a) Draw all resonance forms of 3-hydroxybenzaldehyde and of the corresponding conjugate base. W hichconclusions can you draw for its acidity (pKa) in comparison to phenol?|b) Draw all resonance forms of 3-hydroxybenzaldehyde and of the corresponding conjugate base. Whichconclusions can you draw for its acidity (pKa) in comparison to phenol and 3-hydroxybenzaldehyde?c) Discuss the relative acidities of 2-hydroxybenzaldehyd und 4-hydroxybenzaldehyd.

The conjugate base can form an intramolecular hydrogen bond, which stabilizes the negative…

Answered: a) Draw all resonance forms of…

Organic Chemistry: A Guided Inquiry

2nd Edition

ISBN:9780618974122

Author:Andrei Straumanis

Publisher:Andrei Straumanis

Chapter20: Acidity And Pka Of Phenols

Section: Chapter Questions

Problem 20CTQ

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Phenol has a pka = 10.0. 4-Hydroxybenzaldehyde has a pka = 7.3. Draw resonance forms of the conjugate base of both and explain why 4-hydroxybenzaldehyde is more acidic. (Acidic H is underlined.) OH phenol OH -H* - H* 4-hyroxybenzaldehyde
Rank the labeled nitrogen atoms in each compound in order of increasing basicity. Histamine causes the runny nose and watery eyes associated with allergies, and trazodone is a drug used as a sedative and antidepressant.
Rank the given compounds in order of decreasing basicity. 1=most basic, 4=least basic
Rank the indicated a-H’s from most to least acidic (most acidic= 1). Be sure to explain your rankings for each by drawing significant resonance structures for the conjugate base and commenting on any other factors that contribute to your rankings.
h) Which is a weaker base and why? Pyridine Pyrrole i) Name the following compounds. H2N A B NH2
Rank the following compounds in order of increasing acidity (1 = least acidic, 3 = most acidic) and in the space provided use resonance (of the conjugate base) to explain why the compound you have labelled “3” is the most acidic.
Identify the most and the least acidic compound in each of the following sets. Leave the remaining answer in each set blank. a) 2,4-dinitrobenzoic acid: v p-nitrobenzoic acid: p-bromobenzoic acid: b) benzoic acid: v formic acid: v propanoic acid: c) cyclohexanol: v phenol: v benzoic acid:
Explain why m-nitroaniline is a stronger base than p-nitroaniline.
For each molecule below, draw the conjugate acid or conjugate base or both if the molecule hasboth a conjugate acid and a conjugate base (e.g., water).
Rank the following compounds in their correct order of acidity. 1=Most acidic and 4=least acidic.
Which compound is the strongest base?
Is p-methylphenol more acidic than phenol? Why or why not?

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