Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Question
Chapter 21.5, Problem 9P
Interpretation Introduction
Interpretation:
The enediol rearrangement of the carbonyl carbon of fructose from
Concept Introduction:
In the enediol rearrangement of a monosaccharide, the base removes the proton from the carbon resulting in the formation of enolate ion. After the deprotonation, enediol is formed resulting in the formation of aldohexose and ketohexose by the base-catalyzed conversion.
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Chapter 21 Solutions
Organic Chemistry
Ch. 21.1 - Prob. 1PCh. 21.2 - Prob. 2PCh. 21.2 - Prob. 3PCh. 21.3 - Prob. 4PCh. 21.3 - Prob. 5PCh. 21.3 - Prob. 6PCh. 21.4 - Prob. 7PCh. 21.4 - Prob. 8PCh. 21.5 - Prob. 9PCh. 21.5 - Prob. 10P
Ch. 21.5 - Prob. 11PCh. 21.6 - Prob. 12PCh. 21.6 - Prob. 13PCh. 21.6 - Prob. 14PCh. 21.7 - Prob. 15PCh. 21.8 - Prob. 16PCh. 21.9 - Prob. 18PCh. 21.10 - Prob. 20PCh. 21.10 - Prob. 21PCh. 21.10 - Prob. 22PCh. 21.11 - Prob. 24PCh. 21.11 - Prob. 25PCh. 21.15 - Prob. 27PCh. 21.16 - Prob. 28PCh. 21.17 - Prob. 29PCh. 21.18 - Refer to Figure 20.5 to answer the following...Ch. 21 - Prob. 31PCh. 21 - Prob. 32PCh. 21 - Prob. 33PCh. 21 - Prob. 34PCh. 21 - Prob. 35PCh. 21 - Prob. 36PCh. 21 - Prob. 37PCh. 21 - Prob. 38PCh. 21 - Prob. 39PCh. 21 - Prob. 40PCh. 21 - Prob. 41PCh. 21 - Prob. 42PCh. 21 - Prob. 43PCh. 21 - Prob. 44PCh. 21 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 21 - Prob. 46PCh. 21 - Prob. 47PCh. 21 - Prob. 48PCh. 21 - Prob. 49PCh. 21 - Prob. 50PCh. 21 - Prob. 51PCh. 21 - Prob. 52PCh. 21 - Prob. 53PCh. 21 - Prob. 54PCh. 21 - Prob. 55PCh. 21 - A hexose is obtained when the residue of a shrub...Ch. 21 - Prob. 57PCh. 21 - Prob. 58PCh. 21 - Prob. 59PCh. 21 - Prob. 60PCh. 21 - Prob. 61PCh. 21 - Prob. 62PCh. 21 - Prob. 63PCh. 21 - Prob. 64PCh. 21 - Prob. 65PCh. 21 - Prob. 66P
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- Draw the chemical structures of the two cyclic monosaccharides that result from the enzymatic hydrolysis of maltose. In the structures, CIRCLE the hydrogens and oxygen that came from water during the hydrolysis reaction.arrow_forwardFor the following disaccharide, identify acetal/ketal carbons and glycosidic linkage: ge НО Н�� ОН ОН Но ОН ОН ОНarrow_forwardThe term milk sugar and table sugar correspond to which disaccharides: o lactose and maltose o lactose and sucrose o lactose and cellobiose o maltose and sucrosearrow_forward
- How many types of stereoisomers are possible for a ketohexose molecule? Draw structures of all possible stereoisomers. Structures should be neat and cleararrow_forwardDraw the structure of: a polysaccharide formed by joining D-glucose units in 1→6-α-glycosidic linkages.arrow_forwardwhat is the structure digested by and how many reducing sugars are present ОН ОН Но OH HO Но HO- OH HO, The trisaccharide pictured could be completely digested (ie into monomers) by a beta-galactosidase and an alpha-glucosidase an alpha-galactosidase and sucrase lactase and sucrase a beta-fructosidase and lactasearrow_forward
- Using fructose and glucose as examples explain the concept of chirality?arrow_forwarddoes structure E represent ketohexose. explainarrow_forwardO aldopentose Question 3 Classify the following monosaccharide. C-H HO H- -HO- HO H- CH3 carboxylic acid heptose O alcohol pentose O ketohexose O deoxyhexose O aldohexose Question 4arrow_forward
- Identify the anomeric carbon. Identify the glycosidic linkage. Lactose ОН ОН OH HO HO, HO OHarrow_forwardWhen d-tagatose is added to a basic aqueous solution, an equilibrium mixture of monosaccharides is obtained, two of which are aldohexoses and two of which are ketohexoses. Identify the aldohexoses and ketohexoses.arrow_forward
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