Download as pdf or txt
Download as pdf or txt
You are on page 1of 4

University of the Philippines Association of

Chemistry Majors and Enthusiasts (UP ACME)


CHEM 33 1st LONG EXAM SAMPLEX
1st Semester, A.Y. 2022-2023

I. Modified True or False. Write TRUE if the statement is correct. If the statement is false,
CHANGE the underlined word to make the statement correct.
1. A π-bond is stronger than a σ-bond.
2. The hybridization of both carbon atoms in acetylene is sp.
3. In a reaction, the rate-determining step has the highest activation energy.
4. Iso-pentane and n-pentane are stereoisomers.
5. The boat conformation of cyclohexane is the most stable conformation of the
compound.
6. The formation of an internal alkene is thermodynamically favored than that of the
terminal alkene.
7. In ozonolysis with oxidative workup, aldehyde by-products are oxidized into alkyl
halides.
8. Butyne has higher boiling point than ethyne.
9. In the addition of a hydroxide, the hydrohalogenation of alkynes will follow anti-
Markovnikov rule.
10. In IR spectroscopy, higher energy stretching bands occur at lower wave numbers on the
cm-1 scale.

II. Multiple Choice. Choose the letter of the best answer.


1. A certain organic compound has a molecular formula of C5H8. Given this information,
the compound cannot be a/an _______.
a. diene c. alkyne
b. cycloalkene d. linear straight chain alkane

2. Which of the following structures will yield methylcyclopentane when subjected to


catalytic hydrogenation?

a. b. c. d. All of the above

3. Which of the following is true about cis-1,2-dimethylcyclopropane and trans-1,2-


dimethylcyclopropane?
a. cis-1,2-dimethylcyclopropane is more stable.
b. trans-1,2-dimethylcyclopropane is more stable.
c. Both are equally stable.
d. Stability of both compounds cannot be determined.

4. Which kind of organic reactions can reactions A and B be classified, respectively?

CHEM 17 | 2nd Sem, AY 2021-2022 UP ACME


a. substitution, addition c. elimination, substitution
b. elimination, addition d. substitution, elimination

5. Consider isopropylcyclobutane and 1,1-dimethylcyclopentane.

Which of the following statements is true when both compounds undergo


monohalogenation with Br2 and UV?
a. Isopropylcyclobutane has more unique products than 1,1-dimethylcyclopentane.
b. 1,1-dimethylcyclopentane has more unique products than isopropylcyclobutane
c. Isopropylcyclobutane and 1,1-dimethylcyclopentane both have the same number of
unique products
d. cannot be determined

6. Rank the following from lowest to highest boiling point: heptane, decane, undecane,
nonane
a. nonane < heptane < undecane < decane
b. undecane < nonane < heptane < decane
c. undecane < decane < nonane < heptane
d. heptane < nonane < decane < undecane

7. Which of the following has the highest heat of hydrogenation?

c.
a.

b. d.

For Items 8 – 11, refer to 2-methylpent-2-ene, as shown.


8. Which of the following is formed with the addition of H2?

a. c.

b.
d.

9. Which of the following is the product upon addition of HCl and peroxide?

c.
a.

b. d.

10. Which of the following is formed upon addition of O3 and DMS?

a. c.

b.
d.

11. At 160oC, hydroboration of 2-methylpent-2-ene is reversible. Which of the following is


not a possible product when the compound undergoes hydroboration-oxidation at this
temperature?
c.
a.

b. d.

12. Which of the following can undergo keto-enol tautomerism?

a. A and C only c. A and M only


b. A, M, and E only d. A, C, and E only

13. Which reagent is needed to complete the reaction below?

a. Na/NH3 c. H2, Lindlar’s catalyst


b. 2H2, Pt d. H2, LiNH2

14. Identify the reagent needed to complete the reaction below.

a. O3, H2O c. O3, Zn, H3O+


b. H2O, HgSO4, H2SO4 d. BH3, NaOH, H2O2

15. Which unsaturated bond will be detected in the IR region?

a.
c.

b.

d.

You might also like