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T A. Identify each chemical as either an “acid” or a “base” in the following reactions, and
identify “conjugate” relationships.
-You should have one acid and one base on each side
-You should have two conjugate pairs
+ H2O + CH3OH2+
4. CH3OH + H3O
NH O
8.
NHNa ONa
9.
10. Ph O Ph O
NHNa NHNa
11. O
T C. Rank the basicity of the following sets: Multiple Variable Problems
13. O O OH
ONa
ONa NHNa OH
14. O
O
O NH OH
15. O
T
D. Choose the More Acidic for Each of the Following Pairs: Single Variable Problems
NH3 NH4
16.
17. OH2 OH
OH NH2 CH3
18.
NH2
19. OH
OH
20. OH
NH2 NH2
21.
E. Rank the acidity of the following sets: Multiple Variable Problems
T OH OH2 OH
HF
22. O O
NH3 OH
NH2
H2O
23. O O
OH OH NH2
24. O
O
25. O
OH
T HeO OH NH2
26. O
F. Draw arrow to show whether equilibrium favors products or reactants. (Why?) Keys:
O O
1. Charge
H2O + 2. Elecronegativity
OH +
27. H OH H O 3. Resonance
OH + NH O + NH2
28.
Acidity/Basicity Table
T Acid Base Base
Entry Class Structure Ka Strength Base Strength Stability
3 Carboxylic O 10-5 O
Acid
R OH R O
4 Ammonium 10-12 R
R H
Ion (Charged) N N
R R R R
Charged, but only Neutral, but basic!
weakly acidic!
• The above three factors will be needed this semester. The following three will also
become important in Organic II.
4. Hybridization
5. Impact of Electron Donors/Withdrawers
6. Amines/Ammoniums
Chem 341 Jasperse Ch. 1 Structure + Intro 13
• Anion Stability
• Basicity
• Electronegativity