Answered: Propose mechanisms to show the…

Science

Chemistry

Propose mechanisms to show the interchange of protons between ethanol molecules under b) base catalysis

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter18: Functional Derivatives Of Carboxylic Acids

Section: Chapter Questions

Problem 18.43P: The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas...

See similar textbooks

Similar questions

Phenol (hydroxybenzene) behaves as a weak acid. a) Write out the equilibrium equation for its partial dissociation in water. b) Write out the expression for the acid dissociation constant, Ka. d) Draw the conjugate base of phenol and show how it is stabilised by resonance. e) Compare and explain the acidity of phenol (p = 9.9) with that of: cyclohexanol (pk = 16.0) 3-fluorophenol (pK₁ = 9.3) 4-acetylphenol (pK, = 8.1)
Using curved arrows to show movement of electron pairs, show the mechanism for this reaction. It is only necessary to draw one resonance structure for any intermediates that are resonance hybrids. Note that the H atom of the hydroxyl group is acidic enough to be removed by OH–; the first step in the mechanism is a proton transfer. The general mechanism for base-mediated saponification of an ester is outlined in one of the discussion videos that has been posted for this experiment.
Alcohols are acidic in nature. Therefore, a strong base can abstract the acidic hydrogen atom of the alcohol in a process known as deprotonation. The alcohol forms an alkoxide ion by losing the proton attached to the oxygen atom of the hydroxyl ( -OH) group. The alkoxide formed can act as a base or a nucleophile depending on the substrate and reaction conditions. However, not all bases can abstract the acidic proton of alcohols and not all alcohols easily lose the proton. Deprotonation depends on the strength of the base and the acidity of the alcohol. Strong bases, such as NaNH2, can easily abstract a proton from almost all alcohols. Likewise, more acidic alcohols lose a proton more easily. Determine which of the following reactions would undergo deprotonation based on the strength of the base and the acidity of the alcohol. Check all that apply. ► View Available Hint(s) CH3CH,OH + NH3 →CH,CH,O-NH CH3 CH3 H3C-C-H+NH3 → H3 C-C-H OH O-NH CH3CH2OH + NaNH, → CH3CH,O-Na* + NH3 CHC12 Cl₂…
Industrial chemistry: Provide a mechanism for the hydrocracking of n-Heptane in the presence of hydrogen gas to isopentane and ethane.
The following sequence of steps converts (R)-2-octanol to (S)-2-octanol. Propose structural formulas for intermediates A and B, specify the configuration of each, and account for the inversion of configuration in this sequence.
4. The pk, of vanillin is about 9, which is much more acidic than a normal alcohol. Draw a reaction showing the deprotonation of vanillin with NaOH, and then draw six resonance structures of the conjugate base. Draw the hybrid structure and clearly indicate how the negative charge is distributed in the compound.
Waste vegetable oil (WVO; e. g. spent deep fryer oil) is often used to produce biodiesel. WVO tends to have relatively high amounts of free fatty acids (FFA) compared to unused vegetable oil. For a base catalyzed process, why might the presence of FFA cause problems? Provide a reaction scheme in your explanation.
b) 4. Rank the indicated protons in each of the given structures in order of decreasing acidity. Show the details for how you arrived at the answer. SHa HbN & OHC
1. Rank the following molecules in terms of increasing acidity. Explain your rankings in terms of stability of the corresponding conjugate base. OH HO, SH NaNH2 =H HO,
According to the Evan's pKa table, phenol has a pKa of 9.95. p-Nitro and m-nitrophenol have pKas of 7.14 and 8.35 respectively. Using resonance structures, explain the observed trends in the acidity of these molecules.
Compare and explain the acidity of phenol, ethanol, acetic acid. (Using pKa, structures of conjugate base)
11.27: Tell which is the stronger base and why? Aniline or p-cyanoaniline b) aniline or diphenylamine WH₂ |ال 11.30: Place the following substances, which have nearly identical formula weights, in order of increasing boiling point? 1-aminobutane, 1-butanol, methyl propyl ether, pentane