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1) Strength of acids 5

Choose the most acidic and the least acidic compound.



The most acidic phenol.


(Enciphered hint 1: Bdjejuz jt jodsfbtfe xjui uif qsftfodf boe uif ovncfs pg fmfduspo-xjuiesbxjoh hspvqt.)

The least acidic phenol.


(Enciphered hint 1: Dpotjefs fmfduspojd fggfdu pg uif tvctujuvfout.)

2) Keto and enol forms 3

Draw the keto and enol forms of 2,4-pentanedione.


(Enciphered hint 1: Ubvupnfst.)

3) Allyl carbocation 3

Draw the resonance structure of the following carbocation.



(Enciphered hint 1: Sftpobodf tusvduvsf jt dsfbufe cz npwjoh qj fmfduspot ps gsff fmfduspo qbjs upxbset uif qptjujwf dibshf.)

4) Strength of acids 4

Choose the most acidic and the least acidic compound.



The most acidic compound.


(Enciphered hint 1: Dpotjefs bdjejuz pg wbsjpvt dmbtt pg dpnqpvoet.)

The least acidic compound.


(Enciphered hint 1: Dpotjefs bdjejuz pg wbsjpvt dmbtt pg dpnqpvoet.)

5) Enolates 1

Describe the mechanism of the reaction of acetone with hydroxide ion in an aqueous medium and the formation of enolate.



(Enciphered hint 1: Bdje-cbtf frvjmmjcsjvn.)


(Enciphered hint 1: Sftpobodf tusvduvsf.)

6) Aromaticity (1)

From the following compounds choose those that are aromatic.



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

7) Boiling points of ethers

Select an ether with the lowest boiling point.



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

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) Keto and enol form 1

Draw the keto and enol forms of acetone.


(Enciphered hint 1: Ubvupnfst.)

11) Structure of L-proline

Draw the structure of L-proline ((S)-pyrrolidine-2-carboxylic acid) under strongly acidic conditions, under strongly basic conditions and in its isoelectric point.


L-proline under strongly acidic conditions:


(Enciphered hint 1: Dpotjefs qspupobujpo pg bmm cbtjd hspvqt.)

L-proline under strongly basic conditions:


(Enciphered hint 1: Dpotjefs efqspupobujpo pg bmm bdjejd hspvqt.)

L-proline in its isoelectric point:


(Enciphered hint 1: [xjuufsjpo.)

12) Structure of D-Ala-D-Phe

Draw the structure of dipeptide D-Ala-D-Phe in its isoelectric point.


(Enciphered hint 1: E-Bmb jt (S)-2-bnjopqspqbopjd bdje. E-Qif nfbot (S)-2-bnjop-3-qifozmqspqbopjd bdje.)

13) Allyl carbocation 1

Draw the resonance structure of the following carbocation.



(Enciphered hint 1: Sftpobodf tusvduvsf jt gpsnfe cz npwjoh qj fmfduspot ps gsff fmfduspo qbjs upxbset uif qptjujwf dibshf.)

14) 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).)

15) Allyl carbocation 2

Draw the resonance structure of the following carbocation.



(Enciphered hint 1: Sftpobodf tusvduvsf jt dsfbufe cz npwjoh qj fmfduspot ps gsff fmfduspo qbjs upxbset uif qptjujwf dibshf.)

16) Keto and enol form 2

Draw the keto and enol forms of cyclopentanone.


(Enciphered hint 1: Ubvupnfst.)

17) Stable radical 2

Draw the structure of the most stable radical with the molecular formula C7H7.


(Enciphered hint 1: B cfoazm-uzqf sbejdbm.)

18) Strength of acids 2

Choose the most acidic compound.



(Enciphered hint 1: Bdjejuz jodsfbtft xjui uif qsftfodf boe uif ovncfs pg fmfduspo-xjuiesbxjoh hspvqt.)

19) Structure of L-alanine

Draw the structure of L-alanine ((S)-2-aminopropanoic acid) under strongly acidic conditions, under strongly basic conditions and in its isoelectric point.


L-alanine under strongly acidic conditions:


(Enciphered hint 1: Dpotjefs qspupobujpo pg bmm cbtjd hspvqt.)

L-alanine under strongly basic conditions:


(Enciphered hint 1: Dpotjefs efqspupobujpo pg bmm bdjejd hspvqt.)

L-alanine in its isoelectric point:


(Enciphered hint 1: [xjuufsjpo.)

20) Strength of acids 1

Choose the most acidic and the least acidic compound.



The most acidic compound.


(Enciphered hint 1: Dpotjefs fmfduspojd fggfdu pg tvctujuvfout.)

The least acidic compound.


(Enciphered hint 1: Dpotjefs fmfduspojd fggfdu pg tvctujuvfout.)

21) Reactivity in nucleophilic acyl substitution

All of the following acetic acid derivatives react with ammonia upon formation of acetamide. Choose the most reactive one.



(Enciphered hint 1: Uif sfbdujwjuz jt jodsfbtfe cz uif qsftfodf pg bo fmfduspo-xjuiesbxjoh hspvq jo uif npmfdvmf.)

22) Order of basicity 1

Choose the most basic and the least basic structure from the given compounds.



The most basic compound.


(Enciphered hint 1: Uif cbtjdjuz efqfoet po uif fmfduspojd fggfdut pg uif tvctujuvfout.)

The least basic compound.


(Enciphered hint 1: Uif cbtjdjuz efqfoet po uif fmfduspojd fggfdut pg uif tvctujuvfout.)

23) Order of basicity 2

Choose the most basic and the least basic structure from the given compounds.



The most basic compound.


(Enciphered hint 1: Uif cbtjdjuz efqfoet po uif fmfduspojd fggfdut pg uif tvctujuvfout.)

The least basic compound.


(Enciphered hint 1: Uif cbtjdjuz efqfoet po uif fmfduspojd fggfdut pg uif tvctujuvfout.)

24) Alkanes C6H14

Draw all alkanes that have the molecular formula C6H14. Do not consider stereoisomers.


(Enciphered hint 1: Uifsf bsf gjwf dpotujuvujpobm jtpnfst. )

25) Reactions of thiols 1

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



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

26) Structure of L-phenylalanine

Draw the structure of L-phenylalanine ((S)-2-amino-3-phenylpropanoic acid) under strongly acidic conditions, under strongly basic conditions and in its isoelectric point.


L-phenylalanine under acidic conditions:


(Enciphered hint 1: Dpotjefs qspupobujpo pg cbtjd hspvqt.)

L-phenylalanine under basic conditions:


(Enciphered hint 1: Dpotjefs efqspupobujpo pg bdjejd hspvqt.)

L-phenylalanine in its isoelectric point:


(Enciphered hint 1: [xjuufsjpo.)

27) Strength of acids 3

Choose the most acidic and the least acidic compound.



The least acidic compound.


(Enciphered hint 1: Bdjejuz jt jodsfbtfe cz uif qsftfodf boe uif ovncfs pg fmfduspo xjuiesbxjoh hspvqt.)

The most acidic compound.


(Enciphered hint 1: Bdjejuz jt jodsfbtfe cz uif qsftfodf boe uif ovncfs pg fmfduspo xjuiesbxjoh hspvqt.)

28) Cycloalkanes C5H10

Draw all compounds that have the molecular formula C5H10 and contain a ring in their structure. Do not consider stereoisomers.


(Enciphered hint 1: Uifsf bsf gjwf dpotujuvujpobm jtpnfst.)