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Unit Test #1, Chem. 331, Summer 2002

Answer Key

1. Which molecules contain both covalent and ionic bonds?

CH 3 OH Answer

Na

NH 4 Cl

2.

Na 2 CO 3

NH 4 Cl (Corrected from NH 3 Cl)

2 CO 3

Carbon has how many valence electrons?

NaCl

 

Answer

4

3.

Using the VSEPR model, circle the molecules in which the

indicated atom has bond angles of about 120°.

in which the indicated atom has bond angles of about 120°. Answer I and III 4.

Answer

I and III

4. Which molecules are polar?

H

H H O CCH C CH 2 Cl 2 C C H H H H
H
H
O
CCH
C CH 2 Cl 2
C
C
H
H
H
H
I
II
III
IV

Answer II, III, and V

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CH 3 OH

V

Unit Test #1, Chem. 331, Summer 2002

Answer Key

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

following compounds?

a) NaNH 2

b) N 2

c) NH 4 Cl

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 O H 3 C + HCL O + Cl H 3 C H H
H
O
H 3 C
+ HCL
O
+
Cl
H 3 C
H
H
I
II
III
IV
O
H 3 C
H 3 C
O
Na
+ NaH
+ H 2
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. H 2 O

IV. NH 3

Need to look at conjugate acid (pKa)

H 2 O (15.7)

HCl (-7)

H 3 O + (-1.74)

NH 4 + (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
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?

d) 11. Which pairs of molecules are constitutional isomers? Answer d). different compound a) and b)

Answer d).

different compound

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

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Unit Test #1, Chem. 331, Summer 2002

Answer Key

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

12. Which conformation of 2-methylbutane is the most stable? Answer b) which has one gache interaction.

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?

below represent cis forms of 1,2- dimethylcyclohexane? Answer I and IV 14. What is the classification

Answer I and IV

14. What is the classification of the indicated carbon?

Answer I and IV 14. What is the classification of the indicated carbon? a) 1° b)

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?

Key 15. Which is the IUPAC name for the compound below? Answer trans -1-ethyl-2-methylcyclohexane 16. Which

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 H 4 Cl
3
R
Priorities
2
H
4
Cl

lowest priority is pointing

back (how nice of me)

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 Chiral Chiral
1
2
Cl
Cl
Cl
Cl
Chiral
Chiral
mirror plane 3 so achiral Cl Cl Cl Cl same compound MESO
mirror plane
3
so achiral
Cl
Cl
Cl
Cl
same compound
MESO

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enantiomer pairs

1,2

diasteriomer pairs

1,3

2,3

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?

H

O C H 3 C CH 2 CH 2 H H
O
C
H 3 C
CH 2
CH 2
H
H
acetaldehyde pKa = 22 ethane pKa = 51 conjugate bases O C H 3 C
acetaldehyde
pKa = 22
ethane
pKa = 51
conjugate bases
O
C
H 3 C
H
CH 2
CH 2

no inductive effect or resonance structures

H

O C CH 2 O O C C H H CH 2
O
C
CH 2
O
O
C
C
H
H CH 2
or resonance structures H O C CH 2 O O C C H H CH 2

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

towards it, reducing the full negative charge on the carbon CH 2 major contributor Resonance A
towards it, reducing the full negative charge on the carbon CH 2 major contributor Resonance A

CH 2

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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