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1) Benzaldehyde with peracid

Benzaldehyde can be used to synthesize phenol. Fill in the following schemes:



(Enciphered hint 1: Cbfzfs-Wjmmjhfs pyjebujpo.)


(Enciphered hint 1: Izespmztjt pg bo ftufs.)

2) Diphenylketone and Beckmann rearangement

Diphenylketone reacts with hydroxylamine and the formed compound is treated under acid-catalyzed conditions. Draw the products of both reactions.



(Enciphered hint 1: Beejujpo pg izespyzmbnjof up dbscpozm hspvq.)



(Enciphered hint 1: Cfdlnboo sfbssbohfnfou. Bnjef jt gpsnfe.)

3) Butanamide with bromine

Draw the carbon-containing products of the reaction of butanamide with bromine in the presence of sodium hydroxide.



(Enciphered hint 1: Ipgnboo sfbssbohfnfou.)

4) Pentan-3-one and Beckmann rearangement

Pentan-3-one reacts with hydroxylamine and the formed compound is treated under acid-catalyzed conditions. Draw the products of both reactions.



(Enciphered hint 1: Izespyzmbnjof beejujpo up dbscpozm hspvq.)



(Enciphered hint 1: Cfdlnboo sfbssbohfnfou. Bnjef jt gpsnfe.)

5) Aryl ester with aluminium(III) chloride

Draw the product of heating of phenyl propanoate with aluminium(III) chloride:



(Enciphered hint 1: Gsjft sfbssbohfnfou.)

6) Hoffmann rearrangement

Draw all the carbon-containing products of the Hoffmann rearrangement of phenylacetamide.



(Enciphered hint 1: Bo bnjef jt dpowfsufe joup b qsjnbsz bnjof.)

7) Cyclohexanone and Beckmann rearangement

Cyclohexanone reacts with hydroxylamine and the formed compound is treated under acid-catalyzed conditions. Draw the products of both reactions.



(Enciphered hint 1: Ovdmfpqijmjd beejujpo pg izespyzmbnjof up dbscpozm hspvq.)



(Enciphered hint 1: Cfdlnboo sfbssbohfnfou. Dzdmjd bnjef (mbdubn) jt gpsnfe.)

8) Curtius rearrangement

Draw all the products (including inorganic) of the Curtius rearrangement of benzoyl azide.



(Enciphered hint 1: Qsjnbsz bnjoft bsf gpsnfe cz Dvsujvt sfbssbohfnfou pg bdzm bajeft.)

9) Hofmann rearrangement - mechanism

Draw the structure of the isocyanate, that is the key intermediate in the Hofmann rearrangement of pentanamide.



(Enciphered hint 1: Bo bmlzm buubdife up uif dbscpozm hspvq njhsbuft up ojusphfo.)

10) Pinacol rearrangement 3 - mechanism

During dehydration of the vicinal diol shown below a carbocation is formed, which undergoes rearrangement. Draw the structure of the carbocation thus formed.



(Enciphered hint 1: B npsf tubcmf dbscpdbujpo jt gpsnfe wjb bmlzm sfbssbohfnfou. )

11) Hydrogen chloride addition with rearrangement (1)

Addition of hydrogen chloride to 3-methylbut-1-ene gives, because of rearrangement of carbocationic intermediate, a mixture of isomeric chlorides. Draw structure of carbocations and final chlorides



(Enciphered hint 1: Dbscpdbujpo gpsnfe cz qspupo beejujpo up b epvcmf cpoe voefshpft sfbssbohfnfou cz nfuizm tijgu.)


(Enciphered hint 1: Cpui dbscpdbujpot sfbdu xjui dimpsjef jpo.)

12) Pinacol rearrangement 2 - mechanism

During dehydration of 1,2-dimethylcyclohexane-1,2-diol a carbocation is formed, which undergoes rearrangement. This rearrangement yields two carbocations. Draw their structure.



(Enciphered hint 1: Uxp ejggfsfou bmlzm hspvqt dbo sfbssbohf.)

13) Hydrogen chloride addition with rearrangement

Addition of hydrogen chloride to 3,3-dimethylbut-1-ene gives, because of rearrangement of carbocationic intermediate, a mixture of isomeric chlorides. Draw structure of carbocations and final chlorides



(Enciphered hint 1: Dbscpdbujpo gpsnfe cz qspupo beejujpo up b epvcmf cpoe voefshpft sfbssbohfnfou cz nfuizm tijgu.)


(Enciphered hint 1: Cpui dbscpdbujpot sfbdu xjui dimpsjef jpo.)

14) Dehydration of alcohol

Draw the structure of compound A from the following reaction series.



(Enciphered hint 1: Jo efizesbujpo, uif sfbssbohnfou mfbejoh up uif npsf tubcmf cfoazmjd dbscpdbujpo ublft qmbdf.)