydrofuran with hydrogen iodide

Draw the product of the reaction of tetrahydrofuran with the excess of hydrogen iodide.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo po bo bdujwbufe (qspupobufe) fuifs.)
(Enciphered hint 2: Uif gpsnfe jpepqfoubopm gvsuifs sfbdut xjui uif fydftt pg izesphfo jpejef.)

32) 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.)

33) 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.)

34) Methyl phenyl sulfide with hydrogen peroxide

Draw the product of the reaction of methyl phenyl sulfide with the excess of hydrogen peroxide in acetic acid.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Uif fydftt pg izesphfo qfspyjef pyjeft tvmgjeft up tvmgpoft.)

35) 1-Chloro-1,2-diphenylpropane with sodium methanethiolate

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.)

36) Hexyl chloride with alkoxide

Draw the product of the following reaction.



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

37) 2-Bromo-2-phenylpropane with ethanol

Draw the product of the following reaction.



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

38) Tert-butyl methyl ether with hydrogen iodide

Draw the products of the reaction of tert-butyl methyl ether with the excess of hydrogen iodide.



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

39) Butyl propyl sulfide with sodium periodate

Draw the product of the reaction of butyl propyl sulfide with sodium periodate in water.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Qfsjpebuf pyjejaft tvmgjeft up tvmgpyjeft pomz.)

40) Butyl propyl sulfide with hydrogen peroxide

Draw the product of the reaction of butyl propyl sulfide with the excess of hydrogen peroxide in acetic acid.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Uif fydftt pg izesphfo qfspyjef pyjejaft tvmgjeft up tvmgpoft.)

41) Dipropyl sulfide with peracetic acid

Draw the product of the reaction of dipropyl sulfide with the excess of peracetic acid.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)
(Enciphered hint 2: Uif fydftt pg qfsbdfujd bdje pyjejaft tvmgjeft up tvmgpoft.)

42) But-1-ene with peracetic acid

Draw the product of the following reaction.



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

43) Cyclohexene with trifluoroacetic peracid

Draw the product of the following reaction.



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

44) 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.)

45) (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.)

46) (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.)

47) (R)-2-Ethyloxirane with NaOH

Draw (R)-2-ethyloxirane and then draw the three-dimensional formula of the product of its reaction with NaOH. 


(Enciphered hint 1: Dbscpo D2 jt dijsbm.)


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

48) Trans-2,3-diethyloxirane with NaOH

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



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

49) Synthesis of sulfides

Organic sulfides can be prepared by alkylation of sodium salt of a sulfide with alkyl iodide. Draw the starting compounds for methyl phenyl sulfide synthesis.



(Enciphered hint 1: Bmlzmbujpo pg cfoafofuijpmbuf jt uif pomz xbz.)

50) Propyl bromide with alkoxide

Draw the product of the following reaction.



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

51) Formal charge (2)

Write the formal charge of the highlighted oxygen atom. Use one of these examples ( 0, -1, +1, -2, +2, etc.) for your answer.



(Enciphered hint 1: Gpsnbm dibshf = (ovncfs pg pvufs-tifmm fmfduspot jo gsff bupn) - (ovncfs pg pvufs-tifmm fmfduspot jo cpoefe bupn))

52) Oxidation number (4)

Write the oxidation number of the carbon atom C1 in 1,1-dimethoxyethane. Use one of these examples ( 0, -1, +1, -2, +2, etc.) for your answer.



(Enciphered hint 1: Gps qvsqptft pg dpnqvujoh pyjebujpo tubuft, fmfduspot jo b cpoe cfuxffo bupnt pg ejggfsfou fmfnfout cfmpoh up uif npsf fmfduspofhbujwf bupn; fmfduspot jo b cpoe cfuxffo bupnt pg uif tbnf fmfnfou bsf opu dpnqvufe. (gpsnbm py. ovncfs = ovncfs pg npsf fmfduspofhbujwf cpoefe bupnt - ovncfs pg mftt fmfduspofhbujwf cpoefe bupnt (f.h. izesphfot)))
(Enciphered hint 2: Dpotjefs izesphfo bupn bu D1.)