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Tutorial 1

This document contains 5 questions about organic synthesis, mechanisms, structure, bonding, resonance and acid-base theories: 1. Determine the formal charges for atoms marked with asterisks in given compounds. 2. Identify the most acidic hydrogen in given compounds. 3. Use a provided pKa table to order compounds by acidity and basicity, and predict species at equilibrium when compounds are mixed. 4. Identify which pairs of structures represent resonance structures. 5. Indicate which structure is the more stable resonance contributor for identified resonance structure pairs.

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94 views3 pages

Tutorial 1

This document contains 5 questions about organic synthesis, mechanisms, structure, bonding, resonance and acid-base theories: 1. Determine the formal charges for atoms marked with asterisks in given compounds. 2. Identify the most acidic hydrogen in given compounds. 3. Use a provided pKa table to order compounds by acidity and basicity, and predict species at equilibrium when compounds are mixed. 4. Identify which pairs of structures represent resonance structures. 5. Indicate which structure is the more stable resonance contributor for identified resonance structure pairs.

Uploaded by

Nicholas Ow
Copyright
© Attribution Non-Commercial (BY-NC)
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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School of Physical & Mathematica l Sciences

Division of Chemistry & Biological Chemistry

H3 Organic Synthesis and Mechanism - Tutorial 1

Structure, Bonding, Resonance and Acid-Base Theories

1) For the following compounds, determine the formal charges for the atoms
marked with an asterisk (*):
O* H
H H H O*
O* H2C* N* N*
C*
H H H O*

2) Identify the most acidic H in the following compounds:


O
O H
N
OH OH
H

O O O O O
OH
O

3) Use the pKa table supplied to answer the following questions.

a) List the following in order of increasing acidity:


A B C D E

O N N
H H HO CH3 H CH3
O

b) List the following in order of increasing basicity:


O O
S OH
OH
O
F G H I J

c) By comparing pKa values, predict the predominant species at


equilibrium when you mix....
i) compound H with compound D
ii) compound A with compound F
iii) compound G with compound C
School of Physical & Mathematica l Sciences
Division of Chemistry & Biological Chemistry

4) Which of the following pairs represent resonance structures?


O O
and
OH O and

O O
O OH
and
and

O O

O O
and
H 2C N and H2C N
O O

H H
H3C N N and H3C N N O O
and

H H H H

5) For the pairs of resonance structures above, indicate which is the more
stable resonance contributor.
School of Physical & Mathematica l Sciences
Division of Chemistry & Biological Chemistry

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