CHEM 219
Principles of Organic Chemistry
MODULE 1 - 8 PROBLEM SET
Portage Learning
Inside you will get:
- Structural drawing and identification exercises
- Nomenclature practice questions
- Mechanism-writing and prediction of reaction products
- Stereochemistry assignments involving chiral centers and
configuration descriptors
- Application-based problems requiring interpretation of reaction conditions and
outcomes
,Table of Contents
Module 1 Problem Set:.............................................................................. 2
Module 2 Problem Set: ............................................................................ 11
Module 3 Problem Set: ............................................................................ 18
Module 4 Problem Set: ............................................................................ 28
Module 5 Problem Set............................................................................. 36
Module 6 Problem Set............................................................................. 44
Module 7 Problem Set............................................................................. 48
Module 8 Problem Set............................................................................. 51
Module 1 Problem Set:
ANSWERS IN RED
1. To help yourself, write out the Lewis Dot Diagram for each of the indicated
elements on a piece of scratch paper; determine the following for each and
fill in the chart with your answers:
A. The number of Lone Pairs the atom possesses in its valence shell.
B. The number of Unpaired Electrons the atom possesses in its valence shell.
C. The number of bonds the atom will form.
ANSWER:
1. Oxygen: A) 2 B) 2 C)2
2. Carbon: A) 0 B) 4 C) 4
3. Hydrogen: A) 0 B)1 C) 1
4. Nitrogen: A) 1 B) 3 C) 3
,2. Classify the bonding between the given pairs of atoms as ionic, covalent, or
polar covalent. Use the table of electronegativities shown below to help with
the classification.
a. Br and Br = covalent
b. K and Cl = Ionic
c. P and Cl = Polar Covalent
d. C and O = Polar Covalent
e. Na and Br = Polar Covalent
, 3. Define the term constitutional isomer.
CHANGE WORDING Answer:
Two (or more) different chemical compounds with the same molecular formula but
different connectivity between the atoms in their structural formulae.
4. Explain (using specific evidence) what makes the following two
compounds constitutional isomers of one another:
Both compounds have a MF of C3H6O – same MF.
Compound “a” has a 3-carbon chain with a C=O in the middle. No H atom
connected to C of C=O.
Compound “b” has a 3-carbon chain with a C=O at the end. There is an H
attached to the C of the C=O.
5. What is the relationship between the compounds shown? Are they the same
compound, constitutional isomers, or two different compounds that are not related to
one another? Explain.
Different compounds that are not related. They have different MF – (a) C3H8O, (b)
C3H6O.
6. Identify each of the following carbon skeletons as linear (continuous),
branched, or cyclic.
Principles of Organic Chemistry
MODULE 1 - 8 PROBLEM SET
Portage Learning
Inside you will get:
- Structural drawing and identification exercises
- Nomenclature practice questions
- Mechanism-writing and prediction of reaction products
- Stereochemistry assignments involving chiral centers and
configuration descriptors
- Application-based problems requiring interpretation of reaction conditions and
outcomes
,Table of Contents
Module 1 Problem Set:.............................................................................. 2
Module 2 Problem Set: ............................................................................ 11
Module 3 Problem Set: ............................................................................ 18
Module 4 Problem Set: ............................................................................ 28
Module 5 Problem Set............................................................................. 36
Module 6 Problem Set............................................................................. 44
Module 7 Problem Set............................................................................. 48
Module 8 Problem Set............................................................................. 51
Module 1 Problem Set:
ANSWERS IN RED
1. To help yourself, write out the Lewis Dot Diagram for each of the indicated
elements on a piece of scratch paper; determine the following for each and
fill in the chart with your answers:
A. The number of Lone Pairs the atom possesses in its valence shell.
B. The number of Unpaired Electrons the atom possesses in its valence shell.
C. The number of bonds the atom will form.
ANSWER:
1. Oxygen: A) 2 B) 2 C)2
2. Carbon: A) 0 B) 4 C) 4
3. Hydrogen: A) 0 B)1 C) 1
4. Nitrogen: A) 1 B) 3 C) 3
,2. Classify the bonding between the given pairs of atoms as ionic, covalent, or
polar covalent. Use the table of electronegativities shown below to help with
the classification.
a. Br and Br = covalent
b. K and Cl = Ionic
c. P and Cl = Polar Covalent
d. C and O = Polar Covalent
e. Na and Br = Polar Covalent
, 3. Define the term constitutional isomer.
CHANGE WORDING Answer:
Two (or more) different chemical compounds with the same molecular formula but
different connectivity between the atoms in their structural formulae.
4. Explain (using specific evidence) what makes the following two
compounds constitutional isomers of one another:
Both compounds have a MF of C3H6O – same MF.
Compound “a” has a 3-carbon chain with a C=O in the middle. No H atom
connected to C of C=O.
Compound “b” has a 3-carbon chain with a C=O at the end. There is an H
attached to the C of the C=O.
5. What is the relationship between the compounds shown? Are they the same
compound, constitutional isomers, or two different compounds that are not related to
one another? Explain.
Different compounds that are not related. They have different MF – (a) C3H8O, (b)
C3H6O.
6. Identify each of the following carbon skeletons as linear (continuous),
branched, or cyclic.
