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Unit Test #1, Chem.

331, Summer 2002 Answer Key

1. Which molecules contain both covalent and ionic bonds?

CH3OH Na2CO3 NH4Cl (Corrected from NH3Cl) NaCl


Answer
Na2CO3
NH4Cl

2. Carbon has how many valence electrons?


Answer
4

3. Using the VSEPR model, circle the molecules in which the


indicated atom has bond angles of about 120°.

Answer
I and III

4. Which molecules are polar?

O H H

H C C H CH2Cl2 C C CH3OH
C
H H H H
I II III IV V
Answer
II, III, and V

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Unit Test #1, Chem. 331, Summer 2002 Answer Key

5. Nitrogen has a negative formal charge in which of the


following compounds?

a) NaNH2
b) N2
c) NH4Cl
d) HCN
Answer a)
6. List the bonds in order of increasing acidity (least to most).
C-H O-H F-H N-H
I II III IV

I<IV<II<III
Follows electronegativity of atom attached to hydrogen.
7. Circle the Bronsted-Lowry acids in the following reactions.
H
H3C O
+ HCL H3C O + Cl
H
H
I II III IV

H3C O
+ NaH H3C O Na + H2
H

V VI VII VIII
Answer
II, III, V, and VIII
Remember there is always a conjugate acid to every base
8. Arrange the following in order of increasing basicity (weakest
to strongest).
I. OH- II. Cl- III. H2O IV. NH3
Need to look at conjugate acid (pKa) +
H2O (15.7) HCl (-7) H3O (-1.74) NH4+ (9.24)
Strongest acid to weakest acid gives weakest base to strongest
base
II<III<IV<I

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Unit Test #1, Chem. 331, Summer 2002 Answer Key

9. Which is the stronger base if the equilibrium lies considerably to the right?

O O
+ HCN
C + CN C
H OH H O

I II III IV
Answer
II, if equilibrium lies towards the weakest acid its conjugate
base will be stronger
10. Which of the following properties are not identical for
constitutional isomers?
I. molecular formula
II. molecular weight
III. order of attachment of atoms
IV. physical properties
a) I, IV
b) II, III
c) I, II
d) III, IV
Answer d)
11. Which pairs of molecules are constitutional isomers?

Answer d). a) and b) are identical and c) is not an isomer but a


different compound

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Unit Test #1, Chem. 331, Summer 2002 Answer Key

12. Which conformation of 2-methylbutane is the most stable?

Answer b) which has one gache interaction. a) is eclipsed,


always a problem, and c) and d) both have two gauche interactions
13. Which structural formulas below represent cis forms of 1,2-
dimethylcyclohexane?

Answer I and IV
14. What is the classification of the indicated carbon?

a) 1°
b) 2°
c) 3°
d) 4°
Answer c)

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Unit Test #1, Chem. 331, Summer 2002 Answer Key

15. Which is the IUPAC name for the compound below?

Answer
trans-1-ethyl-2-methylcyclohexane

16. Which compounds contain stereocenters?


I. 1-chloropentane
II. 2-chloropentane
III. 3-chloropentane
IV. 1,2-dichloropentane
Answer II, IV
17. Give the proper IUPAC name for the following compound,
including R or S configuration,

3
R
Priorities
2

lowest priority is pointing


H 4 back (how nice of me)
Cl
1
Answer R-2-chlorobutane

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Unit Test #1, Chem. 331, Summer 2002 Answer Key

18. For the compound 1,2-dichlorocyclopentane draw all the


possible sterioisomers and assign them numbers 1, 2, 3, etc.
Which isomers are chiral? Achiral? Meso? Give all the pairs of
enantiomers and all the pairs of diasteriomers.

1 2
Cl Cl

Cl Cl
enantiomer pairs
Chiral Chiral 1,2

diasteriomer pairs
1,3
2,3
mirror plane 3
so achiral Cl Cl

Cl Cl

same compound
MESO

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Unit Test #1, Chem. 331, Summer 2002 Answer Key

19. Account for the increased acidity of acetaldehyde over that


of ethane in terms of inductive and resonance effects (by looking
at the conjugate base). For all resonance contributors use the
curvy arrows to show how to go from one contributor to the other.
Which is the major contributor?

C H3C
H CH2 CH2

H H

acetaldehyde ethane
pKa = 22 pKa = 51
conjugate bases
O

C H3C
H CH2 CH2 no inductive effect or
resonance structures

C
H CH2

inductive effect
electronegativity of oxygen pulls electron density towards it, reducing the full
negative charge on the carbon

O O

C C
H CH2 H CH2
major contributor

Resonance
A second resonance structure can be drawn for the acetaldehyde conjugate base.
Again spreading the negative charge throughout the molecule. The second
resonance structure is the major contributor as the negative charge is on the
oxygen.

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