a) Acetic acid, oxalic acid, formic acid
Interpretation:
Acetic acid, oxalic acid and formic acid are to be arranged in the increasing order of their acidity.
Concept introduction:
Any electron withdrawing group present in the acid increases the acidity of the acid while any electron releasing group present in the acid decreases the acidity. Inductive effect decreases with increasing distance of the substituent from the functional group.
To arrange:
Acetic acid, oxalic acid and formic acid in the increasing order of their acidity.
b) p-Bromobenzoic acid, p-nitrobenzoic acid, 2,4-dinitrobenzoic acid
Interpretation:
p-Bromobenzoic acid, p-nitrobenzoic acid and 2,4-dinitrobenzoic acid are to be arranged in the increasing order of their acidity.
Concept introduction:
Any electron withdrawing group present in the acid increases the acidity of the acid while any electron releasing group present in the acid decreases the acidity. Inductive effect decreases with increasing distance of the substituent from the functional group.
To arrange:
p-Bromobenzoic acid, p-nitrobenzoic acid and 2,4-dinitrobenzoic acid are to be arranged in the increasing order of their acidity.
c) Fluoroacetic acid, 3-fluoropropanoic acid, iodoacetic acid
Interpretation:
Fluoroacetic acid, 3-fluoropropanoic acid and iodoacetic acid are to be arranged in the increasing order of their acidity.
Concept introduction:
Any electron withdrawing group present in the acid increases the acidity of the acid while any electron releasing group present in the acid decreases the acidity. Inductive effect decreases with increasing distance of the substituent from the functional group.
To arrange:
Fluoroacetic acid, 3-fluoropropanoic acid and iodoacetic acid in the increasing order of their acidity.
Trending nowThis is a popular solution!
Chapter 20 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
- The preceding equation for the protonation of acetamide shows a hypothetical product that is not actually formed. When acetamide is protonated by a strong enough acid, it does not protonate on nitrogen, but at a different basic site. Draw the structure of the actual conjugate acid of acetamide, and explain (resonance) why protonation occurs where it does rather than on nitrogen. Calculate the pKa of this conjugate acid.arrow_forwardWrite the equilibrium-constant expressions and obtainnumerical values for each constant in. (a) the basic dissociation of aniline, C6H5NH2. (b) the acidic dissociation of hypochlorous acid,HClO. (c) the acidic dissociation of methyl ammoniumhydrochloride, CH3NH3Cl. (d) the basic dissociation of NaNO2. (e) the dissociation of H3AsO3to H3O+and AsO33-. (f) the reaction of C2O42-with H2O to give H2C2O4and OH-. show solutionarrow_forwardThe hydrolysis of the ester shown here is catalyzed by morpholine. Explain how morpholine catalyzes the reaction. (Hint: The pKa of the conjugateacid of morpholine is 9.3, so morpholine is too weak a base to function as a base catalyst.)arrow_forward
- p-Nitrobenzyl alcohol is more acidic than benzyl alcohol but p-Methoxybenzyl alcohol is less acidic. Illustrate your explanation.arrow_forwardHypoglycin A, an amino acid derivative found in unripened lychee, is anacutely toxic compound that produces seizures, coma, and sometimesdeath in undernourished children when ingested on an empty stomach. (a) Draw the neutral, positively charged, and negatively charged forms of hypoglycin A. (b) Which form predominates at pH = 1, 6, and 11? (c) What is the structure of hypoclycin A at its isoelectric point?arrow_forward1. Arrange the test samples in order of increasing reactivity with sodium bicarbonate? Explain briefly -Ethanoic acid, Butanoic acid, Benzoic acid 2. Arrange the test samples in order of increasing solubility in water? Explain briefly. -Ethylamine, Diethylamine, Aniline 3. Arrange the test samples in order of increasing basicity? Explain briefly. -NaOH, Ethylamine, Anilinearrow_forward
- Which has a lower pKa value, the conjugate acid of 3-bromoquinuclidine or the conjugate acid of 3 -chloroquinuclidine?arrow_forwardArrange the following molecules in increasing order of acidity. Base it only on their structural differences and explain how it is so. 1. Butanoic acid, Propionic acid, Propylamine, Butanearrow_forwardGive the expected organic product when phenylacetic acid, PhCH2COOH, is treated with reagent Q.)LiAlH4 followed by H2Oarrow_forward
- Explain this statement: Although 2-methoxyacetic acid (CH3OCH2COOH)is a stronger acid than acetic acid (CH3COOH), p-methoxybenzoic acid(CH3OC6H4COOH) is a weaker acid than benzoic acid (C6H5COOH).arrow_forward1. Arrange the following compounds in order of increasing acidity and explain the reason for the arrangement: Ethanoic acid, Butanoic Acid, Benzoic Acid, Salicyclic acid. 2. Arrange the test samples in order of increasing reactivity with sodium bicarbonate? Explain briefly. -Ethanoic acid, Butanoic acid, Benzoic acidarrow_forwardIndicate the order of basicity of: aniline, 2-propylamine and 1-(2-aminophenyl)ethanone. Explain.arrow_forward
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning