Concept explainers
(a)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
(b)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
(c)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
(d)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
(e)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
(f)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
(g)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
(h)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
(i)
To determine: The more acidic member in the given pair of isomer with an explanation.
Interpretation: The more acidic member in the given pair of isomer is to be stated and the reason for its selection is to be explained.
Concept introduction: When an acid donates a proton the species formed is known as conjugate base and when the base accepts a proton the species formed is known as conjugate acid. The acidity and basicity of a compound is influenced by the resonance. The amount of stability depends on the delocalization of the charge through the resonance.
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Chapter 2 Solutions
ORGANIC CHEMISTRY MASTERINGCHEM ACCESS
- a) Draw the conjugate base of the compound shown. Include all resonance structures. b) The pKa of phenol is 10. Does the compound shown have a pKa greater or less than 10? Fully explain your answer. (Hint: “It’s more acidic” or “it’s less acidic” is not a full explanation)arrow_forwardThe powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and whether there is a second carbonyl group attached to the a-carbon. Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is indicated in blue in each structure. Highest acidity Lowest acidity Answer Bank H CH3 H CH3 H. CH3 H3C CH3 H3C CH3 H. H. H3C. CH3 H. H 0-CH3arrow_forwardWhy is the N-H bond of an imide especially acidic? A) The conjugate acid is stabilized by resonance. B) The conjugate base is stabilized by resonance. The conjugate base is stabilized by (c) intramolecular hydrogen bonding. The conjugate base is stabilized by electron- (D donating inductive effect.arrow_forward
- 4. Arrange the compounds in the following set in order of increasing basicity (1-the most basic; 3-the least basic). Explain your answer! Magnesium hydroxide, magnesium acetate, methylmagnesium bromidearrow_forwardThe powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and whether there is a second carbonyl group attached to the a-carbon. Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is indicated in blue in each structure. Highest acidity Lowest acidity Answer Bank H. H. CH3 H. -CH CH3 H.C H. H3C CH3 H. H. CH H. H,C CH3 H. H. H. -CHarrow_forwardThe powerful electron-withdrawing property of a carbonyl group increases the acidity of a-protons (i.e., protons attached to a carbon that is adjacent to the carbonyl group). The effect varies depending on what else is attached to the carbonyl, and whether there is a second carbonyl group attached to the a-carbon. Rank the structures from highest acidity (lowest pK, value) to lowest acidity (highest pK, value). The acidic hydrogen is indicated in blue in each structure. Highest acidity Lowest acidity Answer Bank H;C, CH, H- CH, CH H3C CH3 H H. CH3 H3C H. CH3 CH3 Harrow_forward
- 9.) Explain why NaNH2 favors the enolate ion in the following reaction, but NaOH favors an equilibrium. (B: represents the base – either NANH, or NaOH). You'll need to consider acid/base strength (pKa values). B: + BH enolate ionarrow_forwardPut the following compounds in order from weakest acid to strongest acid. Explain (pKa values are not enough and trends should be considered).arrow_forwardDraw the major organic product of the Bronsted acid-base reaction. Include all lone pairs and charges as appropriate. Ignore any counterions. NaNHz :O: Harrow_forward
- The structure of ascorbic acid is shown below. Redraw the structure and circle the most acidic hydrogen. Briefly explain your selection.arrow_forwardRank the following in order of decreasing basicity and explain why (based on their structures). hydroxide ion, ethoxide ion, phenoxide ion, and carboxylate ionarrow_forwardAmides are weak nucleophiles but their conjugate bases are string nucleophiles. The amide drawn below can be deprotonated in four possible locations, labeled A-D but two are considerably more acidic than the others. Draw the two different Bronsted Lowery acid/base reactions (using HO- as the BL base) showing the deprotonation at these two locations. Draw all RS with arrows for both conjugate bases but no hybrids. Based on your resonance analysis which location is the most acidic in the molecule? Why is it most acidic? Amides can also be protonated by a strong acid in two different locations. Draw two different conjugate acids for the amide above as well as RS with arrows for each. Based on your resonance analysis which atom is the most basic in an amide?arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning