CH202 Midterm 1 Information and Practice - 2024

Midterm 1 Format Content:

Midterm 1 will take place in class on Thursday, February 8th.

The test will consist of approximately 10 multiple choice questions (approx. 10 marks), as well as short
answer questions (approx. 30 marks).

The content will include material from Chapters 1-5. Approximate mark breakdown (keep in mind some
of the foundational concepts from chapters 1 and 2 are needed to understand subsequent chapters):

Chapter 1: 2 marks

Chapter 2: 5 marks

Chapter 3: 12 marks

Chapter 4: 10 marks

Chapter 5: 11 marks

The attached practice questions are meant to give you a sense of the type and format of questions being
asked. It may not be completely comprehensive but does cover most of the concepts and material
covered on the midterm.

Additional Suggested practice:

WileyPLUS homework from chapters 1-5.

Some suggested textbook questions:

Chapter 1: Skill Builder questions: 1.1, 1.3, 1.4, 1.7, 1.10, 1.11, 1.13, 1.21, 1.24, 1.25, 1.28, 1.30

Chapter 2: Skill builder questions: 2.4, 2.8, 2.12, 2.13, 2.15, 2.25, 2.26; Practice Problems: 2.40, 2.41

Chapter 3: Skill builder questions: 3.1, 3.2, 3.3, 3.4, 3.6, 3.7, 3.10, 3.13, 3.15, 3.18, 3.19, 3.20, 3.23, 3.24,
3.35; Practice problems: 3.37, 3.47, 3.49, 3.51, 3.54

Chapter 4: Skill builder questions: 4.4, 4.8, 4.9, 4.14, 4.16, 4.17, 4.18, 4.19, 4.21, 4.25, 4.27, 4.28, 4.30,
4.32; Practice problems: 4.43, 4.53, 4.56

Chapter 5: Skill builder questions: 5.4, 5.7, 5.9, 5.11, 5.12, 5.15, 5.16, 5.19, 5.23, 5.26; Practice problems:
5.31, 5.33, 5.37, 5.39, 5.44, 5.45
Sample Multiple Choice Questions:

1. Which compound has the shortest carbon-carbon bond(s)?

(a) H3CCH3 (b) H2C=CH2 (c) HC≡CH (d) CH3CH2CH3

(e) All carbon-carbon bonds are the same length.

2. What is the relationship between the following structures?

O (a) resonance forms

NH 2 NH 2 (b) strained at best
HO HO
O
(c) stereoisomers

(d) constitutional isomers

3. Which of the structures below contain an oxygen with a formal charge of +1?

H
O O
(a) (i) and (ii)
C O O C
H O H H H CH3 H H (b) (iii) and (iv)
H
(i) (ii) (iii) (iv) (c) (ii) and (iii)

(d) (i) and (iv)

4. How many sigma () bonds and pi () bonds does the following structure possess?

H H (a) 10 sigma () bonds and 2 pi () bonds

H C C H
C C C (b) 10 sigma () bonds and 4 pi () bonds
H H H H (c) 12 sigma () bonds and 2 pi () bonds

(d) 14 sigma () bonds and 0 pi () bonds

5. Which of the following carbon-carbon bonds is the shortest?

6. Which of the following species is NOT trigonal pyramidal?

7. What is the hybridization state of the indicated carbon?

H CH 3 (a) sp2
C C
H CH 3 (b) sp

(c) s2p

(d) sp3

8. Which of the following compounds has the lowest boiling point?

9. In the Lewis structure below, nonbonding electron pairs have been intentionally omitted. How many
nonbonding electron pairs should be present in the structure?

(a) 5 (b) 4 (c) 7 (d) 6

10. Which of the following Lewis structures has delocalized electrons?

(a) (i) and (ii) (b) (i) and (iii) (c) (iii) and (iv) (d) (ii) and (iv)
11. Which set of curved arrows are required to convert the resonance form on the left to the resonance
form on the right?

12. For each of the following pairs of resonance contributors, indicate the one that would
contribute more to the resonance hybrid, i.e., the one that is more stable.

(a) I and IV (b) I and III (c) II and IV (d) II and III

13. Below is a Brönsted-Lowry acid/base reaction. Which of the following statements is TRUE?

NaH + H 3C C C H H2 + H3C C C Na
I II III IV

(a) I is the base, II is the acid; III is the conjugate base, IV is the conjugate acid.

(b) I is the base, II is the acid; III is the conjugate acid, IV is the conjugate base.

(c) I is the acid, II is the base; III is the conjugate base, IV is the conjugate acid.

(d) I is the acid, II is the base; III is the conjugate acid, IV is the conjugate base.
14. Rank the following from least acidic to most acidic.

Cl I F Br
OH OH OH OH
I II III IV

(a) III (least acidic) < I < IV < II (most acidic)

(b) II (least acidic) < I < IV < III (most acidic)

(c) II (least acidic) < IV < I < III (most acidic)

(d) III (least acidic) < IV < I < II (most acidic)

15. Three of the structures below represent constitutional isomers. Which one does NOT?

16. Which of the following represents the most stable conformation of 1-bromopropane?

17. Which of the following statements about cyclopropane is true?

(a) It has no angle strain and no torsional strain.

(b) It has both angle strain and torsional strain.
(c) It has angle strain but no torsional strain.
(d) It has torsional strain but no angle strain.
18. Which of the following structures represents cis-1,3-dichlorocyclohexane?

19. The following compound possesses two chirality centres labeled ‘a’ and ‘b’. What is the stereochemical
configuration (R vs S) of these chirality centres?

Br H (a) a: R; b: R
a Cl
b (b) a: R; b: S
Cl
H Cl
(c) a: S; b: R

(d) a: S; b: S

20. If a solution of a compound (30.0 g/100 mL of solution) has a measured rotation of +15° in a 2 dm
tube, what is its specific rotation?

(a) +25° (b) +90° (c) +2.5° (d) +9°

21. What is the relationship between the following compounds?

CH3 CH2CH 3
Br H Br H
Br H H3C H
CH2CH 3 Br

(a) identical (includes different conformations of the same compound)

(b) enantiomers

(c) diastereomers

(d) constitutional isomers

 Practice Short Answer Questions:

1. (a) Draw a Lewis structure for acetonitrile, H3CCN. Explicitly show (but no need to label) all sigma- and
pi-bonds and include nonbonding electron pairs and formal charges as needed.

(b) Consider the following Brönsted-Lowry acid-base reaction:

CH3CN + Na+ H2N Na+ CH2CN + NH3

A B C D

In the space below, provide a curved arrow mechanism to show how the reaction proceeds from left to
right. Note that Na+ is a spectator ion and is not involved in the reaction mechanism.

(c) The anion depicted in ‘C’ above (i.e., −:CH2CN) has two significant resonance forms. Draw both
resonance forms and circle the one that contributes most to the resonance hybrid, i.e., the one that is
most stable. Note that Na+ is a spectator ion and should NOT be included in the structures below. (2)
2. For each of the following reactions:

(a) Label the acid, the base, the conjugate acid, and the conjugate base. (Note that the counterions have
been omitted).

(b) Draw curved arrows to show the flow of electrons for reach reaction.

(c) Using the pKa values in table 3.1 of the text, predict whether the reaction will proceed in the forward
direction.

3. For the following pairs of compounds, circle the one that is more acidic and provide an explanation (in
no more than 2 sentences).
4. For the following Lewis Acid-base reaction, identify the Lewis acid and Lewis base, and supply curved
arrows to depict the reaction shown. Also, add formal charges to the appropriate atoms in the product.

5. Draw Newman projection representations for the most stable and the least stable conformations of
3,3-dimethylpentane when viewed down the C2-C3 bond with C2 in front and C3 in back. Clearly indicate
which representation is most stable and which is least stable.

6. Flovent is an anti-inflammatory that is sometimes used in inhalers for the treatment of asthma. How
many chirality centres does Flovent possess? Circle each one. (For more practice, see practice problems
5.33, 5.37)

O
O
O
HO S F

F
O Flovent
F
7. Assign R or S configuration to the chirality centres in each of the following compounds. (For more
practice, see practice problems 5.31, 5.39)

8. For each of the following pairs of compounds, determine the relationship between them (i.e.
enantiomers, diastereomers, constitutional isomers, or identical (including different conformations of the
same compound)). For more practice, see practice problems 5.44, 5.45)

9. For each of the following compounds, how many stereoisomers exist? Draw all of the stereoisomers as
Fischer projections with the carbon chain along the vertical axis