Under acidic conditions (catalytic amount of acid) in anhydrous methanol, D-galactosecan be converted to the methyl galactopyranoside X on the right side of the reactionarrow. Write a detailed mechanism for the reaction.OHH+HOHO`MeMeOHHO'OHHO"OHOHOHX

Step 1: D-Galactose to methyl glucopyranoside reaction:In the given reaction, the monosaccharide has…

Answered: Under acidic conditions (catalytic…

Organic Chemistry

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Chapter22: Carbonyl Alpha-substitution Reactions

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Problem 30MP: One of the later steps in glucose biosynthesis is the isomerization of fructose 6-phosphate to...

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Give the major organic product that is formed when the primary hydroxyl group of the following monosaccharide undergo nucleophilic substitution reaction with acetic anhydride
Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-membered, five-membered, or six-membered ring. To determine which ring is formed, ribose is treated with methanol in the presence of an acid catalyst. The products are then isolated and treated with NaIO, then with H₂O*. HO OH OH OH Ribose, C5H10O5 H 9.81 ** MeOH H* A & B isomeric cyclic acetals with formula C6H12O5 Assuming that ribose formed a five-membered ring cyclic hemiacetal, draw the structure of the sodium periodate digestion products. ▼ • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. 1. NalO4, 2. H₂O* MeOH products 4 SIF Previous Next
Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four- membered, five-membered, or six-membered ring. To determine which ring is formed, ribose is treated with methanol in the presence of an acid catalyst. The products are then isolated and treated with NaIO4 then with H3O+. OH HO OH OH Ribose, C5H10O5 H MeOH H* A & B isomeric cyclic acetals with formula C6H₁2O5 1. NalO4 2. H₂O* MeOH products Assuming that ribose formed a six-membered ring cyclic hemiacetal, draw the structure of the sodium periodate digestion products. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
a) Give the main organic product for the following reaction: CH2OH OH H30* CH3CH2CH2OH OH OH OH b) Give the major product that is formed when the primary hydroxyl group of the following monosaccharide reacts with acetic anhydride. CH2OH Но Но OH OH c) Give the major organic product for the reaction shown below. CHO Но HNO3 НО НО CH2OH
Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-membered, five-membered, or six-membered ring. To determine which ring is formed, ribose is treated with methanol in the presence of an acid catalyst. The products are then isolated and treated with NaIO4 then with H30*. OH Меон 1. NalO4 2. H30* A & B MEOH + products HO H. H* isomeric cyclic acetals with formula CgH1205 ÕH ÕH Ribose, C5H1005 Assuming that ribose formed a six-membered ring cyclic hemiacetal, draw the structure of compounds A and B.
The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture of two compounds called methyl glucosides (Section 25.3A). In these representations, the six-membered rings are drawn as planar hexagons. (a) Propose a mechanism for this conversion and account for the fact that only the OH on carbon 1 is transformed into an OCH3 group. (b) Draw the more stable chair conformation for each product. (c) Which of the two products has the chair conformation of greater stability? Explain.
The structures of an aldose and a ketose are shown here. An aldose contains an aldehyde group. Click on that group.
Myo-inositol, the most prominent naturally occurring form of inositols, is a carbocyclic polyol that plays an important role as the structural basis for a number of secondary messengers in eukaryotic cells. It is generated in vivo from the aldol cyclization of glucose-6-phosphate to myo-inositol-1-phosphate
Ribose, a carbohydrate with the formula shown, forms a cyclic hemiacetal, which, in principle, could contain either a four-membered, five-membered, or six-membered ring. To determine which ring is formed, ribose is treated with methanol in the presence of an acid catalyst. The products are then isolated and treated with NalO, then with H30*. он MEOH 1. NalO. 2. H,O* A & B MEOH + products HO H* isomeric cyclic acetals with formula CgH1205 ÕH Ribose, CSH1005
HO НО- CH OH OH -ОН + CH₂CCH₂ нст tas \OH 2. Glucose and Mannose can be interconverted by treatment with dilute sodium hydroxid Provide a mechanism for this reaction.
CH3 Ph3P-CHCH3 H3C H3C Aldehydes and ketones are converted into alkenes by means of a direct nucleophilic addition called the Wittig reaction. In the reaction, a triphenylphosphorine ylide, also called a phosphorane, adds to an aldehyde/ketone to give a four-membered cyclic intermediate called an oxaphosphetane. The oxaphosphetane is not isolated but instead spontaneously decomposes to release triphenylphosphine oxide and an alkene. Ph3P-CHCH3 H3C The ylide is formed by reaction of triphenylphosphine, a good nucleophile, with a primary alkyl halide in an S 2 reaction, followed by deprotonation of the carbon with a strong base, such as butyllithium. The carbonyl carbon and the carbon originally bonded to the halogen become the two carbons with the double bond in the product alkene :0: CH3 Com The real value of the Wittig reaction lies in its ability to yield an alkene of predictable structure, as the C-C bond is precisely where the C=O bond was in the reactant and no isomers (other than…

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Under acidic conditions (catalytic amount of acid) in anhydrous methanol, D-galactose can be converted to the methyl galactopyranoside X on the right side of the reaction arrow. Write a detailed mechanism for the reaction. OH H+ HO HO `Me MeOH HO 'OH HO "OH OH OH X