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1) Nitrile with LiAlH4

Draw the product of the reaction of 2-phenylacetonitrile with lithium aluminium hydride.



(Enciphered hint 1: Sfevdujpo pg uif dzbop hspvq ublft qmbdf.)

2) Butanal with NaBH4

Draw the product of the reaction of butanal with sodium borohydride followed by the reaction with water.



(Enciphered hint 1: Sfevdujpo pg uif pyp hspvq gpmmpxfe cz bo bdje-cbtf sfbdujpo pg uif gpsnfe bmlpyjef xjui xbufs.)

3) Reduction of benzene

A radical anion is formed as an intermediate in the reaction of benzene with sodium in liquid ammonia and methanol. It is then protonized. Draw the structure of the radical anion and then of the radical intermediates.



(Enciphered hint 1: Sbejdbm boe fmfduspo qbjs bsf mpdbmjafe jo uif qptjujpot 1 boe 4.)


(Enciphered hint 1: Qspupobujpo cz nfuibopm.)

4) Reduction of (E)-oct-2-en-4-yne

Draw the product of the reaction of (E)-oct-2-en-4-yne with hydrogen using the Lindlar catalyst. Consider the configuration of the product.



(Enciphered hint 1: Dpotjefs difnptfmfdujwjuz pg izesphfobujpo xjui uif Mjoembs dbubmztu.)

5) Reduction of L-glucononitrile

Draw the three-dimensional structure of the open-chain form of the product of the following reaction of L-glucononitrile.



(Enciphered hint 1: Sfevdujpo pg ojusjm up jnjof gpmmpxfe cz izespmztjt mfbejoh up bmefizef ublft qmbdf.)

6) Lactam with LiAlD4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo cz efvufsjef jpo ublft qmbdf.)

7) Nitrobenzene, substitution and reduction

Draw the product of nitrobenzene chlorination followed by hydrogenation on palladium.



(Enciphered hint 1: Fmfduspqijmjd tvctujuvujpo. Sfhjptfmfdujwjuz jt dpouspmmfe cz tvctujuvfou bmsfbez qsftfou po cfoafof sjoh.)


(Enciphered hint 1: Dbubmzujd izesphfobujpo.)

8) 1-Bromobutane with magnesium

Draw the product of the following reaction.



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

9) Pentylmagnesium chloride with silicon(IV) chloride

Draw the product of the following reaction.



(Enciphered hint 1: Usbotnfubmmbujpo sfbdujpo ublft qmbdf.)

10) Reductive amination 4

Draw the starting compounds which produce the tertiary amine shown bellow on reductive amination.



(Enciphered hint 1: B dbscpozm dpnqpvoe boe bo bnjof bsf offefe.)

11) Hydrogenation of but-1-yne

Draw the product of hydrogenation of but-1-yne on a Lindlar catalyst.



(Enciphered hint 1: Beejujpo pg izesphfo up b usjqmf cpoe. Uif sfbdujpo qspevdu jt bo bmlfof, xijdi jt opu gvsuifs izesphfobufe po b Mjoembs dbubmztu.)

12) Anisole with sodium

Anisole (methyl phenyl ether) undergoes Birch reduction by sodium in liquid ammonia. Draw the product of the reaction.



(Enciphered hint 1: Uxp-fmfduspo sfevdujpo pg bspnbujd sjoh.)
(Enciphered hint 2: Tvctujuvfout xjui N+ mfbe up uif qspevdut xjui uif nptu ijhimz tvctujuvufe epvcmf cpoet, j.f. uif hspvq jt po uif epvcmf cpoe.)


13) Butanal with hydrogen

Draw the product of the reaction of butanal with hydrogen catalyzed by nickel.



(Enciphered hint 1: Dbubmzujd izesphfobujpo.)

14) Methyl phenyl ketone with NaBH4

Draw the product of the reaction of methyl phenyl ketone with sodium borohydride followed by the reaction with water.



(Enciphered hint 1: Sfevdujpo pg uif dbscpozm hspvq gpmmpxfe cz bdje-cbtf sfbdujpo pg uif gpsnfe bmlpyjef xjui xbufs.)

15) 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 .)

16) Nitrile with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo pg cpui gvodujpobm hspvqt ublft qmbdf.)

17) D-Mannose with NaBH4

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



(Enciphered hint 1: Sfevdujpo pg uif dbscpozm hspvq ublft qmbdf.)

18) Benzaldehyde with KOH

Benzaldehyde reacts with KOH. Draw the organic products of the reaction after its acidic work-up.



(Enciphered hint 1: Dboojaabsp sfbdujpo ublft qmbdf xifo bmefizeft xjuipvu bmgb izesphfo bsf usfbufe voefs cbtjd dpoejujpot.)

19) Amide with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

20) Pentano-5-lactone with LiAlD4

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



(Enciphered hint 1: Sfevdujpo cz efvufsjef jpo ublft qmbdf.)

21) Pentano-5-lactone with DIBAH

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



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

22) Butyronitrile with lithium aluminium hydride

Draw the product of the reaction of butyronitrile with lithium aluminium hydride.



(Enciphered hint 1: Sfevdujpo pg uif ojusjmf ublft qmbdf.)

23) Benzoic acid with sodium

Benzoic acid undergoes Birch reduction by sodium in liquid ammonia. Draw the product of the reaction.



(Enciphered hint 1: Uxp-fmfduspo sfevdujpo pg bspnbujd sjoh.)
(Enciphered hint 2: Tvctujuvfout xjui N- mfbe up uif qspevdut ibwjoh uif tvctujuvfou dpoofdufe up uif dbscpo bupn xjui tq3 izcsjejabujpo.)


24) Hydrogenation of cyclohexene

Draw the product of the following reaction.


(Enciphered hint 1: Beejujpo pg izesphfo up b epvcmf cpoe.)

25) Methyl phenyl ketone with zinc amalgam

Draw the product of the reaction of methyl phenyl ketone with zinc amalgam in the presence of hydrochloric acid.



(Enciphered hint 1: Sfevdujpo pg uif dbscpozm hspvq.)

26) 2,2,2-Triphenylacetaldehyde with NaOH

2,2,2-Triphenylacetaldehyde reacts with NaOH. Draw the organic products of the reaction after its acidic work-up.



(Enciphered hint 1: Dboojaabsp sfbdujpo ublft qmbdf xifo bmefizeft xjuipvu bmgb izesphfo bsf usfbufe voefs cbtjd dpoejujpot.)

27) Reductive amination 2

Draw the product of the reaction of cyclohexanone with ethylamine in the presence of sodium cyanoborohydride.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up bo jnjof, xijdi jt uifo sfevdfe cz uif bdujpo pg tpejvn dzbopcpspizesjef.)

28) Cyclopropanecarboxylic acid with LiAlD4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo gpmmpxfe cz bdje-cbtf sfbdujpo pg uif bmlpyjef xjui xbufs.)

29) Butan-1-ol with sodium

Draw the products of the reaction of butan-1-ol with sodium. Use the first box for the organic and the second box for the inorganic product.



(Enciphered hint 1: Tbmu efsjwfe gspn bmdpipm jt gpsnfe evsjoh uif sfbdujpo.)

(Enciphered hint 1: Npmfdvmbs izesphfo jt gpsnfe evsjoh uif sfbdujpo.)

30) 5-Oxohexanoic acid with NaBH4

Draw the product of the reaction of 5-oxohexanoic acid with sodium borohydride.



(Enciphered hint 1: Pyp hspvq jt sfevdfe boe bgufs xpsl-vq cz xbufs, uif qspevdu dzdmjaft.)

31) Hydrogenation of 1,2-dimethylcyclohexene

Draw the product of the following reaction. Show the relative configuration of the product.


(Enciphered hint 1: Djt-beejujpo pg izesphfo up b epvcmf cpoe.)

32) Ethyl propanoate with LiAlH4

Draw the organic products of the following reaction.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

33) Azide with LiAlH4

Draw the product of the reaction of 3-phenylpropyl azide with lithium aluminium hydride.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

34) Reduction of but-2-yne

Draw the product of the reaction of but-2-yne with sodium in liquid ammonia. Consider the stereochemistry of the reaction.



(Enciphered hint 1: Sfevdujpo pg bo bmlzof cz tpejvn. Uif sfbdujpo jt tufsfptfmfdujwf, mfbejoh up usbot-bmlfof bt uif nbkps qspevdu.)

35) Acetone with magnesium

A radical anion is formed by the reaction of acetone with magnesium. Draw the structure of the radical anion.



(Enciphered hint 1: Tjohmf-fmfduspo sfevdujpo pg bdfupof.)

Draw the product of the coupling reaction between two radical anions followed by the reaction with water.


(Enciphered hint 1: Qjobdpm dpvqmjoh sfbdujpo.)

36) D-Glucose with NaBH4

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



(Enciphered hint 1: Sfevdujpo pg uif dbscpozm hspvq ublft qmbdf. B ofx dijsbm dfoufs jt opu gpsnfe evsjoh uif sfbdujpo.)

37) Reduction of hex-1-en-4-yne

Draw the product of the reaction of hex-1-en-4-yne with hydrogen with Lindlar catalyst. Consider the configuration of the product.



(Enciphered hint 1: Dpotjefs difnp- boe tufsfp-tfmfdujwjuz pg izesphfobujpo xjui uif Mjoembs dbubmztu.)

38) Propanoic acid with LiAlH4

Draw the product of the reaction of propanoic acid with lithium aluminum hydride.



(Enciphered hint 1: Sfevdujpo gpmmpxfe cz bdje-cbtf sfbdujpo pg uif bmlpyjef xjui xbufs. Pof frvjwbmfou pg izesjef jt vtfe up gpsn tbmu pg dbscpyzmjd bdje xijdi jt uifo sfevdfe.)

39) Furan with hydrogen

Draw the product of the reaction of furan with hydrogen using Ni as a catalyst: 



(Enciphered hint 1: Izesphfobujpo pg bspnbujd dpnqpvoe ublft qmbdf. )

40) 1-Bromobutane with lithium

Draw the product of the following reaction.



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

41) Lactam with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujpo ublft qmbdf.)

42) Ethyl 2-phenylacetate with DIBAH

Draw the product of the following reaction of ethyl 2-phenylacetate.



(Enciphered hint 1: Difnptfmfdujwf sfevdujpo ublft qmbdf.)

43) Diester with LiAlH4

Draw the product of the following reaction.



(Enciphered hint 1: Cpui ftufs gvodujpobm hspvqt sfbdu.)

44) 1-Tert-butyl-4-nitrobenzene with hydrogen

Draw the product of the reaction of 1-tert-butyl-4-nitrobenzene with hydrogen on a platinum catalyst.



(Enciphered hint 1: Uif ojusp hspvq jt sfevdfe.)

45) Reductive amination

The reaction of butanal with aniline in the presence of sodium cyanoborohydride leads first to an imine, which is subsequently reduced. First draw the structure of the imine.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up bo jnjof.)

Next, draw the structure of the final product obtained by the reduction of the imine with sodium cyanoborohydride.


(Enciphered hint 1: Sfevdujpo pg uif D=O epvcmf cpoe ublft qmbdf.)

46) Acetophenone with hydrazine

Draw the product of the reaction of acetophenone with hydrazine and the product of its subsequent heating with potassium hydroxide.



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


(Enciphered hint 1: Xpmgg-Ljtiofs sfevdujpo.)

47) Pyruvic acid with NH3/NaBH4

Draw the product of the following reaction.



(Enciphered hint 1: Sfevdujwf bnjobujpo pg dbscpozm hspvq.)

48) Hydrogenation of but-1-yne (2)

Draw the product of of hydrogenation of but-1-yne on a platinum catalyst.



(Enciphered hint 1: Beejujpo pg izesphfo po b usjqmf cpoe.)

49) Hydrogenation of but-2-yne

Draw the product of hydrogenation of but-2-yne on a Lindlar catalyst. Consider the stereochemistry of the reaction.



(Enciphered hint 1: Djt-beejujpo pg izesphfo up b usjqmf cpoe bggpsejoh bo bmlfof. Uif bmlfof jt opu gvsuifs izesphfobufe po uif Mjoembs dbubmztu.)

50) Reduction of hept-3-yne

Draw the product of the reaction of hept-3-yne with sodium in liquid ammonia. Consider the stereochemistry of the reaction.



(Enciphered hint 1: Sfevdujpo pg bo bmlzof cz tpejvn. Uif sfbdujpo jt tufsfptfmfdujwf, mfbejoh up usbot-bmlfof bt uif nbkps qspevdu.)

51) Hydrogenation of hept-3-yne

Draw the product of hydrogenation of hept-3-yne on a Lindlar catalyst.



(Enciphered hint 1: Beejujpo pg izesphfo up b usjqmf cpoe. Uif sfbdujpo qspevdu jt bo bmlfof, xijdi jt opu gvsuifs izesphfobufe po b Mjoembs dbubmztu. Qbz buufoujpo po tufsfpdifnjtusz.)

52) Reductive amination 3

Draw the product of the reaction of benzaldehyde with dibutylamine in the presence of sodium cyanoborohydride.



(Enciphered hint 1: Beejujpo pg O-ovdmfpqijmf up uif dbscpozm hspvq mfbet up bo jnjojvn tbmu, xijdi jt uifo sfevdfe cz uif bdujpo pg tpejvn dzbopcpspizesjef.)