KLEIN'S ORGANIC CHEMISTRY
3rd Edition
ISBN: 9781119423126
Author: Klein
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Question
Chapter 24.6, Problem 37CC
Interpretation Introduction
Interpretation:
The reagents used to convert D-ribose into D-erythrose should be determined.
Concept introduction:
The Wohl degradation: aldoses is reaction with hydroxylamine and sodium methoxide which yields oxime then resultant oxime is reaction with acetic anhydride in acetic acid with sodium acetate which afforded chain shortened nitrile. In this reaction step the oxime is converted into the nitrile with simultaneous conversion of all the alcohol groups to acetate groups. Finally, sodium methoxide in methanol is added to the reaction which yields the final degradation compound.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
20.17 Predict the structure of the major product formed by 1,2-addition of HBr to
3-methylenecyclohexene.
3-Methylenecyclohexene
20.18 Predict the major product formed by 1,4-addition of HBr to 3-methylenecyclohexene.
+
Draw a vicinal alkyl bromide that would produce the following alkene in an E2
elimination. Use a dash or wedge bond to indicate stereochemistry on
asymmetric centers, where applicable. Ignore any inorganic byproducts.
Br
Drawing
Strong Base
H
Q
Atoms, Bonds
Charges
and Rings
Draw or tap a new bond to see suggestions.
Remove
Done
語
Reset
Undo
+
Drag To Pan
Draw a vicinal alkyl bromide that would produce the following alkene in an
E2 elimination. Use a dash or wedge bond to indicate stereochemistry on
asymmetric centers, where applicable. Ignore any inorganic byproducts.
+
Drawing
Į
Strong Base
H
Br
Q
Atoms, Bonds
and Rings
Charges
Draw or tap a new bond to see suggestions.
Undo
Reset
謂
Remove
Done
Drag To Pan
+
Chapter 24 Solutions
KLEIN'S ORGANIC CHEMISTRY
Ch. 24.2 - Prob. 1CCCh. 24.2 - Prob. 2CCCh. 24.2 - Prob. 3CCCh. 24.2 - Prob. 4CCCh. 24.2 - Prob. 5CCCh. 24.2 - Prob. 6CCCh. 24.4 - Prob. 7CCCh. 24.4 - Prob. 8CCCh. 24.5 - Prob. 1LTSCh. 24.5 - Prob. 9PTS
Ch. 24.5 - Prob. 10ATSCh. 24.5 - Prob. 11ATSCh. 24.5 - Prob. 2LTSCh. 24.5 - Prob. 12PTSCh. 24.5 - Prob. 13PTSCh. 24.5 - Prob. 14ATSCh. 24.5 - Prob. 15ATSCh. 24.5 - Prob. 3LTSCh. 24.5 - Prob. 16PTSCh. 24.5 - Prob. 17ATSCh. 24.5 - Prob. 18ATSCh. 24.5 - Prob. 19CCCh. 24.5 - Prob. 20CCCh. 24.5 - Prob. 21CCCh. 24.5 - Prob. 22CCCh. 24.6 - Prob. 23CCCh. 24.6 - Prob. 24CCCh. 24.6 - Prob. 25CCCh. 24.6 - Prob. 26CCCh. 24.6 - Prob. 27CCCh. 24.6 - Prob. 28CCCh. 24.6 - Prob. 29CCCh. 24.6 - Prob. 30CCCh. 24.6 - Prob. 4LTSCh. 24.6 - Prob. 31PTSCh. 24.6 - Prob. 32ATSCh. 24.6 - Prob. 33ATSCh. 24.6 - Prob. 34CCCh. 24.6 - Prob. 35CCCh. 24.6 - Prob. 36CCCh. 24.6 - Prob. 37CCCh. 24.6 - Prob. 38CCCh. 24.7 - Prob. 5LTSCh. 24.7 - Prob. 39PTSCh. 24.7 - Prob. 40ATSCh. 24.7 - Prob. 41CCCh. 24 - Prob. 42PPCh. 24 - Prob. 43PPCh. 24 - Prob. 44PPCh. 24 - Prob. 45PPCh. 24 - Prob. 46PPCh. 24 - Prob. 47PPCh. 24 - Prob. 48PPCh. 24 - Prob. 49PPCh. 24 - Prob. 50PPCh. 24 - Prob. 51PPCh. 24 - Prob. 52PPCh. 24 - Prob. 53PPCh. 24 - Prob. 54PPCh. 24 - Prob. 55PPCh. 24 - Prob. 56PPCh. 24 - Prob. 57PPCh. 24 - Prob. 58PPCh. 24 - Prob. 59PPCh. 24 - Prob. 60PPCh. 24 - Prob. 61PPCh. 24 - Prob. 62PPCh. 24 - Prob. 63PPCh. 24 - Prob. 64PPCh. 24 - Prob. 65PPCh. 24 - Prob. 66PPCh. 24 - Prob. 67PPCh. 24 - Prob. 68PPCh. 24 - Prob. 69PPCh. 24 - Prob. 70PPCh. 24 - Prob. 71PPCh. 24 - Prob. 72PPCh. 24 - Prob. 73PPCh. 24 - Prob. 74PPCh. 24 - Prob. 75PPCh. 24 - Prob. 76PPCh. 24 - Prob. 77PPCh. 24 - Prob. 78PPCh. 24 - Prob. 79PPCh. 24 - Prob. 80PPCh. 24 - Prob. 81IPCh. 24 - Prob. 82IPCh. 24 - Prob. 83IPCh. 24 - Prob. 84IPCh. 24 - Prob. 85IPCh. 24 - Prob. 86IPCh. 24 - Prob. 87CPCh. 24 - Prob. 88CPCh. 24 - Prob. 89CP
Knowledge Booster
Similar questions
- Draw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore any inorganic byproducts. + Br CH3 Q Strong Base Drawing Atoms, Bonds and Rings Charges Undo Reset H "Br H N Br. Remove Done .N. Drag To Panarrow_forwardCurved arrows are used to illustrate the flow of electrons. Use the reaction conditions provided and follow the curved arrows to draw the product of this elementary step in an elimination mechanism. Include all lone pairs and charges as appropriate. Ignore stereochemistry. Ignore byproducts. + Br: .. 8 0.01 M NaOH heat Drawing Q Atoms, Bonds and Rings Charges and Lone Pairs Draw or tap a new bond to see suggestions. Undo Reset Remove Done + Drag To Panarrow_forward+ Draw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore any inorganic byproducts. Ph CH2CH3 H H3C H Br DBN [૪] Drawing Atoms, Bonds and Rings H | OH Charges ―00 H. C | Undo Reset Br I Remove Done Drag To Pan +arrow_forward
- Reaction A Now the production A ΠIn the product of reaction i 12 Dear the product of actionarrow_forwardMacmillan Learnin When an unknown amine reacts with an unknown acid chloride, an amide with a molecular mass of 163 g/mol (M* = 163 m/z) is formed. In the infrared spectrum, important absorptions appear at 1661, 750 and 690 cm-1. The 13C NMR and DEPT spectra are provided. Draw the structure of the product as the resonance contributor lacking any formal charges. 13C NMR DEPT 90 200 160 120 80 40 0 200 160 120 80 DEPT 135 200 160 120 80 40 0 Draw the unknown amide. 40 40 0arrow_forwardDraw the major product karmed when I reach with the epoxide. Use walge dah bonds, including hydrogen al alcach genic center, to show the chemistry of the product Beeldraw any hydrogen akams on coxygen where applicablearrow_forward
- Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. H I Select to Add Arrows + H H 'H Q H2O H2O CI:O .H H H H I Select to Add Arrows I : C H2O H H H Select to Add Arrows 'Harrow_forward+ Draw an alkyl halide that produces ONLY the following alkene in an E2 elimination. Ignore any inorganic byproducts. Drawing Strong Base Q Atoms, Bonds and Rings Charges HO Br H2N Undo Reset Remove Done Drag To Panarrow_forwardFor the dehydrohalogenation (E2) reaction shown, draw the major organic product. Хок Br tert-butanol heat Select Drew Templates More Erase CH QQQarrow_forward
- Macmillan Learning Draw the major, neutral organic product for each substitution reaction. For this question, assume that each substitution reaction goes to completion. Disregard elimination. Reaction A. CI H₂O Select Draw Templates More Erase C Harrow_forwardMacmillan Learning Reaction B: CI HO_ 곳으 / Select Draw Templates More с € H D Erasearrow_forwardWhen 2-bromo-93-dimethylbutane is heated with sodium methoxide, one majors.. në la formed. 4th attempt Part 1 (0.5 point) t Ji See Periodic Table See Hint Draw the major alkene product and all other byproducts. Be sure to include lone-pair electrons and charges. Part 2 (0.5 point) What type of mechanism is occuring? Choose one: AS1 3rd attempt X H 41 See Hint Part 1 (0.5 point) Feedback See Periodic Table See Hintarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage Learning
ChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill Education
Principles of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill Education
Chemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
Chemistry
Chemistry
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Cengage Learning
Chemistry
Chemistry
ISBN:9781259911156
Author:Raymond Chang Dr., Jason Overby Professor
Publisher:McGraw-Hill Education
Principles of Instrumental Analysis
Chemistry
ISBN:9781305577213
Author:Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9780078021558
Author:Janice Gorzynski Smith Dr.
Publisher:McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry
ISBN:9781305079373
Author:William L. Masterton, Cecile N. Hurley
Publisher:Cengage Learning
Elementary Principles of Chemical Processes, Bind...
Chemistry
ISBN:9781118431221
Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:WILEY