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1) 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.)

2) Hydration of but-1-yne

By addition of water on but-1-yn, the compound is formed which is a subject of isomerization. Draw the structure of the first compound and consequently of the final product.



(Enciphered hint 1: Beejujpo pg xbufs up b usjqmf cpoe. Uif sfbdujpo qspdffet bddpsejoh up Nbslpwojlpw't svmf. )


(Enciphered hint 1: Uif fopm gpsnfe jo uif sfbdujpo voefshpft jtpnfsjabujpo up uif dpssftqpoejoh pyp-gpsn.)

3) 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.)

4) Acetylene

Draw the structure of acetylene.


(Enciphered hint 1: Fuizof.)

5) Ozonolysis of unknown alkyne (3)

The given compounds are the products of ozonolysis of an alkadiyne. Draw its structure.



(Enciphered hint 1: Dbscpyzmjd gvodujpot bsf gpsnfe cz dmfbwbhf pg usjqmfu cpoet.)

6) Propargyl chloride

Draw the structure of propargyl chloride.


(Enciphered hint 1: 3-Dimpspqspq-1-zof.)

7) Ozonolysis of oct-4-yne

Write the products of ozonolysis of the alkyne shown in the picture.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg usjqmf cpoe voefs gpsnbujpo pg dbscpyzmjd hspvqt.)

8) Methyl phenyl ketone with sodium acetylide

Draw the product of the reaction of methyl phenyl ketone with sodium acetylide followed by the reaction with diluted sulfuric acid.



(Enciphered hint 1: Uif gjstu tufq jt beejujpo pg bdfuzmjef bojpo up uif dbscpozmf hspvq. Uif tfdpoe tufq jt bdjepcbtjd sfbdujpo pg uif bmdpipmbuf xjui ejmvufe tvmgvsjd bdje.)

9) 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.)

10) Acetaldehyde with sodium methylacetylide

Acetaldehyde reacts with sodium methylacetylide to form a salt. Draw the structure of the salt. Then draw structure of subsequent reaction with diluted sulfuric acid.



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


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

11) Diphenyl ketone with sodium acetylide

Diphenyl ketone reacts with sodium acetylide to form a salt. Draw the structure of the salt. Then draw structure of subsequent reaction with diluted sulfuric acid.



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


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

12) Reaction of but-1-yne with hydrogen chloride

Draw the product of the reaction of but-1-yne with one equivalent of hydrogen chloride.



(Enciphered hint 1: Fmfduspqijmjd beejujpo xijdi qspdffet bddpsejoh up Nbslpwojlpw't svmf.)

13) Synthesis of 3-phenylpropan-2-one from alkyne.

Draw the structure of alkyne giving by hydration the following ketone.



(Enciphered hint 1: Beejujpo pg xbufs gpmmpxfe cz jtpnfsjabujpo pg qsjnbsjmz gpsnfe beevdu.)
(Enciphered hint 2: Uif qptjujpo pg uif usjqmf cpoe qmbzt bo jnqpsubou spmf jo uif sfbdujpo: ufsnjobm bmlzoft pomz hjwf nfuizm lfupoft.)

14) Reaction of but-1-yne with chlorine

Draw the product of the reaction of but-1-yne with two equivalents of chlorine.



(Enciphered hint 1: Beejujpo pg uxp npmfdvmft pg dimpsjof up b nvmujqmf cpoe.)

15) Ozonolysis of cyclooctyne

Write the products of ozonolysis of the alkyne shown in the picture.



(Enciphered hint 1: Pyjebujwf dmfbwbhf pg usjqmf cpoe voefs gpsnbujpo pg dbscpyzmjd hspvqt.)

16) Ozonolysis of unknown alkyne (1)

The given compounds are the products of ozonolysis of an alkyne. Draw its structure.



(Enciphered hint 1: Dbscpyzmjd gvodujpot bsf gpsnfe cz pyjebujwf dmfbwbhf pg b usjqmf cpoe.)

17) Ozonolysis of unknown alkyne (2)

The given compounds are the products of ozonolysis of an alkyne. Draw its structure.



(Enciphered hint 1: Dbscpyzmjd hspvq jt gpsnfe cz pyjebujwf dmfbwbhf pg usjqmf cpoe.)

18) Bromopropane with sodium acetylide

Draw the product of sodium acetylide with 1-bromopropane.



(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo po bmlzm ibmjef. Bdfuzmjef jpo jt b ovdmfpqijmf.)

19) Oxidation of oct-4-yne

Draw the products of the reaction of oct-4-yne with potassium permanganate in alcaline medium followed by acidification.



(Enciphered hint 1: Pyjebujpo pg nvmujqmf cpoe.)

20) Reaction of but-1-yne with hydrogen chloride (2)

Draw the product of the reaction of but-1-yne with two equivalents of hydrogen chloride.



(Enciphered hint 1: Epvcmf fmfduspqijmjd beejujpo. Uif sfbdujpo qspdffet bddpsejoh up Nbslpwojlpw't svmf.)

21) 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.)

22) Reaction of but-2-yne with chlorine

Draw the product of the reaction of but-2-yne with one equivalent of chlorine. Consider the stereochemistry of the reaction.



(Enciphered hint 1: Bouj-beejujpo pg dimpsjof up b usjqmf cpoe.)

23) Acetone with sodium cyclohexylacetylide

Acetone reacts with sodium cyclohexylacetylide to form a salt. Draw the structure of the salt. Then draw structure of subsequent reaction with diluted sulfuric acid.



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


(Enciphered hint 1: Bdje-cbtf sfbdujpo.)

24) Benzaldehyde with sodium phenylacetylide

Draw the product of the reaction of benzaldehyde with sodium phenylacetylide followed by the reaction with diluted sulfuric acid.



(Enciphered hint 1: Uif gjstu tufq jt beejujpo pg bdfuzmjef bojpo up uif dbscpozmf hspvq. Uif tfdpoe tufq jt bo bdje-cbtf sfbdujpo pg uif bmdpipmbuf xjui ejmvufe tvmgvsjd bdje.)

25) 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.)

26) Cyclopentanone with sodium phenylacetylide

Draw the product of the reaction of cyclopentanone with sodium phenylacetylide followed by the reaction with diluted sulfuric acid.



(Enciphered hint 1: Uif gjstu tufq jt beejujpo pg bdfuzmjef bojpo up uif dbscpozmf hspvq. Uif tfdpoe tufq jt bo bdje-cbtf sfbdujpo pg uif bmdpipmbuf xjui ejmvufe tvmgvsjd bdje.)

27) Propyne reacts with organometallic and then with acetone

Propyne reacts with butylmagnesium bromide to form a salt. Then draw the structure of the product of a subsequent reaction with acetone, after work-up with diluted sulfuric acid.



(Enciphered hint 1: Bdje-cbtf sfbdujpo.)


(Enciphered hint 1: Uif gjstu tufq jt beejujpo pg bdfuzmjef bojpo up uif dbscpozmf hspvq. Uif tfdpoe tufq jt bo bdje-cbtf sfbdujpo pg uif bmdpipmbuf xjui ejmvufe tvmgvsjd bdje.)

28) 4-Propargylbenzoic acid

Draw the structure of 4-propargylbenzoic acid.


(Enciphered hint 1: Qspqbshzm = qspq-2-zo-1-zm)

29) 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.)

30) 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.)

31) Reaction of 3-phenylprop-1-yne with an excess of hydrogen chloride

Draw the product of the reaction of 3-phenylprop-1-yne with an excess of hydrogen chloride. At first, draw the product of addition of the first and then of the second molecule od hydrogen chloride.



(Enciphered hint 1: Fmfduspqijmjd beejujpo. Sfhjptfmfdujwjuz dpssftqpoet up qbsujbm dibshf bu dbscpot dpoofdufe cz usjqmf cpoet.)


(Enciphered hint 1: Bmtp uif tfdpoe beejujpo ublft qmbdf cz fmfduspqijmjd nfdibojtn xjui uif sfhjptfmfdujwjuz dpssftqpoejoh up qbsujbm dibshf bu dbscpo bupnt po epvcmf cpoe.)

32) Hydration of hex-1-yne

By addition of water on hex-1-yne, the compound is formed which is a subject of isomerization. Draw the structure of the first compound and consequently of the final product.



(Enciphered hint 1: Beejujpo pg xbufs up b usjqmf cpoe. Uif sfbdujpo qspdffet bddpsejoh up Nbslpwojlpw't svmf. )


(Enciphered hint 1: Uif fopm gpsnfe jo uif sfbdujpo voefshpft jtpnfsjabujpo up uif dpssftqpoejoh pyp-gpsn.)

33) Pent-1-en-4-yne

Draw the structure of pent-1-en-4-yne.


(Enciphered hint 1: Opuf uif qptjujpo pg nvmujqmf cpoet.)

34) Synthesis of 1-phenylpent-1-yne

Alkynes can be prepared by alkylation of acetylene or terminal alkynes. Draw the structure of alkyne to be alkylated in the synthesis of 1-phenylpent-1-yne.



(Enciphered hint 1: Dpotjefs gpsnbujpo pg dbscpo dibjo.)

35) Ozonolysis of hex-2-yne

Draw the products of ozonolysis of the alkyne shown in the picture.



(Enciphered hint 1: Pyjebujpo pg uif usjqmf cpoe mfbejoh up uif dpssftqpoejoh dbscpyzmjd bdjet.)

36) Synthesis of hexan-3-one from alkyne.

Draw the structure of alkyne affording the following ketone by hydration as a single product.



(Enciphered hint 1: Pomz tznnfusjd bmlzof dbo hjwf uijt tjohmf qspevdu.)

37) Synthesis of 1-phenyl-3,3-dichlorbutane from alkyne.

Draw the structure of alkyne giving by the reaction with HCl the following dichloro derivative as a single product.



(Enciphered hint 1: Dpotjefs sfhjptfmfdujwjuz pg beejujpo.)

38) Ozonolysis of but-1-yne

Draw the products of ozonolysis of the alkyne shown in the picture.



(Enciphered hint 1: Pyjebujpo pg uif usjqmf cpoe mfbejoh up uif dpssftqpoejoh dbscpyzmjd bdjet.)

39) Hydroboration/oxidation of alkyne

By reaction of but-1-yne with borane followed by oxidation with hydrogen peroxide under basic conditions, the compound is formed which is a subject of isomerization. Draw the structure of the first compound and consequently of the final product.



(Enciphered hint 1: Esbx qsjnbsz qspevdu cfgpsf jtpnfsjabujpo.)


(Enciphered hint 1: Pyp-fopm ubvupnfsjabujpo.)

40) Hydroboration/oxidation of alkyne (2)

By reaction of 3-phenylprop-1-yne with borane followed by oxidation with hydrogen peroxide under basic conditions, the compound is formed which is a subject of isomerization. Draw the structure of the first compound and consequently of the final product.



(Enciphered hint 1: Esbx qsjnbsz qspevdu cfgpsf jtpnfsjabujpo.)


(Enciphered hint 1: Pyp-fopm ubvupnfsjabujpo.)

41) 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.)

42) 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.)

43) Hydroboration/oxidation of alkyne (3)

By reaction of 1,2-dicyclohexylacetylene with borane followed by oxidation with hydrogen peroxide under basic conditions, the compound is formed which is a subject of isomerization. Draw the structure of the primary product and consequently of the final product.



(Enciphered hint 1: Esbx uif qsjnbsz qspevdu pg izesbujpo cfgpsf jtpnfsjabujpo.)


(Enciphered hint 1: Pyp-fopm ubvupnfsjabujpo.)