Organic Chemistry Quiz

Test Your General Knowledge of Organic Chemistry

Question 1:What is the most stable conformation of cyclohexane?
boat
twist-boat
planar-hexagonal
diradical
chair
Question 2:When HCl adds to R2C=CHR, Markovnikov's rule predicts which of the following?
H adds to the carbon with the most hydrogens
H adds to the carbon with the most alkyl groups
Cl adds to the carbon with the most hydrogens
no reaction takes place
an explosion will occur
Question 3:Olefins may be oxidatively cleaved to carbonyl containing products using which of the following reagents?
HBr/peroxides
ozone ozone followed by zinc/acid
chlorine in carbon tetrachloride
hydrogen and palladium
potassium hydroxide in a 2:1 chloroform:water mixture
Question 4:Alkynes may be reduced to trans olefins using which of the following reagents?
hydrogen, lindlar catalyst
hydrogen, palladium catalyst
lithium, ammonia
HCl in ether
disiamylborane and hydrogen peroxide
Question 5:Which of these compounds is chiral?
3-ethyl-5,5-dimethylheptane
cis-1,4-dichlorocyclohexane
2,4-dimethylheptane
butane
cyclohexane
Question 6:To prepare a tertiary alkyl chloride from its alcohol,
react the alcohol with SOCl2/pyridine
react the alcohol with a Grignard reagent (RMgCl)
react the alcohol with NBS in carbon tetrachloride
react the alcohol with HCl/ether
react the alcohol with natural gas
Question 7:The SN1 reaction works best with
primary alkyl halides and tosylates
aryl halides and triflates
primary alcohols
tertiary, allylic, and benzylic halides and tosylates
secondary olefins and alkynes
Question 8:Carbonyl functional groups absorb IR light with sharp, intense peaks in which region of the IR spectrum?
1320-1520 cm-1
2000-2500 cm-1
1670-1780 cm-1
1000-1110 cm-1
100-270 cm-1
Question 9:How many types of nonequivalent protons are there in p-xylene?
1
3
4
2
5
Question 10:When 1,3-butadiene reacts with HCl, the 1,2 adduct is said to be which product?
thermodynamic
Diels-Alder
kinetic
Simmons-Smith
antibonding
Question 11:Predict the major product of mononitration of methoxybenzene.
o-methoxynitrobenzene only
p-methoxynitrobenzene only
m-methoxynitrobenzene only
o-methoxynitrobenzene and p-methoxynitrobenzene
o-methoxynitrobenzene and m-methoxynitrobenzene
Question 12:A primary alcohol can be oxidized to an aldehyde using which of the following reagents.
Jones reagent
POCl3/pyridine
LiAlH4, ether
PCC/CH2Cl2
hydrochloric acid in water, followed by dilute NaOH
Question 13:In the Wittig reaction,
a ketone may be obtained from an olefin
an aldehyde is oxidized to a carboxylic acid
an olefin may obtained from a ketone
an imine is formed from a ketone
a thiol reacts with a ketone to yield a thioacetal
Question 14:Which is more acidic: benzoic acid, p-methylbenzoic acid, or p-chlorobenzoic acid?
p-chlorobenzoic acid
p-methylbenzoic acid
benzoic acid
all are equally acidic
Question 15:Which of the following is the most reactive towards NaOH? least reactive?: acid anhydride, acid chloride, carboxylic acid, ester, amide
most reactive = amide, least reactive = acid chloride
most reactive = acid chloride, least reactive = carboxylic acid
most reactive = ester, least reactive = acid anhydride
most reactive = acid chloride, least reactive = ester
most reactive = ester, least reactive = carboxylic acid
Question 16:Nitriles may be alkylated using which of the following sequences of reagents.
1. sodium ethoxide in ethanol 2.alkyl halide
1. sodium hydroxide in water 2. alkyl halide
1. bromine and PBr3 2. Grignard reagent
1. LDA in THF 2. alkyl halide
1. peroxides 2. LDA
Question 17:The Michael addition reaction involves
an intermolecular aldol condensation
an intramolecular aldol condensation
a 1,4 conjugate addition
a mixed Claisen reaction
a cyclization followed by an elimination
Question 18:Arenediazonium salts are formed by reaction of
an aromatic amine with hydrogen and palladium
an aromatic amine sodium dichromate
an aromatic amine with nitrous acid
an aromatic amine with potassium nitrosodisulfonate
benzoquinone with fremy's salt
Question 19:For any single reaction step, the geometry of the transition state for that step resembles the side to which it is closer in free energy. This is known as
The Principle of Microscopic Reversibility
Marcus Theory
The Baldwin Rule
The Hammond Postulate
The Third Law of Thermodynamics
Question 20:Which of the following is NOT aromatic?
benzene
naphthalene
cyclooctatetraene
cyclopentadienyl anion
cycloheptatrienyl cation
Question 21:A carbon atom in ethylene is of what hybridization?
sp
sp3
sp3d
sp3d2
sp2
Question 22:The addition of water to an olefin by hydroboration-oxidation results in
Markovnikiov syn addition of water to the double bond
non-Markovnikov syn addition of water to the double bond
non-Markovnikov anti addition of water to the double bond
Markovnikov anti addition of water to the double bond
no reaction
Question 23:How many absorptions would you see in the 13C NMR spectrum of tert-butylcyclohexane?
10
8
6
5
6
Question 24:Which of the following is a ortho- and para- directing deactivator in Electrophilic Aromatic Substitution?
CHO
Cl
OH
NHCOCH3
NH2
Question 25:The product of the reaction of acetone with 2 equiv of methanol in the presence of acid is
no reaction
acetic acid
2,2-dimethoxypropane
methyl acetate
acetic anhydride
Question 26:In the acid-catalyzed ring opening of an unsymmetrical epoxide, the nucleophile attacks primarily at the more highly substituted carbon. The reason for this is:
steric hindrance at the more substituted carbon atom
steric hindrance at the less substituted carbon atom
the more substituted carbon atom stabilizes the carbocation
the less substituted carbon atom stabilizes the carbocation
the more substituted carbon atom stabilizes the anion
Question 27:Grignard reagents react with ketones to give:
secondary alcohols
primary alcohols
tertiary alcohols
esters
carboxylic acids
Question 28:Which is the most basic: ammonia, methylamine, ethylamine, trimethylamine, triethylamine
trimethylamine
ethylamine
triethylamine
methylamine
ammonia
Question 29:The Williamson ether synthesis is an example of an:
SN2 reaction
SN1 reaction
E2 reaction
E1 reaction
SAR3 reaction
Question 30:The approximate proton chemical shift of a vinylic proton is:
1.3-1.8 ppm
4.6-5.7 ppm
7-8 ppm
11-12 ppm
20-23 ppm

This Quiz has been designed by David Flosser.