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1) Cyclohexene with carbene

Draw the product of the following reaction.



(Enciphered hint 1: Dbscfof jt hfofsbufe boe uifo ju jt beefe up b epvcmf cpoe.)

2) 4-Methylpent-3-en-2-on with nucleophile

Draw the product of the reaction of 4-methylpent-3-en-2-on with thiophenol in presence of base.



(Enciphered hint 1: 1,4-beejujpo.)

3) Oxirane with methylmagnesium iodide

Draw the product of the following reaction.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

4) Butylmagnesium bromide with acetone

Draw the product of the reaction of butylmagnesium bromide with acetone and subsequent acidification.



(Enciphered hint 1: Uif gjstu sfbdujpo jt beejujpo pg b Hsjhobse sfbhfou up b dbscpozm hspvq.)


(Enciphered hint 1: Uif sfbdujpo pg uif bmlpyjef xjui ejmvuf bdje jt bo bdje-cbtf sfbdujpo.)

5) 1-Bromobutane with magnesium

Draw the product of the following reaction.



(Enciphered hint 1: Vtf b dpwbmfou cpoe up esbx b dbscpo-nfubm cpoe .)

6) Butylmagnesium bromide with ethanol

Draw the products of the reaction of butylmagnesium bromide with ethanol.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

7) Pentylmagnesium chloride with silicon(IV) chloride

Draw the product of the following reaction.



(Enciphered hint 1: Usbotnfubmmbujpo sfbdujpo ublft qmbdf.)

8) But-3-en-2-on with nucleophile

Draw the product of the reaction of but-3-en-2-on with lithium diethyl cuprate, followed by addition of water.



(Enciphered hint 1: 1,4-Beejujpo pg ovdmfpqijmf up bo bmgb, cfub-votbuvsbufe tztufn ublft qmbdf.)

9) Isopropylmagnesium bromide with CO2

Draw the product of the reaction of isopropylmagnesium bromide with carbon dioxide and subsequent acidification.



(Enciphered hint 1: Beejujpo pg uif Hsjhobse sfbhfou up uif dbscpo ejpyjef.)


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

10) Butylmagnesium bromide with water

Draw the organic product of the reaction of butylmagnesium bromide with water.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

11) Phenylmagnesium bromide with butanal

Draw the product of the reaction of phenylmagnesium bromide with butanal and subsequent acidification.



(Enciphered hint 1: Uif gjstu sfbdujpo jt beejujpo pg b Hsjhobse sfbhfou up b dbscpozm hspvq. )


(Enciphered hint 1: Uif sfbdujpo pg uif bmlpyjef xjui ejmvuf bdje jt bo bdje-cbtf sfbdujpo.)

12) Butylmagnesium chloride with cadmium(II) chloride

Draw the product of the following reaction.



(Enciphered hint 1: Vtf b dpwbmfou cpoe up esbx b dbscpo-nfubm cpoe .)

13) 2-Phenyloxirane with methylmagnesium bromide

Draw the product of the following reaction.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

14) Hex-2-enal with nucleophile

Draw the product of the reaction of hex-2-enal with ethylmagnesium bromide, followed by addition of water.



(Enciphered hint 1: 1,2-Beejujpo pg uif ovdmfpqijmf up uif dbscpozm hspvq ublft qmbdf.)

15) Cis-1,2-Diphenyloxirane with ethoxide

Draw the three-dimensional formula of the product of the following reaction. 



(Enciphered hint 1: Usfbujoh bo fqpyjef xjui ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

16) Ethyl cyclopentanecarboxylate with EtMgBr

Draw the product of the reaction of ethyl cyclopentanecarboxylate with ethylmagnesium bromide.



(Enciphered hint 1: Uxp npmft pg uif pshbopnfubmmjd sfbhfou sfbdu xjui pof npmf pg ftufs. Uif gjstu frvjwbmfou pg uif sfbhfou gpsnt b lfupof, xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou.)

17) Synthesis of 2-phenylethanol from oxirane

Draw the structure of an organolithium reagent giving 2-phenylethanol by reaction with oxirane, followed by addition of dilute acid.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

18) But-3-en-2-on with nucleophile

Draw the product of the reaction of but-3-en-2-on with ethyllithium.



(Enciphered hint 1: 1,2-beejujpo qsfepnjobuft.)

19) Hex-2-enal with nucleophile

Draw the product of the reaction of hex-2-enal with methyllithium.



(Enciphered hint 1: 1,2-beejujpo ublft qmbdf.)

20) 2-Phenyloxirane with ethylamine

Draw the product of the following reaction.



(Enciphered hint 1: Usfbunfou pg bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)
(Enciphered hint 2: Uif ovdmfpqijmf pqfot uif pyjsbof sjoh gspn uif mftt tufsjd ijoefsfe tjuf.)

21) Acyl chloride with methyllithium

Draw the product of the following reaction.



(Enciphered hint 1: Uxp npmft pg uif pshbopnfubmmjd sfbhfou sfbdu xjui pof npmf pg bdzm dimpsjef. Uif gjstu frvjwbmfou pg uif sfbhfou gpsnt b lfupof, xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou.)

22) 4-Methylpent-3-en-2-one with nucleophile

Draw the product of the reaction of 4-methylpent-3-en-2-one with methylmagnesium bromide.



(Enciphered hint 1: 1,2-Beejujpo pg uif ovdmfpqijmf ublft qmbdf.)

23) Butylmagnesium bromide with but-1-yne

Draw the products of the reaction of butylmagnesium bromide with but-1-yne.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

24) Phenyllithium with deuterium oxide

Draw phenyllithium and the product of its reaction with deuterium oxide.


(Enciphered hint 1: Ju jt bo pshbopnfubmmjd dpnqpvoe dpoubjojoh D-Mj cpoe.)



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

25) Diisopropylamine with butyllithium

Draw the products of the reaction of diisopropylamine with butyllithium.



(Enciphered hint 1: B tbmu boe bo bmlbof bsf gpsnfe.)

26) Propyl bromide with lithium diethyl cuprate

Draw the product of the reaction of propyl bromide with lithium diethyl cuprate in ether.



(Enciphered hint 1: Uif sfbdujpo pg bmlzm ibmjeft xjui pshbopdvqsbuft mfbe up uif gpsnbujpo pg D-D cpoe.)

27) 1-Phenylprop-2-en-1-on with butyllithium

Does the reaction of 1-phenylprop-2-en-1-on with butyllithium proceed as 1,2- or 1,4-addition? Draw the product of the reaction after aqueous work-up.



(Enciphered hint 1: Qspevdu pg 1,2-beejujpo qsfepnjobuft.)

28) Pentano-5-lactone with methyllithium

Draw the product of the following reaction of pentano-5-lactone.



(Enciphered hint 1: Ftufst xjui bmlzmmjuijvn sfbdu xjui 1:2 tupjdijpnfusz.)

29) Bromobenzene with cuprate

Draw the product of the following reaction:



(Enciphered hint 1: Jo uif sfbdujpo pg pshbopdvqsbuft xjui bszm cspnjeft, pof bszm hspvq pg uif pshbopdvqsbuf tvctujuvuft uif ibmphfo bupn jo uif bszm cspnjef boe b ofx D-D cpoe jt gpsnfe.)

30) Butylmagnesium bromide with ethanal

Draw the product of the reaction of butylmagnesium bromide with ethanal and subsequent acidification.



(Enciphered hint 1: Uif gjstu sfbdujpo jt beejujpo pg b Hsjhobse sfbhfou up b dbscpozm hspvq. )


(Enciphered hint 1: Uif sfbdujpo pg uif bmlpyjef xjui ejmvuf bdje jt bo bdje-cbtf sfbdujpo.)

31) Phenylmagnesium bromide with 1-phenylpropan-2-one

Draw the product of the reaction of phenylmagnesium bromide with 1-phenylpropan-2-one and subsequent acidification.



(Enciphered hint 1: Uif gjstu sfbdujpo jt beejujpo pg b Hsjhobse sfbhfou up b dbscpozm hspvq.)


(Enciphered hint 1: Uif sfbdujpo pg uif bmlpyjef xjui ejmvuf bdje jt bo bdje-cbtf sfbdujpo.)

32) 1-Bromobutane with lithium

Draw the product of the following reaction.



(Enciphered hint 1: Vtf b dpwbmfou cpoe up esbx b dbscpo-nfubm cpoe .)

33) Ethyl propanoate with CH3MgBr

Draw the product of the reaction of ethyl propanoate with two molar equivalents of methylmagnesium bromide (after acidification).



(Enciphered hint 1: Uxp npmft pg Hsjhobse sfbhfou sfbdu xjui pof npmf pg ftufs. Uif gjstu frvjwbmfou pg uif sfbhfou gpsnt b lfupof, xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou. Uif mbtu tufq - sfbdujpo pg uif bmlpyjef xjui xbufs - jt bo bdje-cbtf sfbdujpo.)

34) Preparation of pentan-1-ol from organometallic compound

Draw the requiered carbonyl compound of the following reaction:



(Enciphered hint 1: Dpnqbsf ovncfs pg dbscpo bupnt jo uif tubsujoh nbufsjbm boe jo uif qspevdu.)

35) Chlorobenzene with lithium dibutyl cuprate

Draw the product of the reaction of chlorobenzene with lithium dibutyl cuprate.



(Enciphered hint 1: Uif sfbdujpo pg bszm ibmjeft xjui pshbopdvqsbuft mfbe up uif gpsnbujpo pg D-D cpoe.)

36) Synthesis of n-alkyl arene (2)

One method to synthesize n-alkyl arenes uses organocuprates where the organometallic compound reacts with aryl halide and a new C-C bond is formed. Draw the product of the following reaction:



(Enciphered hint 1: Jo uif sfbdujpo pg pshbopdvqsbuft xjui bszm cspnjeft, pof bmlzm hspvq pg uif pshbopdvqsbuf tvctujuvuft uif ibmphfo bupn jo uif bszm cspnjef boe b ofx D-D cpoe jt gpsnfe.)

37) (Z)-Hex-3-ene with carbene

Draw the three-dimensional formulae of product(s) of the following reaction. 



(Enciphered hint 1: Tzo beejujpo pg dbscfof.)

38) Benzonitrile with butylmagnesium bromide

First draw the product of the reaction between benzonitrile and butylmagnesium bromide in diethyl ether and then the product after acidic hydrolysis.



(Enciphered hint 1: Uif tupjdijpnfusz pg uif sfbdujpo jt 1:1.)


(Enciphered hint 1: Izespmztjt bggpset b dbscpozm dpnqpvoe.)

39) Acetonitrile with butylmagnesium chloride

First draw the product of the reaction between acetonitrile and butylmagnesium chloride in diethyl ether and then the product after acidic hydrolysis.



(Enciphered hint 1: Uif tupjdijpnfusz pg uif sfbdujpo jt 1:1.)


(Enciphered hint 1: B dbscpozm dpnqpvoe jt gpsnfe.)

40) N-Methylaniline with ethyllithium

Draw all of the products of the reaction of N-methylaniline with ethyllithium.



(Enciphered hint 1: B tbmu boe bo bmlbof bsf gpsnfe.)

41) Synthesis of n-alkyl arene (3)

One method to synthesize n-alkyl arenes uses organocuprates whre the organometallic compound reacts with aryl halide and a new C-C bond is formed. Draw the product of the following reaction:



(Enciphered hint 1: Jo uif sfbdujpo pg pshbopdvqsbuft xjui bszm jpejeft, pof bmlzm hspvq pg uif pshbopdvqsbuf tvctujuvuft uif ibmphfo bupn jo uif bszm jpejef boe b ofx D-D cpoe jt gpsnfe.)

42) Trans-2,3-diethyloxirane with NaOH

Draw the three-dimensional formula of the product of the following reaction. 



(Enciphered hint 1: Usfbujoh bo fqpyjef xjui b ovdmfpqijmf mfbet up uif sjoh pqfojoh.)

43) Phenylmagnesium chloride with ethyl formate

Draw the product of the reaction of phenylmagnesium chloride with ethyl formate and subsequent acidification.



(Enciphered hint 1: Uxp npmft pg Hsjhobse sfbhfou sfbdu xjui pof npmf pg ftufs. Uif gjstu frvjwbmfou pg Hsjhobse sfbhfou bggpset b lfupof xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou pg uif Hsjhobse sfbhfou.)


(Enciphered hint 1: Uif gjobm tufq, uif sfbdujpo pg uif bmlpyjef xjui ejmvuf bdje, jt bo bdje-cbtf sfbdujpo.)

44) Phenylmagnesium bromide with ethyl acetate

Draw the product of the reaction of phenylmagnesium bromide with ethyl acetate and subsequent acidification.



(Enciphered hint 1: Uxp npmft pg Hsjhobse sfbhfou sfbdu xjui pof npmf pg ftufs. Uif gjstu frvjwbmfou pg Hsjhobse sfbhfou bggpset b lfupof xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou pg uif Hsjhobse sfbhfou. )


(Enciphered hint 1: Uif sfbdujpo pg uif bmlpyjef xjui ejmvuf bdje, jt bo bdje-cbtf sfbdujpo.)

45) (Z)-Pent-2-ene with carbene

Draw the three-dimensional formulae of products of the following reaction. 



(Enciphered hint 1: Sbdfnbuf jt gpsnfe.)

46) Ethyl benzoate with phenyllithium

Draw the product of the reaction of ethyl benzoate with phenyllithium.



(Enciphered hint 1: Uxp npmft pg uif pshbopnfubmmjd sfbhfou sfbdu xjui pof npmf pg ftufs. Uif gjstu frvjwbmfou pg uif sfbhfou gpsnt b lfupof, xijdi uifo sfbdut xjui uif tfdpoe frvjwbmfou.)

47) Acetyl chloride with Et2CuLi

Draw the product of the reaction of acetyl chloride with lithium diethylcuprate.



(Enciphered hint 1: Ovdmfpqijmjd bdzm tvctujuvujpo. Uif qspevdu jt b lfupof.)

48) 4-Methylpent-3-en-2-one with nucleophile

Draw the product of the reaction of 4-methylpent-3-en-2-one with lithium divinylcuprate, followed by addition of water.



(Enciphered hint 1: 1,4-Beejujpo pg ovdmfpqijmf up bo bmgb, cfub-votbuvsbufe tztufn ublft qmbdf.)

49) Structure to name (31)

Name the following structure:



(Enciphered hint 1: Ju jt bo bszmmjuijvn.)

50) Structure to name (32)

Name the following structure:



(Enciphered hint 1: Ju jt bo bmlzmmjuijvn)

51) Structure to name (33)

Name the following structure:



(Enciphered hint 1: Ju jt bo bmlzmnbhoftjvn jpejef)

52) Structure to name (34)

Name the following structure:



(Enciphered hint 1: Ju jt bo pshbopdvqsbuf.)