Organic Chemistry Practice Problems
Organic Chemistry I Practice Set #3 (Chapters 1-2 - Carey)
1) For the compound given to the right, provide a name.
2) For each of the following, consider the compound given in problem 1.
(a) How many tertiary H’s are there?
(b) How many methylene groups are there?
(c) How many quarternary Cs are there?
(d) How many primary Cs are there?
3) Provide a structure for 4-(tert-butyl)-1-isobutyl-2-isopropyl-1-methyl-6-(2-methylbutyl)cyclopheptane.
Provide a complete structural formula – showing all atoms and all bonding valence electrons.
4) Consider molecule A shown to the right. Remember your Lewis structure
rules.
a. Using Lewis structures for reactants and products and using curved
arrows to show the flow of electrons in molecule A, give the chemical
equation that shows the heterolytic dissociation of one of the six
primary CH bonds in molecule A to give H+ and the corresponding
conjugate base. If resonance structures exist for the conjugate base, give all important resonance
structures for the conjugate base. Clearly indicate the value of each of the three CCC bond angles
in this conjugate base of molecule A.
b. Using Lewis structures for reactants and products and using curved arrows to show the flow of
electrons in molecule A, give the chemical equation that shows the heterolytic dissociation of
one of the two secondary CH bonds in molecule A to give H+ and the corresponding conjugate
base. If resonance structures exist for the conjugate base, give all important resonance structures
for the conjugate base. Clearly indicate the value of each of the three CCC bond angles in this
conjugate base of molecule A.
c. Using structural considerations, identify which of the two Hs is the more acidic one. Provide a
clear, concise explanation.
5) Draw structural formulas for 5 (and only 5) constitutional isomers that have one three-membered ring
and the molecular formula C5H10O. Your structural formulas must have no nonzero formal charges and
the most typical arrangements of bonding and nonbonding valence elections. Provide complete
structural formulas – showing all atoms and all bonding valence electrons.
6) Using the molecular formula for the compound shown to the right in the chemical equation, give the
balanced chemical equation for the combustion of the compound shown.
This resource was prepared by the Tallahassee Community College Learning Commons
Adapted from practice handouts created by Dr. EF Hilinski of Florida State University
