Essential Organic Chemistry, Global Edition
3rd Edition
ISBN: 9781292089034
Author: Paula Yurkanis Bruice
Publisher: PEARSON
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Chapter 16.5, Problem 7P
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 16 Solutions
Essential Organic Chemistry, Global Edition
Ch. 16.1 - Prob. 1PCh. 16.2 - Prob. 2PCh. 16.3 - Prob. 3PCh. 16.3 - Prob. 4PCh. 16.4 - Prob. 5PCh. 16.4 - Prob. 6PCh. 16.5 - Prob. 7PCh. 16.5 - Prob. 8PCh. 16.6 - Prob. 10PCh. 16.8 - Prob. 12P
Ch. 16.8 - Prob. 14PCh. 16.9 - Prob. 15PCh. 16.10 - Prob. 16PCh. 16.11 - Refer to Figure 16.4 to answer the following...Ch. 16 - Prob. 18PCh. 16 - Prob. 19PCh. 16 - Prob. 20PCh. 16 - Prob. 21PCh. 16 - Prob. 22PCh. 16 - Prob. 23PCh. 16 - Prob. 24PCh. 16 - Prob. 25PCh. 16 - Name the following compounds:Ch. 16 - Prob. 28PCh. 16 - Prob. 29PCh. 16 - Prob. 31PCh. 16 - Prob. 32PCh. 16 - Prob. 33PCh. 16 - Prob. 34PCh. 16 - Prob. 35PCh. 16 - Prob. 36PCh. 16 - Prob. 37PCh. 16 - Draw the mechanism for the acid-catalyzed...Ch. 16 - Prob. 39PCh. 16 - Prob. 40PCh. 16 - Prob. 41P
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- How many types of stereoisomers are possible for a ketohexose molecule? Draw structures of all possible stereoisomers. Structures should be neat and cleararrow_forwardConvert attached cyclic monosaccharide to its acyclic form.arrow_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
- For the following disaccharide, identify acetal/ketal carbons and glycosidic linkage: ge НО Н�� ОН ОН Но ОН ОН ОНarrow_forwardAssign a name to the following monosaccharide. Use D and Ldesignation. CHO HO H HO H Но- HOH ČH2OHarrow_forwardDraw the structures of an aldopentose and a ketohexose.arrow_forward
- In glycoside formation, the hemiacetal functional group of a cyclic monosaccharide is converted to an acetal group by reaction with a(an)arrow_forwardUsing fructose and glucose as examples explain the concept of chirality?arrow_forwardTwo molecules of glucose, a monosaccharide, when joined together they form a molecule of maltose. Write a chemical reaction to show this process.arrow_forward
- An important step in the glycolysis pathway for catabolizing glucose is the hydride transfer from an hemithioacetal to the acceptor NAD*. Indicate with curved arrows the flow of electrons in this step. Enzyme Enzyme BH* B: H H-O-H H- OH `NH2 H- -OH NH2 CH,OPO,2 CH,OPO, Hemithioacetal Thioesterarrow_forwardβ-Galactosidase is an enzyme that hydrolyses only β(1,4) linkages of lactose. An unknown trisaccharide is converted by β-galactosidase into maltose and galactose. Draw the structure of the trisaccharide.arrow_forwardUsing appropriate prefixes/infixes/suffixes (ketoheptose, aldoheptose, etc.) to classify each ofthe monosaccharides shown below.arrow_forward
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