SI Exam 1 Review Handout
Chapter 1
Formal Charge:
Give the formal charge of each charged atom in the molecule below:
Hybridization:
For each of the indicated atoms below, give the hybridization state of the atom, its
molecular geometry, and its approximate bond angles.
1
Constitutional Isomers:
For each pair of molecules below, state whether the molecules are constitutional isomers,
the same molecule, or neither.
A. Constitutional Isomers
B. Same Molecule
C. Unrelated Molecules (Not Isomers)
A. Constitutional Isomers
B. Same Molecule
C. Unrelated Molecules (Not Isomers)
A. Constitutional Isomers
B. Same Molecule
C. Unrelated Molecules (Not Isomers)
2
Resonance:
Draw all possible resonance structures for the following molecules and select the major
contributor.
3
Chapter 2
Functional Groups:
Circle and identify each of the functional groups present in the following molecules.
Codeine
Heroin
Melting/Boiling Point:
Which of the following molecules would have the highest boiling point?
A)
B)
C)
D)
HOCH2CH2OH
CH3COCH3
CH3CH2CH2OH
CH3CH2CH2F
Rank the following molecules in order of boiling point. Do the same for melting point.
4
Solubility:
Which of the following molecules is most likely to dissolve in hexane?
A)
B)
C)
D)
E)
Ethanol
CCl2H2
CH3OCH3
(CH3)2CHCH2CH3
NH3
Which of the following molecules is most likely to dissolve in water?
A)
B)
C)
D)
E)
BH3
CCl4
CH3COOH
CO2
CH3CH2CH3
5
Infrared Spectroscopy:
Which IR spectrum correlates to each of the following compounds?
Compound:______
Compound:______
Compound:______
Compound:______
6
Which of the following molecules will give a C-H stretching signal below 3000 cm-1? (Hint:
There may be multiple answers)
Which of the following molecules will give a sharp peak between 2100 and 2300 cm-1 and a
sharp peak at 3300 cm-1? (Hint: There may be multiple answers)
Which of the following molecules will give a sharp peak between 2100 and 2300 cm-1 but no
sharp peak at 3300 cm-1? (Hint: There may be multiple answers)
7
Which of the following molecules most likely gave the IR spectrum given below?
IR Spectrum:
Chapter 3
Acid-Base Strength:
Choose the stronger acid in each pair.
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Choose the stronger base in each pair.
Gibb’s Free Energy and Leveling Effect:
For each reaction below, determine if the ∆G° for the reaction in the forward direction will
be negative or positive. How about the Keq? Would the reaction be spontaneous?
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