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1) D-Xylose with bromine

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



(Enciphered hint 1: Pyjebujpo pg uif dbscpozm hspvq ublft qmbdf. Bmepojd bdje jt gpsnfe.)

2) 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.)

3) Kiliani-Fischer synthesis

What products would you expect from Kiliani-Fischer reaction of D-xylose? Draw the three-dimensional structure of their open-chain form.



(Enciphered hint 1: Uxp bmepifyptft ejggfsjoh jo uifjs tufsfpdifnjtusz bu D2 dbscpo.)

4) D-Xylofuranose with acetic anhydride

Draw the three-dimensional structure of the product of the reaction of beta-D-xylofuranose with acetic anhydride in the presence of pyridine.



(Enciphered hint 1: Bmm uif -PI hspvqt sfbdu.)

5) 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.)

6) 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.)

7) D-Glucose with HNO3

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



(Enciphered hint 1: Pyjebujpo pg uif dbscpo bupnt D1 boe D6 ublft qmbdf. Bmebsjd bdje jt gpsnfe.)

8) Maltose

Draw the three-dimensional structural formula of maltose.


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

9) 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.)

10) 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.)

11) 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.)

12) Synthesis of D-arabinaric acid

Which pentose gives the same aldaric acid as D-arabinose on oxidation with nitric acid? Draw the three-dimensional structure of its open-form.



(Enciphered hint 1: Ju jt bopuifs E-qfouptf.)
(Enciphered hint 2: E-Mzyptf.)

13) Kiliani-Fischer synthesis 2

What aldopentose would give a mixture of D-galactose and D-talose on Kiliani-Fischer synthesis? Draw the three-dimensional structure of its open-chain form.



(Enciphered hint 1: Uif Ljmjboj-Gjtdifs tzouiftjt sftvmut jo uif dibjo mfohuifojoh cz pof dbscpo bupn. Uif -DIP hspvq cfdpnft uif D2 jo uif gpsnfe ifyptf.)

14) 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.)

15) Synthesis of D-glucaric acid

Which hexose gives the same aldaric acid as D-glucose on oxidation with nitric acid? Draw the three-dimensional structure of its open-form.



(Enciphered hint 1: Jut bo M-ifyptf.)
(Enciphered hint 2: M-Hvmmptf.)

16) 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.)

17) Wohl degradation

What product would you expect from Wohl degradation of D-altrose? Draw the three-dimensional structure of the open-chain form.



(Enciphered hint 1: Xpim efhsbebujpo tipsufot uif bmeptf cz pof dbscpo bupn.)

18) 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.)

19) D-Allopyranose with acetic anhydride

Draw the three-dimensional structure of the product of the reaction of beta-D-allopyranose with acetic anhydride in the presence of pyridine.



(Enciphered hint 1: Bmm uif -PI hspvqt sfbdu.)

20) D-Allose with bromine

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



(Enciphered hint 1: Pyjebujpo pg uif dbscpozm hspvq ublft qmbdf. Bmepojd bdje jt gpsnfe.)

21) 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.)

22) D-Mannopyranose with methanol

Draw the three-dimensional structure of the products of the reaction of beta-D-mannopyranose with methanol in the presence of acid catalyst.



(Enciphered hint 1: Uif sfbdujpo qspdffet bu uif bopnfsjd dbscpo.)

23) D-Allopyranose with methanol

Draw the three-dimensional structure of the products of the reaction of alfa-D-allopyranose with methanol in the presence of acidic catalyst.



(Enciphered hint 1: Uif sfbdujpo qspdffet bu uif bopnfsjd dbscpo pomz.)

24) L-Arabinose with HCN

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



(Enciphered hint 1: Beejujpo up uif dbscpozm hspvq zjfmet b njyuvsf pg ejbtufsfpjtpnfst pg dzbopizesjot.)

25) 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.)

26) Wohl degradation 2

What aldohexoses would give D-arabinose on Wohl degradation? Draw the three-dimensional structures of their open-chain forms.



(Enciphered hint 1: Xpim efhsbebujpo tipsufot uif bmeptf cz pof dbscpo bupn.)

27) D-Talopyranose with acetic anhydride

Draw the three-dimensional structure of the product of the reaction of alpha-D-talopyranose with acetic anhydride in the presence of pyridine.



(Enciphered hint 1: Bmm uif -PI hspvqt sfbdu.)

28) L-Allose with HNO3

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



(Enciphered hint 1: Pyjebujpo pg uif dbscpo bupnt D1 boe D6 ublft qmbdf. Bmebsjd bdje jt gpsnfe.)
(Enciphered hint 2: Jo uijt dbtf, nftp-bmmbsjd bdje jt gpsnfe. Fjuifs E- ps M-bmmptf dbo cf vtfe bt tubsujoh dpnqpvoet gps uijt pyjebujpo sfbdujpo.)

29) D-Gulopyranose with methyl iodide

Draw the three-dimensional structure of the product of the reaction of beta-D-gulopyranose with methyl iodide and silver(I) oxide.



(Enciphered hint 1: Bmm uif -PI hspvqt sfbdu.)

30) D-Allopyranose with methyl iodide

Draw the three-dimensional structure of the product of the reaction of alpha-D-allopyranose with methyl iodide and silver(I) oxide.



(Enciphered hint 1: Bmm uif -PI hspvqt sfbdu.)