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1) 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.)

2) 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.)

3) Oxidation of thiols 2

Draw the product of the reaction of cyclopentanethiol with bromine.



(Enciphered hint 1: Uif uijpm jt pyjejafe up gpsn b ejtvmgjef.)

4) 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.)

5) Oxidation of thiols 3

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



(Enciphered hint 1: Pyjebujpo pg uif uijpm pddvst bu tvmgvs bupn. Tvmgpojd bdje jt gpsnfe.)

6) Dithiol in the presence of oxygen

Draw the product of the following reaction.



(Enciphered hint 1: Uif uijpm jt pyjejafe up gpsn b ejtvmgjef.)

7) 2-Phenylethanol with TsCl

Draw 4-toluenesulfonyl chloride (tosylchloride, TsCl) and then the product of its reaction with 2-phenylethanol.


(Enciphered hint 1: Ju jt 4-nfuizmcfoafoftvmgpozm dimpsjef.)


(Enciphered hint 1: Uif sfbdujpot pg bmdpipmt xjui tvmgpozm dimpsjeft mfbe up ftufst pg tvmgpojd bdjet..)

8) Nomenclature XI

Draw the three-dimensional structural formula of (1R,2R,5S)-2-isopropyl-5-methylcyclohexane-1-thiol. 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.)

9) Nimesulide

Draw the structure of N-(4-nitro-2-phenoxyphenyl)methanesulfonamide.


(Enciphered hint 1: O-Qifozmbnjef pg nfuibof tvmgpojd bdje.)

10) 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.)

11) 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.)

12) 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.)

13) 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.)

14) 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.)

15) 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.)

16) Sulfonium salt

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



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

17) Thiophenolate with ethyliodide

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



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

18) 1-Iodobutane with sodium ethanethiolate

Draw the product of the following reaction.


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

19) Propane-1,3-dithiol in the presence of oxygen

Draw the product of the reaction of propane-1,3-dithiol in the presence of oxygen and iron(III) chloride.



(Enciphered hint 1: B ejtvmgjef jt gpsnfe.)

20) Substitution with thiolate

Draw the product of the reaction.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

21) 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.)

22) 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.)

23) 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.)

24) 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.)

25) 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.)

26) 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.)

27) Reactions of thiols 1

Draw the products (including inorganic ones) of the reaction of thiophenol with sodium hydroxide.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

28) Reaction of thiol with alkene

Thiols react in radical additions similar to hydrogen bromides. Draw the product of the reaction of butane-1-thiol with hex-1-ene using dibenzoyl peroxide as the initiator.



(Enciphered hint 1: Sbejdbm beejujpo ublft qmbdf. Sfhjptfmfdujwjuz jt esjwfo cz uif gpsnbujpo pg uif npsf tubcmf sbejdbm.)

29) Oxidation of thiols

Draw the product of the reaction of pentane-1-thiol with iodine.



(Enciphered hint 1: Uif uijpm jt pyjejafe up gpsn b ejtvmgjef.)

30) 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.)

31) Alkylation of thiols

Draw the product of the reaction of propane-1-thiol with an aqueous solution of sodium hydroxide and then the product of following reaction with 1-bromoethane.



(Enciphered hint 1: Bo bdje-cbtf sfbdujpo.)


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

32) Cyclohexanol with MsCl

Draw methanesulfonyl chloride (mesyl chloride, MsCl) and then the product of its reaction with cyclohexanol in the presence of triethylamine.


(Enciphered hint 1: Dimpsjef pg nfuiboftvmgpojd bdje.)


(Enciphered hint 1: Uif sfbdujpot pg bmdpipmt xjui tvmgpozm dimpsjeft mfbe up ftufst pg tvmgpojd bdjet.)

33) Structure to name (17)

Name the following structure:



(Enciphered hint 1: Ju jt b tvmgpojd bdje.)

34) Structure to name (14)

Name the following structure:



(Enciphered hint 1: Ju jt bo tvmgpojd bdje.)