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Draw the following monosaccharides, using chair conformations for the pyranoses and Haworth projections for the furanoses.

(a)Dmannopyranose(C2epimerofglucose)(b)Dgalactopyranose(C4epimerofglucose)(c)Dallopyranose(C3epimerofglucose)(d)Darabinofuranose(e)Dribofuranose(C2epimerofarabinose)

Short Answer

Expert verified

(a)

Dmannopyranose

(b)

Dgalactopyranose

(c)

Dallopyranose

(d)

Darabinofurinose

(e)

Dribofuranose

Step by step solution

01

Pyranose, furanose, Epimers and Anomers

Pyranose is a six-membered cyclic hemiacetal while a furanose is a five-membered cyclic hemiacetal.

Epimers are sugars with a common structure, such as the arrangement of H and OH around carbon atoms, except for the carbon present at position or carbon number 2. Glucose and mannose, for example, are epimers of each other.

Anomers are the diastereomers that result during cyclization. Only the arrangement surrounding the first carbon C1, referred known as the anomeric carbon, differs (hemiacetal carbon atom).

02

Identifying α‐and β‐  anomers of pyranoses and furanoses

For anomer, hydroxy group (-OH) on the anomeric carbon is down (axial position) while for anomer, hydroxy group (-OH) on the anomeric carbon is up (equatorial position). Again, for anomer, the anomeric hydroxy(-OH) group is placed trans to the terminal -CH2OHgroup while for anomer, the anomeric hydroxy (-OH) group is placed cis to the terminalCH2OH group.

03

Structure of monosaccharides

(a) In chair conformation of Dmannopyranose, the anomeric carbon is C1 . The hydroxy group (-OH) on the anomeric carbon is down (axial position).

Dmannopyranose

In chair conformation of Dgalactopyranose, the anomeric carbon is C1. The hydroxy group (-OH) on the anomeric carbon is up (equatorial position).

Dgalactopyranose

(c) In chair conformation of Dalllopyranose, the anomeric carbon is C1 . The hydroxy group (-OH) on the anomeric carbon is up (equatorial position).


Dallopyranase

(d) In Haworth projection of Darabinofuranose, the anomeric carbon is C1. The hydroxy group (-OH) on the anomeric carbon is down which is trans to the terminal CH2OHgroup

Darabinofuranose

(e) In Haworth projection of , the anomeric carbon is . The hydroxy group on the anomeric carbon is up which is cis to the terminal CH2OHgroup.


Dribofuranose

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Most popular questions from this chapter

a) Draw D-allose, the C3 epimer of glucose.

b) Draw D-talose, the C2 epimer of D-galactose.

c) Draw D-idose, the C3 epimer of D-talose. Now compare your answers with Figure 23-3.

d) Draw the C4 鈥渆pimer鈥 of D-xylose. Notice that this 鈥渆pimer鈥 is actually an L-series sugar, and we have seen its enantiomer. Give the correct name for this L-series sugar.

Question. (a) Figure 23-2 shows that the degradation of D-glucose gives D-arabinose, an aldopentose. Arabinose is most stable in its furanose form. Draw D-arabinofuranose.

(b) Ribose, the C2 epimer of arabinose, is most stable in its furanose form. Draw D-ribofuranose.

Predict the products obtained when D-galactose reacts with each reagent.

(a) Br2 and H2O

(b) NaOH,H2O

(c)CH3OH, H+

(d) Ag(NH3)+2OH+

(e) H2, Ni

(f) excess Ac2O and pyridine

(g) excess CH3I ,Ag2O

(h) NaBH4

(i) Br2 , H2O then H2O2 and Fe2(SO4)3

(j) (1) KCN/HCN; (2) H2 Pd/BaSO4; (3) H3O+

(k)excess HIO4

Cytosine, uracil and guanine have tautomeric forms with aromatic hydroxyl groups. Draw these tautomeric forms.

In 1891, Emil Fischer determined the structures of glucose and seven other D-aldohexoses using only simple chemical reactions and clever reasoning about stereochemistry and symmetry. He received the Nobel Prize for this work in 1902. Fischer has determined that D-glucose is an aldohexose, and he used Ruff degradation to degrade it to (+)-glyceraldehyde. Therefore, the eight D-aldohexose structures shown in Figure 23-3 are the possible structures for glucose.

Pretend that no names are shown in Figure 23-3 except for glyceraldehyde, and sue the following results to prove which of these structures represent glucose, mannose, arabinose, and erythrose.

(a)Upon Ruff degradation, glucose and mannose gives the same aldopentose: arabinose.Nitric acid oxidation of arabinose gives an optically active aldaric acid. What are the two possible structures of arabinose?

(b) Upon Ruff degradation, arabinose gives the aldotetrose erythrose. Nitric acid oxidation of erythrose gives an optically inactive aldaric acid, meso-tartaric acid. What is the structure of erythrose?

(c) Which of the two possible structures of arabinose is correct? What are the possible structures of glucose and mannose?

(d) Fischer鈥檚 genius was needed to distinguish between glucose and mannose. He developed a series of reactions to convert the aldehyde group of an aldose to an alcohol while converting the terminal alcohol to an aldehyde. In effect, he swapped the functional groups on the ends. When he interchanged the functional groups on D-mannose, he was astonished to find that the product was still D-mannose. Show how this information completes the proof of the mannose structure, and show how it implies the correct glucose structure.

(e) When Fischer interchanged the functional groups on D-glucose, the product was an unnatural L sugar. Show which unnatural sugar he must have formed, and show how it completes the proof of the glucose structure.

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