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
Want to see the full answer?
Check out a sample textbook solution
Chapter 14 Solutions
Organic Chemistry: Principles and Mechanisms (Second Edition)
- please provide the structure for this problem, thank you!arrow_forwardDraw the Fischer projection from the skeletal structure shown below. HO OH OH OH OH H Q Drawing Atoms, Bonds and Rings Charges I ☐ T HO H H OH HO I CH2OH H OH Drag H OH -CH2OH CHO -COOH Undo Reset Remove Donearrow_forwardplease provide the structure for this problem, thank youarrow_forward
- presented by Morallen Lig Intermine the hand product for the given mution by adding atoms, bonds, nonhonding diarion panda скуль Step 3: Comp the draw the product Step 2: Agama workup Compithe 429 ملولةarrow_forwardReaction A 0,0arrow_forwardpresented by Morillon Leaning Predict the organic product for the min кусур HSC Adithane carved arnown to come than that to the condon slchroruis in acid in in aquishri with ноюarrow_forward
- 6.15PM Sun Mar 30 K Draw the major product of this reaction. Include any relevant stereochemistry. Ignore inorganic byproducts. Problem 1 of O H [PhзPCH2CH3]*C|¯ NaH Drawing > Q Atoms, Bonds and Draw or tap a nearrow_forward8:17 PM Sun Mar 30 Draw the major product of this reaction. Ignore inorganic byproducts. HSCH2CH2CH2SH, BF3 Probler Drawing Ato Bonds Clarrow_forwardpresented by Mr L How the coprion. (Il Done in no wraction, dew the starting redential) доarrow_forward
- 8:16 PM Sun Mar 30 K Draw the major product of this reaction. Ignore inorganic byproducts. Proble 1. CH3MgBr 2. H3O+ F Drawingarrow_forwardо но оarrow_forwardName the major organic product of the following action of 4-chloro-4-methyl-1-pentanol in neutral pollution 10+ Now the product. The product has a molecular formula f b. In a singly hain, the starting, material again converts into a secule with the molecular kormula CIO. but with comply Draw the major organic structure inhalationarrow_forward
Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning