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1) Aldolization - synthesis 1

Suggest the starting compounds for the preparation of the following product by aldol condensation.



(Enciphered hint 1: Tubsujoh dpnqpvoe dbo cf gpvoe cz jnbhjobsz ejtdpoofdujpo pg epvcmf cpoe.)

2) Triphenylmethylphosphonium-jodide

Draw triphenylphosphine and product of its reaction with methyl iodide.

(Enciphered hint 1: Qiptqibof efsjwbujwf.)


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Qiptqipsvt bupn jt ovdmfpqijmf.)

3) Preparation of ylide

Draw the product of the reaction of triphenylphosphine with ethyl bromide and the product of the successive reaction with butyllithium.



(Enciphered hint 1: Usjqifozmqiptqijof sfbdut bt ovdmfpqijmf.)


(Enciphered hint 1: Uif nptu bdjejd izesphfo jt mptu.)

4) Dieckmann condensation

Draw the products of the following reaction.



(Enciphered hint 1: Cfub-lfupftufs jt gpsnfe.)

5) Mixed claisen condensation 2

Draw the product of the mixed Claisen condensation of ethyl phenylacetate with diethyl oxalate.



(Enciphered hint 1: B cfub-lfup ftufs jt gpsnfe.)

6) Aldol condensation

Draw the final product which is formed when heating acetophenone (methyl phenyl ketone) in the presence of tert-butoxide ions in xylene at 100 °C.



(Enciphered hint 1: Bmepm dpoefotbujpo ublft qmbdf.)

7) Aldolization of propanal

Draw the structures of the intermediates and the products of the aldol reaction of propanal.



(Enciphered hint 1: Fopmbuf jt gpsnfe.)


(Enciphered hint 1: Sfbdujpo pg fopmbuf xjui bmefizef.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

8) Claisen condensation

From the following compounds choose the ones which will presumably give high yields in Claisen condensation.



(Enciphered hint 1: Uxp izesphfo bupnt bu uif bmgb-qptjujpo bsf ofddftbsz gps tnppui Dmbjtfo dpoefotbujpo.)

9) Intramolecular aldol condensation 2

Draw the products of heating of 3-methylhexane-2,5-dione in the presence of sodium hydroxide.



(Enciphered hint 1: Jousbnpmfdvmbs bmepm dpoefotbujpo ublft qmbdf. Uif dzdmf dbo cf gpsnfe wjb uxp xbzt.)

10) Aldolization - synthesis 2

Suggest the starting compounds for the preparation of the following product by aldol condensation.



(Enciphered hint 1: Tubsujoh npmfdvmft dbo cf gpvoe cz jnbhjobsz ejtdpoofujpo pg epvcmf cpoe.)

11) Mixed claisen condensation

Draw the products of Claisen condensation of ethyl benzoate with ethyl acetate.



(Enciphered hint 1: Cfub-lfup ftufs jt gpsnfe.)

12) Aldolization

Draw the structures of intermediates and products formed by aldolization of butanal.



(Enciphered hint 1: Uif sfbdujpo pg bmefizef xjui cbtf hjwft bo fopmbuf.)


(Enciphered hint 1: Uif fopmbuf pg uif gjstu bmefizef sfbdut xjui uif dbscpozm hspvq pg uif tfdpoe bmefizef.)


(Enciphered hint 1: Uif bmepm jt gpsnfe.)

13) Aldolization of aceton

Draw the product of the heating of acetone in the presence of barium hydroxide.



(Enciphered hint 1: Gpsnbujpo pg cfub-izespyzlfupof cz uif sfbdujpo pg fopmbuf xjui "ofvusbm" bdfupof.)

14) Intramolecular aldol condensation

Draw the product of heating of hexane-2,5-dione in the presence of sodium hydroxide.



(Enciphered hint 1: Jousbnpmfdvmbs bmepm dpoefotbujpo ublft qmbdf.)

15) Cyclohexyltrimethylphosphonium bromide

Draw the product of the following reaction.


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Qiptqipsvt bdut bt ovdmfpqijmf.)

16) Claisen condensation of ethyl phenylacetate

Draw the product of the Claisen condensation of ethyl phenylacetate.



(Enciphered hint 1: Cfub-lfup ftufs jt gpsnfe.)

17) Triphenylisopropylphosphonium bromide

Draw the product of the following reaction.


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo ublft qmbdf. Qiptqipsvt bdut bt ovdmfpqijmf.)

18) Aldol dehydration.

What product is formed by heating 2-ethyl-3-hydroxyhexanal?



(Enciphered hint 1: Xbufs fmjnjobujpo ublft qmbdf.)

19) Aldolization of phenylacetaldehyde

Draw the structures of the intermediates and the products of the aldol reaction of phenylacetaldehyde.



(Enciphered hint 1: Fopmbuf jt gpsnfe.)


(Enciphered hint 1: Fopmbuf sfbdut xjui uif tfdpoe bmefizef npmfdvmf.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

20) Aldolization acetone benzaldehyde

Draw the structures of the intermediates and the products of the aldol reaction of acetone with benzaldehyde catalyzed by a base (EtONa).



(Enciphered hint 1: Fopmbuf jt gpsnfe.)


(Enciphered hint 1: Fopmbuf sfbdut xjui bspnbujd bmefizef.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

21) Aldolization of cyclopentanone

Draw the structures of the intermediates and the products of the aldol reaction of cyclopentanone.



(Enciphered hint 1: Fopmbuf jt gpsnfe.)


(Enciphered hint 1: Fopmbuf sfbdut xjui lfupof.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

22) Claisen condensation of ethyl-propanoate

Draw the product of the Claisen condensation of ethyl propanoate.



(Enciphered hint 1: Cfub-lfup ftufs jt gpsnfe.)

23) Claisen condensation of ethyl acetate

Draw the products of the following reactions.



(Enciphered hint 1: Bo fopmbuf pg cfub-lfupftufs jt gpsnfe.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo. B cfub-lfupftufs jt gpsnfe.)

24) Claisen condensation - cyclohexanone

Draw the products of mixed Claisen condensation of cyclohexanone with ethyl formate followed by acidification.



(Enciphered hint 1: Fopmbuf pg cfub-lfupbmefizef jt gpsnfe.)


(Enciphered hint 1: Bdje-cbtf frvjmjcsjvn.)