Organic Chemistry Study Guide and Solutions
6th Edition
ISBN: 9781936221868
Author: Marc Loudon, Jim Parise
Publisher: W. H. Freeman
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 24, Problem 24.51AP
Interpretation Introduction
Interpretation:
The structure of missing compounds present in Wohl degradation reaction is to be stated. The curved-arrow mechanism for conversion of B to C and C to arabinose in the Wohl degradation reaction is to be shown.
Concept Introduction:
Wohl degradation is the reaction to convert aldose into other aldose with one carbon less. It is a chain contraction reaction of aldoses. The oxime of aldose is formed by reacting it with hydroxylamine and sodium methoxide. Then oxime will react with acetic anhydride in acetic acid and sodium acetate toform nitrile derivative. In the last step, the reaction with sodium methoxide in methanol results in removal of all acetate group and nitrile group toform aldose with one carbon lesser and sodium cyanide as by product.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
2. Draw the remaining two resonance structures for the carbocation intermediate in the
meta nitration of methyl benzoate AND explain why the meta orientation is preferred.
Hint: how is the placement of the cation favorable after addition of nitronium relative to
the electron withdrawing group? (2 pts)
H NO2
CO₂Me
Label all absorptions over 1500 cm-1. Please be specific and mark IR if needed for explanation.
Compound
OH
sp^3 C-H
C=O
C-O
Triglyceride
Identify the intermediate that is INITIALLY formed in a saponification reaction
(hydrolysis of an ester).
III
-OH
H₂O
HO OH
HO O
||
A
B
C
III
D
IV
IV
Chapter 24 Solutions
Organic Chemistry Study Guide and Solutions
Ch. 24 - Prob. 24.1PCh. 24 - Prob. 24.2PCh. 24 - Prob. 24.3PCh. 24 - Prob. 24.4PCh. 24 - Prob. 24.5PCh. 24 - Prob. 24.6PCh. 24 - Prob. 24.7PCh. 24 - Prob. 24.8PCh. 24 - Prob. 24.9PCh. 24 - Prob. 24.10P
Ch. 24 - Prob. 24.11PCh. 24 - Prob. 24.12PCh. 24 - Prob. 24.13PCh. 24 - Prob. 24.14PCh. 24 - Prob. 24.15PCh. 24 - Prob. 24.16PCh. 24 - Prob. 24.17PCh. 24 - Prob. 24.18PCh. 24 - Prob. 24.19PCh. 24 - Prob. 24.20PCh. 24 - Prob. 24.21PCh. 24 - Prob. 24.22PCh. 24 - Prob. 24.23PCh. 24 - Prob. 24.24PCh. 24 - Prob. 24.25PCh. 24 - Prob. 24.26PCh. 24 - Prob. 24.27PCh. 24 - Prob. 24.28PCh. 24 - Prob. 24.29PCh. 24 - Prob. 24.30PCh. 24 - Prob. 24.31PCh. 24 - Prob. 24.32PCh. 24 - Prob. 24.33PCh. 24 - Prob. 24.34APCh. 24 - Prob. 24.35APCh. 24 - Prob. 24.36APCh. 24 - Prob. 24.37APCh. 24 - Prob. 24.38APCh. 24 - Prob. 24.39APCh. 24 - Prob. 24.40APCh. 24 - Prob. 24.41APCh. 24 - Prob. 24.42APCh. 24 - Prob. 24.43APCh. 24 - Prob. 24.44APCh. 24 - Prob. 24.45APCh. 24 - Prob. 24.46APCh. 24 - Prob. 24.47APCh. 24 - Prob. 24.49APCh. 24 - Prob. 24.50APCh. 24 - Prob. 24.51APCh. 24 - Prob. 24.52APCh. 24 - Prob. 24.53APCh. 24 - Prob. 24.54APCh. 24 - Prob. 24.55APCh. 24 - Prob. 24.56APCh. 24 - Prob. 24.57APCh. 24 - Prob. 24.58APCh. 24 - Prob. 24.59APCh. 24 - Prob. 24.60APCh. 24 - Prob. 24.61APCh. 24 - Prob. 24.62AP
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
- Help me answer this practice sheet I found for an answer guidearrow_forwardshow the retrosynthesis of this molecule step by step starting with 1,3-dimethoxy benzene H3CO OH OH OCH 3arrow_forwardConsider the reaction of a propanoate ester with hydroxide ion shown below. A series of four alcohol leaving groups were tested to determine which would be the best leaving group. Based on the pKa values of the alcohols, predict which alcohol would produce the fastest hydrolysis reaction. HO FOR A Alcohol I, pKa =16.0 B Alcohol II, pKa =10.0 C Alcohol III, pKa = 7.2 + ROH D Alcohol IV, pKa = 6.6arrow_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. :0: NaOH, H₂O 00:4 Na O heat NaO Select to Add Arrows Select to Add Arrows :0: Na a NaOH, H2O :0: NaOH, H2O heat heat Na ONH Select to Add Arrowsarrow_forwardCurved 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 CH3NH3+ :0: :0: HO CH3NH2 HH iSelect to Add Arrows i Select to Add Arrows i HH CH3NH3+ CH3NH2 Select to Add Arrows i CH3NH3 CH3NH2 ايكدا HH Select to Add Arrowsarrow_forwardThe reaction is carried out with gases: A → B + C at 300 K. The total pressure is measured as a function of time (table). If the reaction order is 2, calculate the rate or kinetic constant k (in mol-1 L s¹) Ptotal (atm) 492 676 760 808 861 t(s) 0 600 1200 1800 3000arrow_forward
- can someone give a description of this NMR including whether its a triplt singlet doublet where the peak is around at ppm and what functional group it representsarrow_forward1. Determine the relationship between the following molecules as identical, diastereomers, or enantiomers (6 points, 2 points each). OH OH OH A-A OH HOT HO- ACHN and HO- ACHN OH HO HO ° OH and OH OH SH and ...SHarrow_forward20,0 Complete the electron pushing mechanism to y drawing the necomery unicaciones and carved on for Step 1: Add curved arms for the tint step, traiment with NalilĻ. The Nation 458 Step 2: Added for the second step, inalment with), how the "counterion bar Step 3: Daw the products of the last simplom organic and one incoganic spacient, including all nonbondingarrow_forward
- please provide the structure for this problem, thank you!arrow_forwardDraw the Fischer projection from the skeletal structure shown below. HO OH OH OH OH H Q Drawing Atoms, Bonds and Rings Charges I ☐ T HO H H OH HO I CH2OH H OH Drag H OH -CH2OH CHO -COOH Undo Reset Remove Donearrow_forwardplease provide the structure for this problem, thank youarrow_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: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning