EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 20, Problem 44P
Interpretation Introduction
Interpretation:
The identification of compound A and B is to be stated.
Concept Introduction:
Sodium borohydride is a strong reducing agent. It reduces an
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
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.
Aldohexoses A and B are formed from aldopentose C via a Kiliani–Fischer synthesis. Nitric acid oxidizes A to an optically active aldaric acid, B to an optically inactive aldaric acid, and C to an optically active aldaric acid. Wohl degradation of C forms D, which is oxidized by nitric acid to an optically active aldaric acid. Wohl degradation of D forms (+)-glyceraldehyde. Identify A, B, C, and D.
Which D-aldopentose is oxidized to an optically active aldaric acid and undergoes the Wohl degradation to yield a Daldotetrose that is oxidized to an optically active aldaric acid?
Chapter 20 Solutions
EBK ORGANIC CHEMISTRY
Ch. 20.1 - Prob. 1PCh. 20.2 - Prob. 2PCh. 20.2 - Prob. 3PCh. 20.3 - Prob. 4PCh. 20.3 - Prob. 5PCh. 20.3 - Prob. 6PCh. 20.4 - Prob. 7PCh. 20.4 - Prob. 8PCh. 20.5 - Prob. 9PCh. 20.5 - Prob. 10P
Ch. 20.5 - Prob. 11PCh. 20.6 - Prob. 12PCh. 20.6 - Prob. 13PCh. 20.6 - Prob. 14PCh. 20.7 - Prob. 15PCh. 20.8 - Prob. 16PCh. 20.9 - Prob. 18PCh. 20.10 - Prob. 20PCh. 20.10 - Prob. 21PCh. 20.10 - Prob. 22PCh. 20.11 - Prob. 23PCh. 20.11 - Prob. 24PCh. 20.12 - Prob. 25PCh. 20.12 - Prob. 26PCh. 20.14 - Prob. 28PCh. 20.15 - Prob. 29PCh. 20.15 - Prob. 30PCh. 20.16 - Prob. 31PCh. 20.17 - Prob. 32PCh. 20.18 - Refer to Figure 20.5 to answer the following...Ch. 20 - Prob. 34PCh. 20 - Prob. 35PCh. 20 - Prob. 36PCh. 20 - Prob. 37PCh. 20 - Prob. 38PCh. 20 - Prob. 39PCh. 20 - Prob. 40PCh. 20 - Prob. 41PCh. 20 - Prob. 42PCh. 20 - Prob. 43PCh. 20 - Prob. 44PCh. 20 - Prob. 45PCh. 20 - Prob. 46PCh. 20 - Prob. 47PCh. 20 - Prob. 48PCh. 20 - The 1H NMR spectrum of D-glucose in D2O exhibits...Ch. 20 - Prob. 50PCh. 20 - Prob. 51PCh. 20 - Prob. 52PCh. 20 - Prob. 53PCh. 20 - Prob. 54PCh. 20 - Prob. 55PCh. 20 - Prob. 56PCh. 20 - Prob. 57PCh. 20 - Prob. 58PCh. 20 - Prob. 59PCh. 20 - Prob. 60PCh. 20 - Prob. 61PCh. 20 - A hexose is obtained when the residue of a shrub...Ch. 20 - Prob. 63PCh. 20 - Prob. 64PCh. 20 - Prob. 65PCh. 20 - Prob. 66PCh. 20 - Prob. 67PCh. 20 - Prob. 68PCh. 20 - Prob. 69PCh. 20 - Prob. 70PCh. 20 - Prob. 71PCh. 20 - Prob. 72PCh. 20 - Prob. 73P
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- A D-aldopentose A is reduced to an optically active alditol. Upon Kiliani–Fischer synthesis, A is converted to two D-aldohexoses, B and C. B is oxidized to an optically inactive aldaric acid. C is oxidized to an optically active aldaric acid. What are the structures of A–C?arrow_forwardA D-aldopentose A is oxidized to an optically inactive aldaric acid with HNO3. A is formed by the Kiliani–Fischer synthesis of a D-aldotetrose B, which is also oxidized to an optically inactive aldaric acid with HNO3. What are the structures of A and B?arrow_forwardMonosaccharide A is a diastereomer of d-lyxose. Treatment of A with nitric acid forms an optically inactive aldaric acid. A undergoes a Kiliani-Fischer synthesis to form B and C. B is oxidized by nitric acid to an optically active aldaric acid, and C is oxidized to an optically inactive aldaric acid. Wohl degradation of A forms D, which is oxidized by nitric acid to an optically inactive aldaric acid. Wohl degradation of D forms a d-aldotriose. Identify A, B, C, and D.arrow_forward
- What two aldohexoses yield D-arabinose upon Wohl degradation?arrow_forward(a) Which of the d-aldopentoses will give optically active aldaric acids on oxidation with HNO3 ?(b) Which of the d-aldotetroses will give optically active aldaric acids on oxidation with HNO3 ?(c) Sugar X is known to be a d-aldohexose. On oxidation with HNO3, X gives an optically inactive aldaric acid. WhenX is degraded to an aldopentose, oxidation of the aldopentose gives an optically active aldaric acid. Determine thestructure of X.(d) Even though sugar X gives an optically inactive aldaric acid, the pentose formed by degradation gives an opticallyactive aldaric acid. Does this finding contradict the principle that optically inactive reagents cannot form opticallyactive products?(e) Show what product results if the aldopentose formed from degradation of X is further degraded to an aldotetrose.Does HNO3 oxidize this aldotetrose to an optically active aldaric acid?arrow_forwardTreatment with NaBH 4 converts aldose U into an optically inactive (meso) alditol V. Ruff degradation ofU gives W, whose alditol is optically inactive. Ruff degradation of W forms D-glyceraldehyde, thesimplest aldose. Upon Kiliani-Fischer synthesis, U is converted to two aldoses, X and Y. X is oxidized toan optically active aldaric acid Z. Y is oxidized to an optically inactive aldaric acid. Draw the structuresof D-glyceraldehyde, V, W, X, Y, and Z. Structure of compound U is shown below.arrow_forward
- What two aldoses yield D-xylose on Wohl degradation?arrow_forwardWhat aldoses are formed when the following aldoses are subjected to the Kiliani–Fischer synthesis: (a) d-threose; (b) dribose; (c) D-galactose?arrow_forwardThere are three (3) vials labeled A, B, and C known to contain the following monosaccharides. All three samples reduce Tollens and Fehling. By oxidation with dilute HNO3 an optically active aldaric acid is obtained for sample A and the remaining two give products without optical activity. When the three samples were subjected to an alkaline medium, it was observed that, after a certain time, samples A and C reached the same value of the specific rotation [α]. Select the RIGHT alternative: (a) Sample A is Galactose. (b) Sample B is Alosa. (c) Samples A and C are not related to each other by an epimerization process. (d) Sample C is Talose. (e) Samples B and C are epimers.arrow_forward
- Monosaccharide A is a D-aldotetrose. Treatment of A with nitric acid gives an optically inactive aldaric acid (B). Killiani-Fischer chain extension of A gives two products (C & D). C on treatment with NABH4, gives an alditol (E) that is optically active. D gives an alditol (F) that is NOT optically active. Give Fischer projections for A, B, CD, E, and E.arrow_forward14) Which of the following descriptions apply to both dihydroxyacetone and D-fructofuranose? I. They are both ketoses. II. They are both aldoses. III. They are enatiomers of each other. IV. They are diastereomers of each other. V. They are epimers of each other. A) I B) II C) I and III D) II and IV E) II, IV and Varrow_forwardВ. 1. Draw the Fischer, Haworth & chair (where applicable) representations of the given monosaccharides. Sugar Fischer Haworth Chair a CHO но H- H но OH ČH2OH D-idose (а-anomer) CH2OH FOH H- ČH2OH a ketopentose (B-anomer) b.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
