Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Question
Chapter 24.4, Problem 4P
Interpretation Introduction
Interpretation:
The D, L configuration, the R, S configuration at the chirality center with the highest number of the given aldose are to be determined. The sign of rotation of the aldose is also to be predicted.
Concept introduction:
A carbon atom that has four non-equivalent atoms or groups attached to it is known as a chiral carbon atom (or asymmetric or stereogenic centers).
The naming of a chiral center and geometric isomers are based on Cahn-Ingold-Prelog priority rules.
The D and L configuration are the spatial arrangement of the molecules about the chirality center of the carbohydrates.
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Treatment with sodium borohydride converts aldose A to an optically inactive alditol. Wohl degradation of A forms B, whose alditol is optically inactive. Wohl degradation of B forms d-glyceraldehyde. Identify A and B.
Devise a synthesis of CH3CH2CH2CHO from two-carbon starting materials. Draw both the retrosynthesis and the forward synthesis.
Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a D-aldotetrose that is oxidized to an optically active aldaric acid?
Chapter 24 Solutions
Organic Chemistry - Standalone book
Ch. 24.2 - Prob. 1PCh. 24.3 - Problem 24.2 Which aldotetrose in the structure...Ch. 24.4 - Prob. 3PCh. 24.4 - Prob. 4PCh. 24.6 - Prob. 5PCh. 24.6 - Prob. 6PCh. 24.7 - Prob. 7PCh. 24.8 - Prob. 8PCh. 24.8 - Prob. 9PCh. 24.9 - Prob. 10P
Ch. 24.10 - Prob. 11PCh. 24.10 - Prob. 12PCh. 24.11 - Prob. 13PCh. 24.12 - Prob. 14PCh. 24.14 - Prob. 15PCh. 24.14 - Prob. 16PCh. 24.14 - Prob. 17PCh. 24.14 - Using Mechanism 24.2 as a guide, write a stepwise...Ch. 24.15 - Prob. 19PCh. 24.17 - Prob. 20PCh. 24.17 - Prob. 21PCh. 24.18 - Prob. 22PCh. 24.18 - Prob. 23PCh. 24.18 - Prob. 24PCh. 24.20 - Prob. 25PCh. 24 - Prob. 26PCh. 24 - Prob. 27PCh. 24 - Prob. 28PCh. 24 - Prob. 29PCh. 24 - Prob. 30PCh. 24 - Prob. 31PCh. 24 - Prob. 32PCh. 24 - Prob. 33PCh. 24 - Prob. 34PCh. 24 - Prob. 35PCh. 24 - Methyl glycosides of 2-deoxy sugars have been...Ch. 24 - Prob. 37PCh. 24 - Prob. 38PCh. 24 - Prob. 39PCh. 24 - Prob. 40PCh. 24 - Treatment of d-mannose with methanol in the...Ch. 24 - Prob. 42PCh. 24 - Prob. 43PCh. 24 - Prob. 44PCh. 24 - Prob. 45DSPCh. 24 - Prob. 46DSPCh. 24 - Prob. 47DSPCh. 24 - Prob. 48DSPCh. 24 - Prob. 49DSP
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- Draw the Configuration of the D-Family of Aldoses in a short bond paper (fit in 1 page only) Label properly, thank you!arrow_forwardDraw a stepwise mechanism for the conversion of β-D-glucose to both anomers of N-ethyl glucopyranoside, the equation written in Reaction [1].arrow_forwardWhich of the compounds are achiral? Identify the relationship of A with BCD.arrow_forward
- Draw both pyranose anomers of each aldohexose using a threedimensionalrepresentation with a chair pyranose. Label each anomer asα or β.arrow_forwardThe following isomerization reaction, drawn using D-glucose as starting material, occurs with all aldohexoses in the presence of base. Draw a stepwise mechanism that illustrates how each compound is formed.arrow_forwardUnderstanding monosaccharides (2-part problem) a) Draw both anomers of the 4C1 and 1C4 chairs of D-mannapyranose. Rank them from least stable to most stable, justifying your choice. b) Draw the acid-catalysed mechanism whereby D-fructose cyclizes to α-D-fructofuranosearrow_forward
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