Concept explainers
(a)
Interpretation: Which one of the given pair of molecules should have the more acidic
Concept introduction:
The strength of an acid depends on the stability of the conjugate base formed by the removal of the proton. The higher the stability of the conjugate base, the stronger the acid.
The stability of the conjugate base depends on several factors, the electronegativity of the atom that bears the negative charge, possible delocalization of the charge because of resonance, and the hybridization of the atom that bears the charge.
If the electronegativity and hybridization are similar, the resonance stabilization of the charge determines the stability of the conjugate base. The more the number of atoms over which the charge is delocalized, the higher the stability of the conjugate base, and hence the higher the strength of the acid. Aromaticity also plays a role in stabilization. The order of stability of cyclic conjugate bases with double bonds is
(b)
Interpretation: Which one of the given pair of molecules should have the more acidic
Concept introduction:
The strength of an acid depends on the stability of the conjugate base formed by the removal of the proton. The higher the stability of the conjugate base, the stronger the acid.
The stability of the conjugate base depends on several factors, the electronegativity of the atom that bears the negative charge, possible delocalization of the charge because of resonance, and the hybridization of the atom that bears the charge.
If the electronegativity and hybridization are similar, the resonance stabilization of the charge determines the stability of the conjugate base. The more the number of atoms over which the charge is delocalized, the higher the stability of the conjugate base, and hence the higher the strength of the acid. Aromaticity also plays a role in stabilization. The order of stability of cyclic conjugate bases with double bonds is
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Chapter 14 Solutions
ORGANIC CHEMISTRY SG/SM PA +SQUARECAP E
- Curved arrows are used to illustrate the flow of electrons. Using the provided resonance structures, draw the curved electron- pushing arrows to show the interconversion between resonance hybrid contributors. Be sure to account for all bond- breaking and bond-making steps. I I I I :O: farrow_forwardWhich one is more acidic? Why?arrow_forwardIf a carbocation is present, do you typically push electrons towards or away from it? Why? Do you generally push electrons towards or away from a negative charge? Why? In a neutral molecule, should you push pi electrons towards the more or less electronegative atom? Why?arrow_forward
- ew topic [References Draw both resonance structures of the anion formed by the reaction of the most acidic C-H bond of the compound below with base. H3C SCH3 • Include all valence lone pairs in your answer. • For structures having different hydrogens of comparable acidity, assume that the reaction occurs at the less- substituted carbon. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate resonance structures using the → symbol from the drop-down menu. C P opy aste 11:58 M 18 52% 4/11/2021arrow_forwardH Select to Add Arrows H H H H H Li Ⓒ Li Ⓒ Problem 3 of 21 Please select a drawing or reagent frarrow_forwardConsider the below molecule and its hydrogen atoms labeled a through e. Rank the named hydrogen atoms in order of increasing acidity. Explain your choice.arrow_forward
- Which arrow (x, y, or z) points toward the most acidic proton in the molecule to the right? (Arrows pointing toward C can be assumed to point at the H attached to that C.) Which structural feature plays the most significant role in influencing the relative acidities of the indicated protons? a. inductive effect b. size c. resonance d. hybridizationarrow_forwardIn the picture, Each of the following compounds has more than one kind of (a-H's). First draw all a-H in, and circle the ones that are more acidic (that is, the ones more likely removed with a suitable base) in each compound. Thank you!arrow_forwardSection A. Check your understanding +H' H-H 1. Explain why a carbonyl C=O bond is protonated at the lone pair while and alkene C-C bond is protonated at the pi bond. Use a MO diagram to justify your answer. &-C-Harrow_forward
- Acidity in H structures. Which is the most acidic? Arrange in order of increasing acidity with short explanation of how. note: the Hs are bonded to Carbons.arrow_forwardWhy does Hammett Equation only apply to meta and para substituted rings and not others? Explainarrow_forward3. For the following set of compounds, box the most basic and circle the least basic.arrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning