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1) E,Z isomerism 3

Draw the structural formula of (E)-oct-4-ene.


(Enciphered hint 1: Uif F tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

2) E,Z isomerism 6

Draw the structural formula of (Z)-3-bromo-3-chloro-2-(trifluoromethyl)prop-2-en-1-ol.


(Enciphered hint 1: Uif [ tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

3) Fischer projection of 2-bromo-3-chlorobutane

Draw a three-dimensional structural formula of the given compound.


(Enciphered hint 1: Jo b Gjtdifs qspkfdujpo, bmm ipsjapoubm cpoet qspkfdu upxbset uif wjfxfs, xijmf uif wfsujdbm cpoet qspkfdu bxbz gspn uif wjfxfs.)

4) Meso form

Draw a three-dimensional structural formula of the meso stereoisomer of the compound shown.



(Enciphered hint 1: B nftp gpsn jt b dpnqpvoe xijdi ibt tufsfdfousft cvu jt bdijsbm.)

5) Stereochemistry 1

Draw three-dimensional structure of (S)-2-methylpentanoic acid.


(Enciphered hint 1: Vtf xfehf boe ebtife mjof up esbx cpoet up ofbsfs boe gvsuifs bupn.)

6) (2R,3S)-Butane-2,3-diol

Draw the three-dimensional structural formula of (2R,3S)-butane-2,3-diol.


(Enciphered hint 1: Vtf xfehft boe ebtife mjoft up esbx cpoet up ofbsfs boe gvsuifs bupnt.)

7) Absolute configuration of 2-bromo-3-chlorobutane

Draw the three-dimensional structural formula of (2R,3R)-2-bromo-3-chlorobutane.


(Enciphered hint 1: Qbz buufoujpo up uif sjhiu qptjujpo pg uif cpoet po tufsfpdfousft.)

8) E,Z isomerism 2

Draw the structural formula of (E)-2,3-dichlorohex-2-ene.


(Enciphered hint 1: Uif F tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

9) Preparation of dibromoderivative

Draw the starting alkene suitable for the preparation of dibromoderivative using bromine.



(Enciphered hint 1: Bouj-beejujpo pg cspnjof.)

10) Enantiomer 2

Draw a three-dimensional structural formula of the enantiomer of the given compound.



(Enciphered hint 1: Bo foboujpnfs ibt uif pqqptjuf dpogjhvsbujpo po bmm uif tufsfphfojd dfousft.)

11) D-Erythrose

Draw the three-dimensional structural formula of D-erythrose.


(Enciphered hint 1: E-fszuisptf ((2S,3S)-2,3,4-usjizespyzcvubobm) jt b ufusptf dbscpizesbuf.)

12) Absolute configuration of 1-bromo-2-chlorocyclopropane

Draw a three-dimensional structural formula of (1R,2R)-1-bromo-2-chlorocyclopropane.

(Enciphered hint 1: Qbz buufoujpo up uif sjhiu qptjujpo pg uif cpoet po tufsfpdfousft.)

13) D-Galactopyranose

Draw the three-dimensional structural formula of beta-D-galactopyranose.


(Enciphered hint 1: Qzsboptf jt pof pg uif dzdmjd gpsnt pg tbdibsjeft. Bmgb boe cfub bttjho uif dpogjhvsbujpo bu uif bopnfsjd dbscpo.)
(Enciphered hint 2: Cfub-bopnfsjd IP-hspvq po uif dbscpo bupn D1 ibt usbot psjfoubujpo jo sfmbujpo up uif pyzhfo bupn po uif dbscpo bupn D5 jo Gjtdifs qspkfdujpo.)

14) Maltose

Draw the three-dimensional structural formula of maltose.


(Enciphered hint 1: Nbmuptf jt b ejtbdibsjef gpsnfe pg uxp vojut pg hmvdptf.)

15) Ethyl-alpha-L-mannopyranoside

Draw the three-dimensional structural formula of ethyl-alpha-L-mannopyranoside.


(Enciphered hint 1: Qzsboptjef jt bo bdfubm pg uif dzdmjd gpsnt pg tbddibsjeft. Bmqib-bopnfsjd FuP-hspvq po uif dbscpo bupn D1 ibt djt psjfoubujpo jo sfmbujpo up uif pyzhfo bupn po uif dbscpo bupn D5 jo Gjtdifs qspkfdujpo.)

16) Methyl-alpha-D-galactofuranoside

Draw the three-dimensional structural formula of methyl-alpha-D-galactofuranoside.


(Enciphered hint 1: Gvsboptjef jt bo bdfubm pg uif dzdmjd gpsnt pg tbddibsjeft. Bmqib-bopnfsjd NfP-hspvq po uif dbscpo bupn D1 ibt djt psjfoubujpo jo sfmbujpo up uif pyzhfo bupn po uif dbscpo bupn D5 jo Gjtdifs qspkfdujpo.)

17) Fischer projection 2

Draw a three-dimensional structural formula of the given compound.



(Enciphered hint 1: Jo b Gjtdifs qspkfdujpo, bmm ipsjapoubm cpoet qspkfdu upxbset uif wjfxfs.)

18) Absolute configuration 6

Draw the three-dimensional structural formula of L-alanine.


(Enciphered hint 1: M-bmbojof jt (T)-2-bnjopqspqbopjd bdje.)

19) Absolute configuration of 3-iodohexane

Draw the structure of (R)-3-iodohexane.

(Enciphered hint 1: Tufsfpeftdsjqups S tqfdjgjft uif dpogjhvsbujpo po b tufsfphfojd dfousf (ifsf b dbscpo bupn cfbsjoh gpvs ejggfsfou tvctujuvfout).)

20) (2R,3R)-Butane-2,3-diol

Draw the three-dimensional structural formula of (2R,3R)-butane-2,3-diol.


(Enciphered hint 1: Vtf xfehft boe ebtife cpoet up esbx dpoofdujpot up ofbsfs boe gvsuifs bupnt. )

21) E,Z isomerism 5

Draw the structural formula of (E)-3-tert-butylpent-3-en-1-ol.


(Enciphered hint 1: Uif F tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

22) Nomenclature XI

Draw the three-dimensional structural formula of (1R,2R,5S)-2-isopropyl-5-methylcyclohexane-1-thiol. Use wedged bonds to indicate the position of the substituents.


(Enciphered hint 1: B tpmje xfehf sfqsftfout cpoe upxbset uif sfbefs boe b ebtife mjof b sfdfejoh cpoe.)

23) Enantiomer 3

Draw a three-dimensional structural formula of the enantiomer of the compound shown.



(Enciphered hint 1: Bo foboujpnfs ibt uif pqqptjuf dpogjhvsbujpo po bmm uif tufsfpdfousft.)

24) D-Arabinose

Draw the three-dimensional structural formula of D-arabinose.


(Enciphered hint 1: E-Bsbcjoptf ((2T,3S,4S)-2,3,4,5-ufusbizespyzqfoubobm) jt b qfouptf dbscpizesbuf.)

25) L-Mannopyranose

Draw the three-dimensional structural formula of beta-L-mannopyranose.


(Enciphered hint 1: Qzsboptf jt pof pg uif dzdmjd gpsnt pg tbdibsjeft. Bmgb boe cfub bttjho uif dpogjhvsbujpo bu uif bopnfsjd dbscpo.)

26) Absolute configuration 5

Draw the three-dimensional structural formula of (2R,3R)-tartaric acid.


(Enciphered hint 1: Ubsubsjd bdje jt 2,3-ejizespyzcvubofejpjd bdje.)

27) Nomenclature V

Draw the three-dimensional structural formula of (R)-3,5-dihydroxy-3-methylpentanoic acid.


(Enciphered hint 1: Vtf xfehf boe ebtife mjof gps cpoet up ofbsfs boe gvsuifs bupnt, sftqfdujwfmz.)

28) Methyl-beta-D-galactopyranoside

Draw the three-dimensional structural formula of methyl-beta-D-galactopyranoside.


(Enciphered hint 1: Qzsboptjef jt bo bdfubm pg uif dzdmjd gpsnt pg tbddibsjeft. Cfub-bopnfsjd NfP-hspvq po uif dbscpo bupn D1 ibt usbot psjfoubujpo jo sfmbujpo up uif pyzhfo bupn po uif dbscpo bupn D5 jo Gjtdifs qspkfdujpo.)

29) Trans-1-sec-butyl-2-methylcyclopentane

Draw the three-dimensional structure of trans-1-sec-butyl-2-methylcyclopentane. Use wedged bonds to indicate the position of the substituents.


(Enciphered hint 1: B tpmje xfehf sfqsftfout cpoe upxbset uif sfbefs boe b ebtife mjof b sfdfejoh cpoe.)

30) 1,4-Dimethylcyclohexane

Draw the three-dimensional structure of the compound shown below. Use wedged bonds to indicate the position of the methyl groups.



(Enciphered hint 1: B tpmje xfehf sfqsftfout cpoe upxbset uif sfbefs boe b ebtife mjof b sfdfejoh cpoe.)

31) Structure to name (1)

Name the following structure:



(Enciphered hint 1: Ju jt b dijsbm dpnqpvoe, ju jt ofdfttbsz up vtf Dbio-Johpme-Qsfmph qsjpsjuz svmft.)

32) Absolute configuration of 2,3-dibromohexane

Draw the three-dimensional structural formula of threo-2,3-dibromohexane.

(Enciphered hint 1: Tufsfp eftdsjqupst uisfp tqfdjgjft uif sfmbujwf dpogjhvsbujpo po tufsfphfojd dfousft.)
(Enciphered hint 2: Uif dpnqpvoe ibt uxp foboujpnfst.)

33) Configuration of 2,3-dibromopentane

Draw the three-dimensional structural formula of (2R,3S)-2,3-dibromopentane.


34) E,Z isomerism 4

Draw the structural formula of (E)-2-(bromomethyl)-3-methylhept-2-enal.


(Enciphered hint 1: Uif F tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

35) Diastereomer 2

Draw three-dimensional structural formulae of the diastereomers of the compound in the picture.



(Enciphered hint 1: B ejbtufsfpnfs jt b tufsfpjtpnfs xijdi jt opu foboujpnfs. Ju ejggfst jo uif dpogjhvsbujpo po pof ps npsf tufsfpdfousft, cvu opu po bmm pg uifn.)

36) 2-Bromopentane with sodium iodide

Use a three-dimensional structural formula and draw (S)-2-bromopentane and the product of its reaction with sodium iodide in acetone.

(Enciphered hint 1: Difdl dpogjhvsbujpo po tufsfphfojd dfoufs.)


(Enciphered hint 1: Ovdmfpqijmjd tvctujuvujpo xjui jpejef bojpo. Qbz buufoujpo up uif tufsfpdifnjdbm dpvstf pg uif sfbdujpo.)

37) E,Z isomerism 1

Draw the structural formula of (Z)-3,4-dimethylhex-3-ene.


(Enciphered hint 1: Uif [ tufsfp eftdsjqups joejdbuft uif epvcmf cpoe dpogjhvsbujpo.)

38) Fischer projection

Draw a three-dimensional structural formula of the given compound.



(Enciphered hint 1: Jo b Gjtdifs qspkfdujpo, bmm ipsjapoubm cpoet qspkfdu upxbset uif wjfxfs.)

39) Diastereomer

Draw three-dimensional structural formula of the diastereomers of the compound in the picture.



(Enciphered hint 1: B ejbtufsfpnfs jt b tufsfpjtpnfs xijdi jt opu foboujpnfs. Ju ejggfst jo uif dpogjhvsbujpo po pof ps npsf tufsfpdfousft, cvu opu po bmm pg uifn.)

40) D-Ribofuranose

Draw the three-dimensional structural formula of beta-D-ribofuranose.


(Enciphered hint 1: Gvsboptf jt pof pg uif dzdmjd gpsnt pg tbdibsjeft. Bmgb boe cfub bttjho uif dpogjhvsbujpo bu uif bopnfsjd dbscpo.)

41) Reaction of but-1-ene with chlorine (2)

Draw both enantiomers of the product formed by the reaction of but-1-ene with one equivalent of chlorine.



(Enciphered hint 1: Foboujpnfst ejggfst cz uif dpogjhvsbujpo po tufsfphfojd dfoufs.)

42) Diastereomer 3

Draw three-dimensional structural formula of the diastereomer of cyclohexan-1,2-diamine.



(Enciphered hint 1: B ejbtufsfpnfs jt b tufsfpjtpnfs xijdi jt opu foboujpnfs. Ju ejggfst jo uif dpogjhvsbujpo po pof ps npsf tufsfpdfousft, cvu opu po bmm pg uifn.)

43) Preparation of diol with given configuration

Draw the starting alkene suitable for the preparation of the racemic mixture of diols by oxidation using OsO4.



(Enciphered hint 1: Tzo-izespyzmbujpo pdvsst.)

44) Trans-1,3-dimethylcyclohexane

Draw trans-1,3-dimethylcyclohexane in three-dimensional structure. Use wedged bonds to indicate the position of the methyl groups.


(Enciphered hint 1: B tpmje xfehf sfqsftfout b cpoe upxbset uif sfbefs boe b ebtife mjof b sfdfejoh cpoe.)

45) Ephedrine

Draw the structure of (1R,2S)-2-(methylamino)-1-phenylpropan-1-ol.


(Enciphered hint 1: Vtf gvmm xfehf cpoe boe ebtife mjof up dpoofdu ofbsfs boe gvsuifs bupnt.)

46) Pseudoephedrine

Draw the structure of (1R,2R)-2-(methylamino)-1-phenylpropan-1-ol.


(Enciphered hint 1: Vtf gvmm xfehf cpoe boe ebtife mjof up dpoofdu ofbsfs boe gvsuifs bupnt.)

47) Absolute configuration 1

Draw the three-dimensional structural formula of (R)-butan-2-ol.


(Enciphered hint 1: Tufsfpeftdsjqups S tqfdjgjft uif dpogjhvsbujpo po b tufsfphfojd dfousf (ifsf b dbscpo bupn cfbsjoh gpvs ejggfsfou tvctujuvfout).)

48) Absolute configuration 2

Draw the three-dimensional structural formula of (S)-but-3-en-2-ol.


(Enciphered hint 1: Tufsfpeftdsjqups T tqfdjgjft uif dpogjhvsbujpo po b tufsfphfojd dfousf (ifsf b dbscpo bupn cfbsjoh gpvs ejggfsfou tvctujuvfout).)

49) Enantiomer

Draw a three-dimensional structural formula of the enantiomer of the compound in the picture.



(Enciphered hint 1: Bo foboujpnfs ibt bo pqqptjuf dpogjhvsbujpo po bmm uif tufsfphfojd dfousft.)

50) Structure to name (2)

Name the following structure:



(Enciphered hint 1: Ju jt b dijsbm dpnqpvoe, ju jt ofdfttbsz up vtf Dbio-Johpme-Qsfmph qsjpsjuz svmft.)

51) Cis-1,3-dimethylcyclohexane

Draw the three-dimensional structure of cis-1,3-dimethylcyclohexane. Use wedged bonds to indicate the position of the methyl groups.


(Enciphered hint 1: B tpmje xfehf sfqsftfout cpoe upxbset uif sfbefs boe b ebtife mjof b sfdfejoh cpoe.)

52) Absolute configuration 7

Draw the three-dimensional structural formula of (R)-2-methylpiperidine.


(Enciphered hint 1: Tufsfpeftdsjqups S tqfdjgjft uif dpogjhvsbujpo po b tufsfphfojd dfousf (ifsf b dbscpo bupn cfbsjoh gpvs ejggfsfou tvctujuvfout).)

53) Preparation of diol with given configuration (2)

Draw the starting alkene suitable for the preparation of diol by oxidation using OsO4.



(Enciphered hint 1: Tzo-izespyzmbujpo pg epvcmf cpoe.)

54) Cis-1-isobutyl-4-methylcyclohexane

Draw the three-dimensional structure of cis-1-isobutyl-4-methylcyclohexane. Use wedged bonds to indicate the position of the substituents.


(Enciphered hint 1: B tpmje xfehf sfqsftfout cpoe upxbset uif sfbefs boe b ebtife mjof b sfdfejoh cpoe.)

55) 1,2-Dimethylcyclohexane

Draw the three-dimensional structure of the compound shown below. Use wedged bonds to indicate the position of the methyl groups.



(Enciphered hint 1: B tpmje xfehf sfqsftfout cpoe upxbset uif sfbefs boe b ebtife mjof b sfdfejoh cpoe.)