Organic ChemistryMain MenuLecture 1: Introduction to Molecular OrbitalsLecture 10: Intermolecular Forces and Intro to ReactivityLecture 11: Alkenes as Nucleophiles ILectures 12 and 13: Alkenes II & IIILecture 14: Benzenes as Nucleophiles ILecture 15 objectives and skillsLecture 2: Molecular Orbitals in Organic StructuresLecture 3: Molecular Orbitals and ResonanceLecture 4: Molecular Orbitals and AromaticityLecture 5: Nomenclature and IR SpectroscopyLecture 6: Stereochemistry ILecture 7: Stereochemistry IILecture 8: Newman and Fisher ProjectionsLecture 9: Conformations and Cyclohexane RingsJulio Terra2fb22914f73f9e5a767bf7fb83987dca0e153e4a
SOLUTION 10.3c
12020-03-01T15:12:21-08:00Julio Terra2fb22914f73f9e5a767bf7fb83987dca0e153e4a359921plain2020-03-01T15:12:21-08:00Julio Terra2fb22914f73f9e5a767bf7fb83987dca0e153e4aCarboxylic acids and phenols both have resonance stabilization of their conjugate bases, which makes them stronger acids than aliphatic alcohols. Carboxylate salts have equal distribution of anionic charge across both oxygens. This makes the anion more stabilized (weaker base), thus the acid is the stronger acid as compared to phenol. In phenols, there are more resonance structures, but they are not all equal. The contributor with aromatic ring and localized oxygen anion is the best contributor, so charge is less equally delocalized than in a carboxylic acid. Between the two carboxylic acids, the one with the fluorine has the strongest inductive EWG effects, which helps stabilize the anionic conjugate base (or polarize the acidic OH).
Describe the intermolecular forces, in decreasing significance. SOLUTION
H2CO
CH3CH2OH
CH3CON(CH3)2
CH3C≡CH
Predict which compound, for each set, would have the strongest intermolecular forces. SOLUTION
CH3CH2CH2CH3, (CH3)2CHCH3, (CH3)4C
CH3CH2CH2OH, (CH3)2COHCH3, (CH3)3COH
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you're good, move to the next problem ;)
Problem 10.2: Physical Properties
Predict which compound, for each set, will have the highest boiling point. SOLUTION
CH3CH2CH3, CH3CH2CH2OH, CH3OCH2CH3
CH3CH2CH2CH2OH, (CH3) 2CHCH2OH, (CH3) 3COH
CH3CH3, CH3CF3, CF3CF3
HN(CH3) 2, H2N(CH3), H3N
Why does salt (NaCl) dissolve in water? SOLUTION
Why does salt (NaCl) NOT dissolve in hexane? SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you're good, move to the problem below ;)
Problem 10.3: Acids-Bases
Identify the conjugate acid and conjugate base in each of the following pairs of compounds. Draw the Lewis structures of each species and add necessary formal charges. SOLUTION
[(CH3)2CHO]- and (CH3)2CHOH
HNO3 and [NO3]-
[NH2]- and NH3
Identify each of the following as Lewis acid or Lewis base: [(CH3)3C]+, BH3, [CH3]-, and [HO]-. SOLUTION
Rank the following from least acidic to most acidic. SOLUTION
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Problem 10.4: Mechanisms
Add the curved arrows to complete each transformation below. SOLUTION
Find the error in each mechanism below. Propose a corrected mechanism. SOLUTION
If you made some mistakes or want to practice more, review the concepts that gave you trouble and work on this extra problem. If you're good, move to the next lecture ;)
