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1) 1-Bromo-1-methylcyklohexane with sodium ethoxide

Draw 1-bromo-1-methylcyklohexane and the major product of its reaction with sodium ethoxide.

(Enciphered hint 1: F2 fmjnjobujpo. B npsf tvctujuvufe epvcmf cpoe jt gpsnfe qsfgfsbcmz.)


(Enciphered hint 1: F2 fmjnjobujpo. B npsf tvctujuvufe epvcmf cpoe jt gpsnfe qsfgfsbcmz.)

2) 1-Bromopropane with potassium tert-butoxide

Draw the product of the following reaction.


(Enciphered hint 1: F2 fmjnjobujpo pddvst.)

3) Dehydrobromination of trans-2-bromo-1-methylcyclohexane

In scheme, trans-2-bromo-1-methylcyclohexane is drawn in the conformation suitable for E2 elimination by sodium ethanolate. Write major product of this reaction.


(Enciphered hint 1: F2 fmjnjobujpo qspdffejoh wjb bouj-nfdibojtn.)

4) 2-Bromopentane with sodium ethoxide

Draw all possible products of the reaction of 2-bromopentane with sodium ethoxide. Consider both substitution and elimination.


(Enciphered hint 1: Cpui tvctujuvujpo boe fmjnjobujpo qspdffe bt dpnqfujujwf sfbdujpot.)

5) Dehydrobromination of 1,2-dibromopropane

Draw the product of the reaction of 1,2-dibromopropane with sodium amide.


(Enciphered hint 1: Uxp tvddfttjwf efizespcspnjobujpot.)

6) Dehydrobromination of 1-bromo-1,2-diphenylpropane.

Draw the product of the following reaction.


(Enciphered hint 1: Difdl dpogjhvsbujpo pg uif qspevdu - uif mfbwjoh tvctujuvfout nvtu cf bouj-qptjujpo gps uif F2 sfbdujpo.)

7) 1-Methylcyclopentanol with sulfuric acid

Draw all the organic products of the reaction of 1-methylcyclopentanol with sulfuric acid.



(Enciphered hint 1: Ufsujbsz bmdpipmt jo bdjejd nfejb sfbejmz gpsn dbscpdbujpot. Uif dbscpdbujpo uifo fmjnjobuft b qspupo. Uxp qspevdut dbo cf gpsnfe.)

8) Carbocation rearrangement during dehydration

During the following reaction, the initially formed carbocation undergoes a rearrangement. Draw the structures of the starting and rearranged carbocations.



(Enciphered hint 1: Qspupobujpo jt gpmmpxfe cz xbufs fmjnjobujpo.)


(Enciphered hint 1: Uif esjwjoh gpsdf pg uif sfbssbohfnfou jt uif gpsnbujpo pg npsf tubcmf dbscpdbujpo.)

9) Cope elimination

Draw the products of the thermal cleavage of the following N-oxide.



(Enciphered hint 1: Fmjnjobujpo ublft qmbdf. Bo bmlfof jt gpsnfe.)

10) Butane-1,2,4-triol with p-toluenesulfonic acid

Draw the product of the reaction of (S)-butane-1,2,4-triol with catalytic amount of p-toluenesulfonic acid.



(Enciphered hint 1: Bo jousbnpmfdvmbs sfbdujpo ublft qmbdf.)

11) Dehydration of 1-methylcyclohexanol (mechanism)

Fill in the intermediates and products in the dehydration of 1-methylcyclohexanol by the action of sulfuric acid.



(Enciphered hint 1: Qspupobujpo pg uif izespyz hspvq tubsut uif nfdibojtn.)


(Enciphered hint 1: Uif dbscpdbujpo jt gpsnfe cz mptt pg xbufs.)


(Enciphered hint 1: Npsf tubcmf bmlfof jt uif nbkps qspevdu pg uif sfbdujpo.)

12) Dehalogenation with zinc

Draw the product of the following reaction.


(Enciphered hint 1: Efibmphfobujpo ublft qmbdf.)

13) 3-Bromopentane with sodium ethoxide

Draw the major product of the reaction of 3-bromopentane with sodium ethoxide at elevated temperature.


(Enciphered hint 1: F2 fmjnjobujpo xijdi jt gbwpvsfe jo uif sfbdujpo pg tfdpoebsz ibmphfobmlboft xjui tuspoh cbtft.)

14) Dehydrobromination of 2,2-dimethyl-3-bromobutane.

Draw the product of the following reaction.


(Enciphered hint 1: F2 fmjnjobujpo.)

15) Hofmann elimination

Draw the major product of the following reaction.



(Enciphered hint 1: Mftt-tvctujuvufe bmlfof jt gpsnfe.)

16) Reactions of amides

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



(Enciphered hint 1: Efizesbujpo ublft qmbdf.)

17) Cleavage of an acetate

Draw the major product of the thermal cleavage of the following acetate.



(Enciphered hint 1: Bdfubuf dmfbwbhf. Ju jt tzo- cfub-fmjnjobujpo pg bdfujd bdje.)

18) Cleavage of acetate 2

Draw the major product of the thermal cleavage of the following acetate.



(Enciphered hint 1: Tzo-cfub-fmjnjobujpo pg bdfujd bdje.)

19) 1-Methylcyclohexanol with sulfuric acid

Draw 1-methylcyclohexanol and then the major product of its reaction with sulfuric acid.


(Enciphered hint 1: Ufsujbsz bmdpipm.)


(Enciphered hint 1: Ufsujbsz bmdpipmt jo bdjejd nfejb sfbejmz gpsn dbscpdbujpot xijdi uifo fmjnjobuf b qspupo. Uif nbkps qspevdu jt gpsnfe bddpsejoh up uif [bjutfw't svmf.)

20) Butan-2-ol with H3PO4

Draw all organic products of the following reaction.



(Enciphered hint 1: Ufsujbsz boe tfdpoebsz bmdpipmt jo bdjejd nfejb gpsn dbscpdbujpot sfbejmz. Uif dbscpdbujpo uifo fmjnjobuft b qspupo. Uif nbkps qspevdu jt gpsnfe bddpsejoh up uif [bjutfw't svmf. Dpotjefs tufsfpjtpnfst.)

21) Pinacol rearrangement 1 - mechanism

During pinacol (2,3-dimethylbutane-2,3-diol) dehydration 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.)

22) 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.)