2. y-hydrogens in a,ß-unsaturated carbonyl compounds have a pKa similar to a-carbonyl hydrogens (~19) due to the stability of the conjugate base via resonance. Provide the conjugate base of the compound shown and draw two additional resonance structures of the conjugate base in the boxes provided. ОН H. a conjugate base Resonance structure 1 Resonance structure 2
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- References From each pair, select the stronger base. Then draw the conjugate acid of the stronger base below. CH30 or CH3COO- • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • You do not have to include lone pairs in your answer. C opy aste ChemDoodle archFrom each pair, select the stronger base. Then draw the conjugate acid of the stronger base below. CICH,CH,0¯ or CH;CH,0- • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • You do not have to include lone pairs in your answer. opy aste [FRank 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.
- Select the stronger base and then draw its conjugate acid below. CICH₂CH₂O or CH3CH₂O- • You do not have to consider stereochemistry. • You do not have to explicitly draw H atoms. • You do not have to include lone pairs in your answer. Ⓡ OO. n[1] ? ChemDoodle10. Rank the following in order of acidity of their -OH group (1-4: 1 for strongest) Explain the reasoning for your answr. Do not say" because of their pKa values!" You need to use ARIO and solvation to explain the reason underlying their relative_pKa values 10.a он OH он он CI 10b. ОН ОН OH OHRank 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.
- 4 5 Arrange the following bases in increasing base strength. There is no partial credit on this problem. Weakest base 1 2 3 Pyridine (C5H5N), Kb = 1.7 x 10-⁹ Aniline (C6H5NH2), Kb = 3.9 x 10-10 Strongest base Methylamine (CH3NH₂), Kb = 4.4 x 10-4 Hydrazine (N2H4), Kb = 1.3 x 10-6 ⠀ Dimethylamine ((CH3)2NH), K₂ = 5.1 x 10-4Answer questions a-c about the Bronsted acid-base reaction below using the Q41 identifying letters A-D below each structure. A table of pk, values for various organic and inorganic acids can be found in the references section. NH₂ A amide B ethyl acetate CH₂ NH3 C ammonial + I CH₂ D ethyl acetate enolate a) The weaker acid is b) Its conjugate base is c) The species that predominate at equilibrium are (two letters, e.g. AC)6) Assign a given pka to the following compounds. CF3 F₂C OH → он NH₂ H₂Se CF₂ 7) In class we talked about the concept of pKH, which is the pK₂ of the protonated version of the noted molecule. Assign a given pkan to the following molecules. Two of the molecules are so similar it would hard to predict their relative pKan values from structure alone. 9) Circle the most acidic species below. OH NH₂ 8] Circle the weakest base from along the compounds below. H₂S ново F₂C OH O NH pk₂ 5.4 9.3 12.9 15.9 H₂O РКан -10 9.2 10.7 10.8
- solvent such as hydrocarbon, neither accept nor donate protons.Rank the labeled protons (Ha–Hc) in mandelic acid, a naturally occurring carboxylic acid in plums and peaches, in order of increasing acidity. Explain in detail why you chose this order.Which is a stronger acid and has the most stable conjugate base? Estimate the pKA values for both compounds.