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Draw the expected product of the reaction of the following sugars with excess methyl iodide and silver oxide.

  1. 伪-顿-蹿谤耻肠迟辞蹿耻谤补苍辞蝉别
  2. 尾-顿-驳补濒补肠迟辞辫测谤补苍辞蝉别

Short Answer

Expert verified
  1. methyl 2,3,4,6,-tetra-O-methyl-伪-D-fructofuranoside
  2. methyl 2,3,4,6,-tetra-O-methyl-尾-D-fructofuranoside


Step by step solution

01

Formation of methyl ether

Hydroxy groups of sugar can be converted to methyl ethers by treating with methyl iodide (CH3I) and silver oxide (Ag2O). CH3-I group can be polarised by silver oxide (Ag2O), which makes the methyl carbon more strongly electrophilic. Attack by the -OH group of carbohydrate is then followed by deprotonation which gives the ether.

02

Pyranose and furanose

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

03

Formation of product

  1. 伪-顿-蹿谤耻肠迟辞蹿耻谤补苍辞蝉别 on treatment with excess methyl iodide and silver oxide gives methyl 2,3,4,6, -tetra-O-methyl-伪-D-fructofuranoside as the product.
  2. 尾-顿-驳补濒补肠迟辞辫测谤补苍辞蝉别 on treatment with excess methyl iodide and silver oxide gives methyl 2,3,4,6,-tetra-O-methyl-尾-D-galactopyranoside as the product.

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Most popular questions from this chapter

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)

(a) Show the product that results when fructose is treated with an excess of methyl iodide and silver oxide.

(b) Show what happens when the product of part (a) is hydrolyzed using dilute acid.

(c) What do the results of parts (a) and (b) imply about the hemiacetal structure of fructose?

Erwin Chargaff鈥檚 discovery that DNA contains equimolar amounts of guanine and cytosine and also equimolar amounts of adenine and thymine has come to be known as Chargaff鈥檚 rule:

G = C and A = T

(a) Does Chargaff鈥檚 rule imply that equal amounts of guanine and adenine are present in DNA? That is, does G = A?

(b) Does Chargaff鈥檚 rule imply that the sum of the purine residues equals the sum of the pyrimidine residues? That is, does A + G = C + T?

(c) Does Chargaff鈥檚 rule apply only to double-stranded DNA, or would it also apply to each individual strand if the double helical strand were separated into its two complementary strands?

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

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.

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