Н Н Н нн H ро нн H Figure 4: Organic Bronsted acids нн 0

Chemistry
10th Edition
ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Criteria for success
All molecular drawings must be valid Lewis structures (octet rule, formal charge, valence, geometry). Curved arrows
will be interpreted very strictly: Thus, they must clearly indicate the origin and destination of electron delocalization.
Explanations ought to be logical and complete. If electron delocalization (resonance) is used as part of the explanation, res-
onance structures must be drawn to demonstrate the context in which delocalization applies.
Tasks
Select two compounds of the three shown in Fig. 4 by labeling them as X and Y (the most acidic hydrogens are high-
lighted). Of the two compounds you selected:
1. Explain which is stronger, and which is weaker Brønsted-Lowry acid? Use chemical drawing and no more than 4
sentences.
2. Draw an acid-base reaction of one of the compounds in Fig. 4 (your choice) with sodium amide (Na NH₂).
Show curved arrows. Label acid, base, conjugate acid and conjugate base.
chose? Explain.
3. Is this base (Na*NH₂) strong enough base to fully deprotonate the acid you
Note: Full detrotonation = over 95% of product at equilibrium (95:5 product to substrate mole ratio).
HH
H
HH
H
HH
H
Figure 4: Organic Brønsted acids
HH
x
O
O
Transcribed Image Text:Criteria for success All molecular drawings must be valid Lewis structures (octet rule, formal charge, valence, geometry). Curved arrows will be interpreted very strictly: Thus, they must clearly indicate the origin and destination of electron delocalization. Explanations ought to be logical and complete. If electron delocalization (resonance) is used as part of the explanation, res- onance structures must be drawn to demonstrate the context in which delocalization applies. Tasks Select two compounds of the three shown in Fig. 4 by labeling them as X and Y (the most acidic hydrogens are high- lighted). Of the two compounds you selected: 1. Explain which is stronger, and which is weaker Brønsted-Lowry acid? Use chemical drawing and no more than 4 sentences. 2. Draw an acid-base reaction of one of the compounds in Fig. 4 (your choice) with sodium amide (Na NH₂). Show curved arrows. Label acid, base, conjugate acid and conjugate base. chose? Explain. 3. Is this base (Na*NH₂) strong enough base to fully deprotonate the acid you Note: Full detrotonation = over 95% of product at equilibrium (95:5 product to substrate mole ratio). HH H HH H HH H Figure 4: Organic Brønsted acids HH x O O
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