Houston spring final exam
CHEM 2325: ORGANIC CHEMISTRY II
University of Houston – Questions with Answers & Rationales
Based on L.G. Wade & J.M. Simek, Organic Chemistry (9th Edition)
Exam Structure Note: The course has 3 evening exams (lowest dropped) and a
cumulative final. 40% of the final is the American Chemical Society (ACS)
standardized exam covering both CHEM 2323 & 2325, while 60% is the UH exam .
TOPIC 1: AROMATIC COMPOUNDS & ELECTROPHILIC AROMATIC SUBSTITUTION
(EAS) (Q1-Q25)
Q1. According to Hückel's rule, which compound below is considered aromatic?
A) Cyclobutadiene
B) Cyclooctatetraene
C) Benzene
D) 1,3-Cyclohexadiene
,Answer: C
Rationale: Hückel's rule states that a planar, cyclic, conjugated molecule must
have
4
n
+
2
4n+2 π electrons to be aromatic. Benzene has 6 π electrons (
n
=
1
n=1). Cyclobutadiene has 4 (
n
=
1
n=1, anti-aromatic). Cyclooctatetraene is non-planar, so it is non-aromatic.
Q2. When chlorobenzene undergoes nitration (
H
,N
O
3
/
H
2
S
O
4
HNO
3
/H
2
SO
4
), the major product is:
, A) ortho-nitrochlorobenzene
B) meta-nitrochlorobenzene
C) para-nitrochlorobenzene
D) A mixture of ortho and para
Answer: D
Rationale: The Chlorine atom is an ortho/para director and a ring deactivator. It
directs the incoming electrophile to the ortho and para positions. While chlorine
withdraws electrons inductively, it donates electrons by resonance, stabilizing the
intermediate at the ortho/para positions.
Q3. Which of the following substituents is a meta-director on a benzene ring?
A) -OH
B) -OCH₃
C) -NO₂
D) -CH₃
Answer: C
Rationale: The nitro group (
−