Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 22, Problem 13PP
Interpretation Introduction
Interpretation:
The structure of L-(+)-threose and L-(+)-erythrose is to be represented and the aldotriose, which must be used for the preparation of the above-mentioned compounds in the Kiliani-Fischer synthesis, is to be determined.
Concept Introduction:
▸ The Kiliani-Fischer reaction is used for increasing the number of carbon atoms of an aldose molecule, as a result of the formation of the epimeric aldonic acid.
▸ It is an effective and economic process for the synthesis of monosaccharides by the process of hydrolysis of a cyanohydrin.
▸ Furthermore, it can also be used for the production of epimers of higher aldoses from a lower aldose, that is, a single aldose produces a mixture of two diastereomeric sugars called epimers.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Aldohexoses A and B both undergo Ruff degradation to give aldopentose C. On treatment with warm nitric acid, aldopentose C gives an optically active aldaric acid. B alsoreacts with warm nitric acid to give an optically active aldaric acid, but A reacts to givean optically inactive aldaric acid. Aldopentose C is degraded to aldotetrose D, whichgives optically active tartaric acid when it is treated with nitric acid. Aldotetrose D isdegraded to (+)@glyceraldehyde. Deduce the structures of sugars A, B, C, and D, and useFigure 23-3 to determine the correct names of these sugars.
When the gum of the shrub Sterculia setigera is subjected to acidic hydrolysis, one of the water-soluble components of thehydrolysate is found to be tagatose. The following information is known about tagatose:(1) Molecular formula C6H12O6(2) Undergoes mutarotation.(3) Does not react with bromine water.(4) Reduces Tollens reagent to give d-galactonic acid and d-talonic acid.(5) Methylation of tagatose (using excess CH3 I and Ag2O) followed by acidic hydrolysis gives1,3,4,5-tetra-O-methyltagatose.(a) Draw a Fischer projection structure for the open-chain form of tagatose.(b) Draw the most stable conformation of the most stable cyclic hemiacetal form of tagatose
22.46 (a&d only)
Chapter 22 Solutions
Organic Chemistry
Ch. 22 - Prob. 1PPCh. 22 - Prob. 2PPCh. 22 - Prob. 3PPCh. 22 - Prob. 4PPCh. 22 - Prob. 5PPCh. 22 - Prob. 6PPCh. 22 - Prob. 7PPCh. 22 - Prob. 8PPCh. 22 - Practice Problem 22.9 What products would you...Ch. 22 - Prob. 10PP
Ch. 22 - Prob. 11PPCh. 22 - Prob. 12PPCh. 22 - Prob. 13PPCh. 22 - Prob. 14PPCh. 22 - Prob. 15PPCh. 22 - Prob. 16PPCh. 22 - Prob. 17PPCh. 22 - Prob. 18PPCh. 22 - Prob. 19PPCh. 22 - Prob. 20PCh. 22 - Prob. 21PCh. 22 - Prob. 22PCh. 22 - Prob. 23PCh. 22 - Prob. 24PCh. 22 - Prob. 25PCh. 22 - Prob. 26PCh. 22 - Prob. 27PCh. 22 - Prob. 28PCh. 22 - Prob. 29PCh. 22 - Prob. 30PCh. 22 - Prob. 31PCh. 22 - Prob. 32PCh. 22 - Prob. 33PCh. 22 - Prob. 34PCh. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - Prob. 37PCh. 22 - Prob. 38PCh. 22 - Arbutin, a compound that can be isolated from the...Ch. 22 - Prob. 40PCh. 22 - Prob. 41PCh. 22 - Prob. 42PCh. 22 - Prob. 43PCh. 22 - 22.44 The following reaction sequence represents...Ch. 22 - 22.45
The NMR data for the two anomers...Ch. 22 - Shikimic acid is a key biosynthetic intermediate...
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
- (i) Why do actinoids show wide range of oxidation states? (ii) Why is actinoid contraction greater than lanthanoid contraction?arrow_forward(a) Isoleucine has been prepared by the following sequence of reactions. Give the structure of compounds A through D isolated as intermediates in this synthesis.(b) An analogous procedure has been used to prepare phenylalanine. What alkyl halide would you choose as the starting material for this synthesis?arrow_forward6. Give the product of the following reactions: (a) a-d-allopyranose (b) a-d-talopyranose (c) B-d-gulopyranose + excess acetic anhydride and NaOAc + excess dimethyl sulfate + hydrogen gas and a platinum catalyst.arrow_forward
- 3a. 3b. 3c 3d. 3e. CO₂ clavulanic acid CH₂-OH H Answer the following questions about clavulanic acid. Does clavulanic acid inhibit D-alanyl-D-alanine transpeptidase? Does clavulanic acid contain a ß-lactam? Does clavulanic acid contain a thiazolium ring? What is the result of the treatment of penicillinase with clavulanic acid? Does clavulanic acid form a covalent acyl-enzyme intermediate with penicillinase?arrow_forward25. What is the major product of the following substitution? (a) (c) NaOPh 2-chlorobutane (b) (d) Šarrow_forward(b) Suggest a reasonable biosynthesis for the naturally occurring alkaloid coniine (isolated from hemlock), starting from octanoic acid. Coniinearrow_forward
- Identify the hemiacetal function in lactose and show mechanistically how the stereochemistry at that carbon can easily invert, especially in the presence of acids and bases.arrow_forwardDraw the structures of the following.arrow_forwardA tripeptide contains lysine (R= -(CH₂)4NH₂), phenylalanine (R= -CH₂C6H5) and glycine (R= -H). It was found that the tripeptide reacts with 2 moles of DNFB to give compound A. When compound A was treated with SOCI2, glycine was activated. When hydrolyzed, both NH₂ groups of lysine were found to be DNP-labelled. What is the structure of the tripeptide? Select one: H (CH₂)2NH2 CH NH CH H₂N O O H₂N H₂N H₂N C (CH2)4NH2 CH 010 (CH2)4NH2 CH C=O CH,Ph CH NH NH NH CH CH,Ph CH H 010 CH CH,Ph CH (CH2)4NH2 ΝΗ NH NH NH CH,Ph CH H CH COOH H CH COOH COOH COOHarrow_forward
- (a) Why are alkyl halides insoluble in water? (b) Why is Butan-l-ol optically inactive but Butan-2-ol is optically active? (c) Although chlorine is an electron withdrawing group, yet it is ortho-, Para- directing in electrophilic aromatic substitution reaction. Why?arrow_forward(a) Provide (Draw) products for the following reactions OH OH 1. PCC 2. t-BuPh₂SiCl DMAP,CH₂Cl2arrow_forwardIdentify the carbon atoms expected to be labeled with 14C when each is biosynthesized from acetate enriched with 14C in its methyl group.(a) Palmitic acid(b) PGE2(c) PGI2(d) Limonene(e) β-Carotenearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning