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Chemistry 20 Acid-Base Reactions Guide

1. The document provides a chemistry handout with questions about acid-base reactions, molecular orbital diagrams, and reaction mechanisms. Students are asked to determine relative acidities, calculate equilibrium constants, explain differences in base strength, draw molecular orbital diagrams, and use curved arrows to show reaction steps and identify orbitals involved.

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5 views3 pages

Chemistry 20 Acid-Base Reactions Guide

1. The document provides a chemistry handout with questions about acid-base reactions, molecular orbital diagrams, and reaction mechanisms. Students are asked to determine relative acidities, calculate equilibrium constants, explain differences in base strength, draw molecular orbital diagrams, and use curved arrows to show reaction steps and identify orbitals involved.

Uploaded by

Đạt Lê
Copyright
© All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
Available Formats
Download as PDF, TXT or read online on Scribd

Chemistry 20 Section Handout: Module 2 Spring 2016

1. In each of the following molecules, determine which of the shown protons is more acidic. Explain your
reasoning in one sentence.

O
N
(a) SH (b) (c) N
HO
H H H
O
H

O O

(d) OH (e) O
HO N H
Br O H

2. Using your knowledge of pKa values, calculate the equilibrium constant for the following acid-base reaction.

OH Keq = ? O
(a)
+ HS + H2S

3. For each pair of bases, briefly explain why the base on the left is stronger than the base on the right.

(a) O O

N O
stronger base
O

O O
(b)
H3C NH2 H3C CH3

stronger base
Chemistry 20 Section Handout: Module 2 Spring 2016

4. Consider the following two species:

O
A: H C C B:

(a) For each species, provide a complete molecular orbital diagram showing the energies of all the orbitals in
the molecule. Label each orbital with an appropriate label ( , *, , *, or n), and fill in each orbital with the
appropriate number of electrons. Identify the HOMO and LUMO of each molecule by labeling them on the
diagram.

(b) When these two molecules react, the HOMO of one molecule will react with the LUMO of the other. Identify
which HOMO will react with which LUMO.

(c) Provide the curved arrows for this single-step reaction, and draw the product that would result.

5. The following species react in a two-step reaction. For each step:

(a) Identify the HOMO and LUMO of each species.


(b) Determine which species will be the nucleophile and which will be the electrophile.
(c) Show how the species would react using curved arrows
(d) Predict the product.

Step 1 Step 2
+ H Cl
Chemistry 20 Section Handout: Module 2 Spring 2016

6. Based on the structures given, draw curved arrows to account for each step of the following reactions. Be
aware that you may need to draw in lone pairs if they are not shown. Also identify the donor and acceptor
orbitals for each step of the reaction.

H
O H OH O
O + H OH
+ O
H

Donor:
Donor:
Acceptor:
Acceptor:

HO
HO OH
H HO H O O H
+ O
O O H
H OH

Donor: Donor:

Acceptor: Acceptor:

H
HO O
OH + O O
HO H OH

Donor:
Donor:
Acceptor:
Acceptor:

H
O O + O O O
H
H OH HO
OH

Donor:

Acceptor:

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