Print questions | Press CTRL-P to print

1) Pyrrolidine with HNO2

Draw the product of the reaction of pyrrolidine with sodium nitrite in the presence of hydrochloric acid.



(Enciphered hint 1: O-Ojusptbujpo ublft qmbdf.)

2) Furan with pyridine sulfur trioxide complex

Draw furan and the product of its monosulfonation.


(Enciphered hint 1: Gjwf-nfncfsfe pyzhfo dpoubjojoh ifufspbspnbujd dpnqpvoe.)


(Enciphered hint 1: Fmfduspqijmjd tvctujuvujpo. Uif sfhjptfmfdujwjuz fotvft gspn uif gpsnbujpo pg b tubcjmjafe dbscpdbujpo evsjoh uif sfbdujpo xjui bo fmfduspqijmf.)
(Enciphered hint 2: D-T cpoe jt gpsnfe cz tvmgpozmbujpo.)

3) Pyrrole with acetyl nitrate

Draw the product of the reaction of pyrrole with acetyl nitrate.



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

4) 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.)

5) Thiophene with sulfuric acid

Draw thiophene and the product of its reaction with concentrated sulfuric acid.


(Enciphered hint 1: Uijpqifof jt b gjwf-nfncfsfe bspnbujd ifufspdzdmjd dpnqpvoe dpoubjojoh pof tvmgvs bupn.)


(Enciphered hint 1: Npop-tvmgpobujpo pddvst.)

6) Nomenclature VII

Draw the structure of methyl-3-aminopyrazine-2-carboxylate.


(Enciphered hint 1: Ftufs pg dbscpyzmjd bdje. Qzsbajof jt ifufspdzdmjd bspnbujd dpnqpvoe.)

7) Nifedipine

Draw the structure of dimethyl-1,4-dihydro-2,6-dimethyl-4-(2-nitrophenyl)pyridine-3,5-dicarboxylate.


(Enciphered hint 1: Ejftufs pg ejdbscpyzmjd bdje.)

8) Aromaticity (2)

From the following compounds choose those do not behave as aromatic compounds.



(Enciphered hint 1: Qmbobs tuvduvsft xjui 4o+2 qj-fmfduspot (Iv̈dlfm't svmf). Uif svmf xbt psjhjobmz efgjofe gps npopdzdmjd dpnqpvoet. Ofwfsuifmftt uifsf bsf npsf dpnqmfy tusvduvsft xijdi cfibwf mjlf bspnbujdt.)

9) Order of basicity (3)

Choose the least basic heterocyclic compound.



(Enciphered hint 1: Uif cbtjdjuz jt jogmvfodfe cz dpokvhbujpo pg uif mpof fmfduspo qbjs joup uif bspnbujd tztufn.)

10) Pyridine with bromine

Draw pyridine and the product of its monobromination.


(Enciphered hint 1: Qzsjejof jt b tjy-nfncfsfe ifufspbspnbujd dpnqpvoe dpoubjojoh b ojusphfo bupn.)


(Enciphered hint 1: Fmfduspqijmjd tvctujuvujpo. Uif tvctujuvfou jt ejsfdufe up qptjujpo 3 pg uif qzsjejof sjoh.)

11) Thiophene with acetyl chloride

Draw the product of the reaction of thiophene with acetyl chloride in the presence of aluminium trichloride.



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo ublft qmbdf. Ublf dbssf bcpvu sfhjptfmfdujwjuz.)

12) 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.)

13) Thiophene with peroxybenzoic acid

Draw the product of the reaction of thiophene with peroxybenzoic acid.



(Enciphered hint 1: Pyjebujpo bu tvmgvs pddvst.)

14) Quinoline with HNO3/H2SO4

Draw the products of the reaction of quinoline with the mixture of nitric acid and sulfuric acid.



(Enciphered hint 1: Ojusbujpo ublft qmbdf po npsf bdujwbufe sjoh.)

15) Pyridine-3-carboxaldehyde with 2,4-dinitrophenylhydrazine

Draw the product of the reaction of pyridine-3-carboxaldehyde with 2,4-dinitrophenylhydrazine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf.)

16) Quinoline with bromine

Draw the products of the reaction of quinoline with bromine in sulfuric acid in the presence of silver sulfate.



(Enciphered hint 1: Uif fmfduspqijmjd bspnbujd tvctujuvujpo pg npsf sfbdujwf sjoh ublft qmbdf.)
(Enciphered hint 2: Uxp qspevdut pg uif sfbdujpo bsf gpsnfe.)

17) Pyrrole - electrophilic substitution

Draw three resonance structures which support the hypothesis of electrophilic bromination proceeding at position two of the pyrrole ring.



(Enciphered hint 1: Uif dbujpo gpsnfe dbo cf ejtqmbzfe vtjoh uisff sftpobodf gpsnt.)

18) 4-Methylpyridine with NBS

Draw the product of the reactions of 4-methylpyridine with N-bromosuccinimide under radical conditions.



(Enciphered hint 1: Uif sfbdujpo ublft qmbdf jo uif tjef dibjo pg uif bspnbujd sjoh.)

19) Furan with maleic anhydride

Draw the product of the following reaction.



(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

20) 4-Methylpyridine with KMnO4

Draw the products of the reaction of 4-methylpyridine with potassium permanganate.



(Enciphered hint 1: Pyjebujpo pg uif nfuizm hspvq ublft qmbdf.)

21) Aromaticity 3

From the following compounds choose those which behave as aromatic compounds.



(Enciphered hint 1: Qmbobs tztufnt xjui 4o+2 dpokvhbufe qj-fmfduspot (Iv̈dlfm't svmf).)

22) Furan with hydrogen

Draw the product of the reaction of furan with hydrogen using Ni as a catalyst: 



(Enciphered hint 1: Izesphfobujpo pg bspnbujd dpnqpvoe ublft qmbdf. )

23) Pyridine with hydrogen peroxide

Draw the product of the reaction of pyridine with hydrogen peroxide in acetic acid:



(Enciphered hint 1: Qzsjejof bt puifs ufsujbsz bnjoft jt pyjejafe up O-pyjef.)

24) Pyridine and pyridine N-oxide under nitration

Draw the products of the reactions of pyridine and pyridine N-oxide under nitration conditions:



(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo up uif qptjujpo 3 ublft qmbdf.)


(Enciphered hint 1: Ojusbujpo pg qzsjejof O-pyjef ublft qmbdf bu uif qptjujpo 4.)

25) Pyridine with ethyl iodide

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



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

26) Dioxane dibromide

Bromination reactions of furan and pyrrole require mild reaction conditions; therefore dioxane dibromide is used as a bromination reagent. Draw its structure.


(Enciphered hint 1: Ju jt uif beevdu gpsnfe gspn uif Mfxjt cbtf ejpybof boe uif Mfxjt bdje cspnjof.)

27) Acetyl nitrate

Nitration reactions of furan and pyrrole need mild conditions with acetyl nitrate as a reagent. Draw the structure of acetyl nitrate.


(Enciphered hint 1: Ju jt uif njyfe boizesjef pg ojusjd boe bdfujd bdjet)

28) Pyridine sulfur trioxide complex

Sulfonation reactions of furan and pyrrole require mild reaction conditions; therefore, pyridine sulfur trioxide complex is used as a reagent. Draw its structure.


(Enciphered hint 1: Ju jt uif beevdu gpsnfe gspn uif Mfxjt cbtf qzsjejof boe uif Mfxjt bdje tvmgvs usjpyjef.)

29) 1,2,5-Trimethylpyrrole

Draw the structure of 1,2,5-trimethylpyrrole.


(Enciphered hint 1: Qzsspmf jt b gjwf-nfncfsfe ojusphfo-dpoubjojoh ifufspbspnbujd dpnqpvoe.)

30) Pyridine with HNO3/H2SO4

Draw pyridine and the product of its mononitration.


(Enciphered hint 1: B tjy-nfncfsfe ifufspbspnbujd dpnqpvoe xjui b ojusphfo bupn.)


(Enciphered hint 1: Fmfduspqijmjd bspnbujd tvctujuvujpo up qptjujpo 3.)

31) Quinoline with methyl iodide

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



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf.)

32) Nomenclature II

Draw the structure of 4,5-bis(bromomethyl)-3-hydroxy-2-methylpyridine.


(Enciphered hint 1: Qzsjejof jt b ifufspdzdmjd dpnqpvoe dpotjtujoh pg b tjy-nfncfsfe bspnbujd sjoh.)

33) 2-Methylthiophene

Draw the structure of 2-methylthiophene.


(Enciphered hint 1: Uijpqifof jt b tvmgvs bupn-dpoubjojoh gjwf-nfncfsfe ifufspbspnbujd dpnqpvoe. Ifufspdzdmft bsf ovncfsfe tubsujoh gspn ifufspbupn.)

34) 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.)

35) Reactions of amides

What product is formed by the reaction of pyridine-3-carboxamide with phosphorus(V) oxide?



(Enciphered hint 1: Efizesbujpo ublft qmbdf.)

36) 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.)

37) Furan with acetylenedicarboxylate

Draw the product of the following reaction.



(Enciphered hint 1: Ejfmt-Bmefs sfbdujpo.)

38) Synthesis of pyridine-4-carboxylic acid

Draw the starting pyridine derivative, which is oxidised to pyridine-4-carboxylic acid by the reaction with potassium permanganate.



(Enciphered hint 1: Uifsf jt op dibohf pg dbscpo bupnt ovncfs.)

39) Furan with dioxan dibromide

Draw the structure of the product of the reaction of furan with dioxane dibromide.



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

40) 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.)

41) Indole with dioxane dibromide

Draw the product of the reaction of indole with dioxane dibromide.



(Enciphered hint 1: Fmfduspqijmjd tvctujuvujpo.)

42) Nomenclature IV

Draw the structure of 2-[(dimethylamino)methyl]furan.


(Enciphered hint 1: Gvsbo jt b ifufspdzdmjd dpnqpvoe dpotjtujoh pg b gjwf-nfncfsfe bspnbujd sjoh.)