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1) 1-Chloro-4-(trifluoromethyl)benzene with sodium methoxide

What product is formed by the reaction of 1-chloro-4-(trifluoromethyl)benzene with sodium methoxide in methanol?



(Enciphered hint 1: Usjgmvpspnfuizm hspvq bmmpxt ovdmfpqijmjd bspnbujd tvctujuvujpo up qspdffe tjnjmbsmz bt b ojusp hspvq.)

2) 2,4,6-Trinitrochlorobenzene with hydroxide

Draw the product of the reaction of 2,4,6-trinitrochlorobenzene with hydroxide anion.



(Enciphered hint 1: Ovdmfpqijmjd bspnbujd tvctujuvujpo.)

3) Benzyne - Diels-Alder reaction

When furan is added to the mixture of bromobenzene and potassium amide, benzyne  intermediate is trapped by furane under formation 4+2 cycloadduct. Draw structures of benzyne and 4+2 cycloadduct.



(Enciphered hint 1: Bu gjstu, fmjnjobujpo ublft qmbdf.)


(Enciphered hint 1: Gvsbo tfswft bt b usbq up dbquvsf uif joufsnfejbuf - cfoazof. Gvsbo jt b ejfof, cfoazof jt b ejfopqijmf.)

4) 2,6-Dideuteriochlorobenzene with sodium amide

What products are formed by the reaction of 2,6-dideuteriochlorobenzene with sodium amide in ammonia. First, draw the reactive intermediate and then product(s) of the reaction.



(Enciphered hint 1: Fmjnjobujpo ublft qmbdf bggpsejoh bszof.)


(Enciphered hint 1: Uxp qspevdut bsf gpsnfe cz sfbdujpo pg opo-tznnfusjdbm bszof xjui b ovdmfpqijmf.)

5) Dichlorobenzene with nitric acid and then with ammonia

What product is formed by the reaction of 1,3-dichlorobenzene with a mixture of nitric and sulfuric acids (consider the major product), and then with ammonia in ethylene glycol?



(Enciphered hint 1: Bmtp tufsjd ijoesbodf qmbzt spmf evsjoh fmfdupqijmjd tvctujuvujpo.)


(Enciphered hint 1: B njyuvsf pg uxp qspevdut jt gpsnfe.)

6) 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.)

7) Rate of nucleophilic substitution

From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C.



(Enciphered hint 1: B ojusp hspvq gbdjmjubuft ovdmfpqijmjd bspnbujd tvctujuvujpo pomz jo qptjujpot psuip boe qbsb.)

8) Nucleophilic substitution rate in halonitrobenzenes

From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C.



(Enciphered hint 1: Uif sfbdujwjuz pg ibmpcfoafoft jo ovdmfpqijmjd bspnbujd tvctujuvujpo efdsfbtft jo psefs G>Dm>Cs.)

9) 2-Chloropyridine with amide

Draw the products (both organic and inorganic) of the reaction of 2-chloropyridine with amide anion.



(Enciphered hint 1: Ovdmfpqijmjd bspnbujd tvctujuvujpo ublft qmbdf.)

10) p-Bromotoluene with sodium hydroxide

A mixture of two products is formed by the reaction of p-bromotoluene with sodium hydroxide. Draw the unstable intermediate and then the final products.



(Enciphered hint 1: Uif sfbdujpo qspdffet wjb fmjnjobujpo-beejujpo nfdibojtnt xjui bo bszof cfjoh bo joufsnfejbuf.)


(Enciphered hint 1: Uif sfbdujpo pg opo-tznnfusjdbm bszof xjui b ovdmfpqijmf bggpset uxp qspevdut.)

11) Chloronitrobenzene with thiolate

What product is formed by the reaction of 1-chloro-4-methyl-2-nitrobenzene with potassium benzylthiolate?



(Enciphered hint 1: Bspnbujd ovdmfpqijmjd tvctujuvujpo qspdffejoh cz beejujpo-fmjnjobujpo nfdibojtn.)

12) Rate of nucleophilic substitution in halonitrobenzenes.

From the following two compounds choose the one which will react faster with sodium methoxide in methanol at 50 °C.



(Enciphered hint 1: B ojusp hspvq gbdjmjubuft ovdmfpqijmjd bspnbujd tvctujuvujpo jo psuip boe qbsb qptjujpo.)

13) Mechanism of nucleophilic substitution of 2-chloropyridine

Draw the structure of the intermediate which is formed by the attack of 2-chloropyridine with amide anion. 



(Enciphered hint 1: Uif sfbdujpo qspdffet wjb beejujpo-fmjnjobujpo nfdibojtn.)

14) Reaction of benzenesulfonic acid

Draw the product of the reaction of benzenesulfonic acid with sodium hydroxide at 300 °C.



(Enciphered hint 1: Uif sfqmbdfnfou pg uif -TP3I hspvq ublft qmbdf.)

15) Val-Phe-Gly with 1-fluoro-2,4-dinitrobenzene

Draw tripeptide Val-Phe-Gly and treat it with 1-fluoro-2,4-dinitrobenzene (Sanger's reagent). The formed compound is then hydrolyzed under acidic conditions. Draw the formed compounds.


(Enciphered hint 1: Wbm = wbmjof, Qif = qifozmbmbojof, Hmz = hmzdjof.)


(Enciphered hint 1: Bspnbujd ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Tbohfs't sfbhfou pomz sfbdut xjui gsff bnjop hspvq.)


(Enciphered hint 1: Qfqujef cpoet bsf dmfbwfe.)

16) 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.)

17) Chloronitrobenzenes - reaction with nucleophiles

From the following structures choose the ones which can undergo a substitution of chlorine atom with hydroxide anion.



(Enciphered hint 1: Ojusp hspvq qspwjeft ovdmfpqijmjd bspnbujd tvctujuvujpo cz sftpobodf fggfdu xijdi jt opu qpttjcmf jo b nfub qptjujpo.)

18) 1-Chloroanthraquinone with methoxide anion

1-Chloroanthraquinone reacts with methoxide anion. Draw the structure of a Meisenheimer complex and the final product.



(Enciphered hint 1: Nfjtfoifjnfs dpnqmfy jt gpsnfe cz beejujpo pg b ovdmfpqijmf boe ju jt tubcjmjafe cz sftpobodf.)

(Enciphered hint 1: Bspnbujd ovdmfpqijmjd tvctujuvujpo.)

19) Chlorobenzene - aromatic substitution

Chlorobenzene usually does not react with nucleophiles. However, at high temperatures and high pressure phenol is formed by the reaction with water. Reaction takes place by an elimination-addition mechanism. First, draw the product of elimination and then the product of the addition of water to the unstable intermediate.



(Enciphered hint 1: Cfoazof jt gpsnfe.)


(Enciphered hint 1: Qspevdu jt gpsnfe cz beejujpo pg b ovdmfpqijmf up cfoazof.)

20) 1-Chloro-4-nitrobenzene with methylamine

Draw the product of the following reaction.


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

21) Dichloro-nitrobenzene with hydroxide

Draw the product of the reaction of 1,2-dichloro-4-nitrobenzene with hydroxide anion.



(Enciphered hint 1: Ojusp hspvq qspwjeft ovdmfpqijmjd bspnbujd tvctujuvujpo cz sftpobodf fggfdu xijdi jogmvfodft uif sfbdujwjuz pomz jo psuip ps qbsb qptjujpo.)

22) Nitrochlorobenzenes - charge stabilization

Show by means of resonance structures the stabilization of intermediate anion in the substitution of 2-nitrochlorobenzene with hydroxide anion.



(Enciphered hint 1: Sfbdujpo ublft qmbdf cz beejujpo-fmjnjobujpo nfdibojtn.)

23) m-Bromotoluene with sodium hydroxide

A mixture of three products is formed during the reaction of m-bromotoluene with NaOH. Draw the unstable intermediates and the final products.



(Enciphered hint 1: Uxp jtpnfsjd joufsnfejbuft bsf gpsnfe cz fmjnjobujpo tufq.)


(Enciphered hint 1: Beejujpo pg xbufs bggpset 3 jtpnfsjd qspevdut.)

24) Chlorodinitrobenzene with hydrazine

What product is formed by the reaction of 2,4-dinitrochlorobenzene with hydrazine in triethylene glycol?



(Enciphered hint 1: Bspnbujd ovdmfpqijmjd tvctujuvujpo qspdffejoh cz beejujpo-fmjnjobujpo nfdibojtn.)

25) Phe-Leu with 1-fluoro-2,4-dinitrobenzene

Draw dipeptide Phe-Leu and treat it with 1-fluoro-2,4-dinitrobenzene (Sanger's reagent). The formed compound is then hydrolyzed under acidic conditions. Draw the formed compounds.


(Enciphered hint 1: Qif = qifozmbmbojof, Mfv = mfvdjof.)


(Enciphered hint 1: Bspnbujd ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Tbohfs't sfbhfou pomz sfbdut xjui gsff bnjop hspvq. )


(Enciphered hint 1: B qfqujef cpoe jt dmfbwfe.)

26) 14C bromobenzene with amide

Draw the intermediate and then all products of the reaction of bromobenzene with potassium amide. The bromobenzene is labeled by a radioactive isotope 14C.



(Enciphered hint 1: Sfbdujpo ublft qmbdf cz fmjnjobujpo-beejujpo nfdibojtn.Cfoazof jt bo joufsnfejbuf.)


(Enciphered hint 1: Uxp qspevdut bsf gpsnfe cz uif sfbdujpo pg cfoazof xjui b ovdmfpqijmf.)

27) 4-Chloropyridine with sodium ethoxide

Draw the product of the reaction of 4-chloropyridine with sodium ethoxide.



(Enciphered hint 1: Ovdmfpqijmjd bspnbujd tvctujuvujpo ublft qmbdf.)