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. (15 points) Draw an appropriate mechanism for the following reaction.
H
N.
H*
+ H₂O
Draw a tripeptide of your choosing at pH 7. Have the N-terminus on the left and the C-terminus on the right. Then:
Draw a triangle around the α-carbons.
Draw a box around the R-groups.
Circle the atoms capable of hydrogen bonding.
Highlight the atoms involved in the formation of the peptide bonds.
What type of structure have you drawn? (primary, secondary, tertiary or quaternary protein structure). make sure its a tripeptide
Don't used hand raiting and don't used Ai solution
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
- Don't used hand raiting and don't used Ai solutionarrow_forwardDon't used Ai solution and don't used hand raitingarrow_forward> Organic Functional Groups Naming and drawing alkyl halides structure CI Br CI CI Explanation Check 2 name 1-chloro-2,4,9-trimethylnonane CI 2-iodo-2,3-dimethylbutane FEB 19 € E M tv MacBook Airarrow_forward
- Can you please explain to me this problem im very confused and lost. Help me step by step and in detail im soo lost.arrow_forward2) There are many forms of cancer, all of which involve abnormal cell growth. The growth and production of cells, called cell proliferation, is known to involve an enzyme called protein farnesyltransferase (PFTase). It is thought that inhibitors pf PFTase may be useful as anticancer drugs. The following molecule showed moderate activity as a potential PFTase inhibitor. Draw all stereoisomers of this compound. HO OHarrow_forwardConsidering rotation around the bond highlighted in red, draw the Newman projection for the most stable and least stable conformations when viewed down the red bond in the direction of the arrow. Part 1 of 2 H₁₂C H H Draw the Newman projection for the most stable conformation. Select a template to begin. Part 2 of 2 Draw the Newman projection for the least stable conformation. G 心arrow_forward
- personality of each of them in terms of nucleophile vs. electrophile (some can be considered acids/bases but we are not looking at that here). Note you may have to use your growing intuition to figure out the personality of one of the molecules below but I believe in you! Rationalize it out based on what we have called strong versus weak electrophiles in past mechanisms. Consider using the memes below to help guide your understanding! A OH O B CH3 C Molecule A: [Select] Molecule B: [Select] Molecule C: [Select] Molecule D: [Select] > H D OHarrow_forward4) Which oxygen atom in the structure below is most basic / nucleophilic? Please explain by discussing the electron density around each oxygen atom. Show at least three resonance structures for the compound. оогоarrow_forwardCan you show me this problem. Turn them into lewis dot structures for me please and then answer the question because I cant seem to comprehend it/ The diagrams on the picture look too small I guess.arrow_forward
- The fire releases 2.80 x 107 Joules of heat energy for each liter of oil burned. The water starts out at 24.5 °C, raising the water's temperature up to 100 °C, and then raises the temperature of the resulting steam up to 325 °C. How many liters of water will be needed to absorb the heat from the fire in this way, for each 1.0 liter of crude oil burned? 4186 J/(kg°C) = heat of water 2020 J/(kg°C) = heat of steam 2,256,000 (i.e. 2.256 x 106) J/kg = latent heat of vaporization for water (at the boiling point of 100 °C).arrow_forward6 Which of the following are likely to be significant resonance structures of a resonance hybrid? Draw another resonance structure for each of the compounds you select as being a resonance form. (A Br: Br: A B C D Earrow_forwardWrite the systematic (IUPAC) name for the following organic molecules. Note for advanced students: you do not need to include any E or Z prefixes in your names. Br structure Br Br Oweuarrow_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