1. The label has fallen off a bottle containing a sugar with the formula C6H the unknown sugar at both ends gives an optically active dicarboxylic ac pyranose of the unknown sugar is found to contain two axdal substituem structure that represents the original sugar in the bottle. CHO CHO HO HO HO CH HO CH CH CH,CH CH by CH,CH

1. The label has fallen off a bottle containing a sugar with the formula C6H the unknown sugar at both ends gives an optically active dicarboxylic ac pyranose of the unknown sugar is found to contain two axdal substituem structure that represents the original sugar in the bottle. CHO CHO HO HO HO CH HO CH CH CH,CH CH by CH,CH

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.67P: Treatment of -D-glucose with methanol in the presence of an acid catalyst converts it into a mixture...

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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.
Fats can be either optically active or optically inactive, depending on their structure. Draw the structure of an optically active fat that yields 2 equivalents of stearic acid and 1 equivalent of oleic acid on hydrolysis. Draw the structure of an optically inactive fat that yields the same products.
Treatment of either anomer of fructose with excess ethanol in the presence of a trace ofHCl gives a mixture of the a and b anomers of ethyl-d-fructofuranoside. Draw the startingmaterials, reagents, and products for this reaction. Circle the aglycone in each product
Hyaluronic acid, a component of connective tissue, is the fluid that lubricates joints. It is a polymer of alternating N-acetyl-d-glucosamine and d-glucuronic acid subunits joined by β-1,3'-glycosidic linkages. Draw a short segment of hyaluronic acid.
Ignoring stereoisomers, draw the two possible enols for butan-2-one (CH3COCH2CH3), and predict which one is more stable.
DHA is a fatty acid derived from sh oil and an abundant fatty acid in vertebrate brains. Hydrogenation of DHA forms docosanoic acid [CH3(CH2)20CO2H] and ozonolysis forms CH3CH2CHO, CH2(CHO)2 (ve equivalents), and HCOCH2CH2CO2H. What is the structure of DHA if all double bonds have the Z conguration?
4-Chloro-2-pentene has a double bond that can have either the E or the Z configuration and a stereogenic center that can have either the R or the S configuration. How many stereoisomers arepossible altogether? Draw the structure of each, and group the pairs of enantiomers.
In the Cr6+ oxidation of cyclohexanols, it is generally true that stericallyhindered alcohols react faster than unhindered alcohols. Which of the attached alcohols should be oxidized more rapidly?
What are the reagents used to convert 2-butyne to C4H8? What are the products when that C4H8 is mixed with OsO4, and H2O (the formula will be C4H10O2 racemic)? What is the product when C4H8 is mixed with RCO3H, and H2O (the formula will be C4H10O2 meso)?
When some sugars dissolve in water they spontaneously undergo changes in optical rotation called mutarrotation. The Mutarrotation of D-glucopyranose is catalyzed by acid and bases. 2-Hydroxypyridine is a more effective catalyst than phenol and pyridine for this reaction because: a.Both oxygen and N in 2-hydroxypyridine act as bases increasing the rapid interconversion of sugar b. The OH of 2-hydroxypyridine serves as the base while the current N as the acid. c. 2-hydroxypyridine acts both as a base to remove the proton from the hydroxyl group in the hemiacetal and as an acid to provide a proton to the oxygen in the hemiacetal. d.Phenol and pyridine are very expensive.
#B: Methyl acetate has methoxy, -OCH3 as the remaining of the alcohol part in the ester. Isopropyl acetate has isopropoxy, -OCH(CH3)2 as the remaining of the alcohol part in the ester. -OCH(CH3)2 is more electron donating than the methoxy, -OCH3 group due to the presence of two electron-donating -CH3 group in the former. Hence saponification reaction of Isopropyl acetate is much slower than methyl acetate. Hence the rate of saponification of methyl acetate, CH3CCO2CH3 is 50 times greater than that for isopropyl acetate.
What product is formed when D-Gulose is treated with a. CH3I, Ag2O b. The product in (a), then H3O+ c. The product in (b), then C6H5CH2Cl, Ag2O