Characteristic sp3 sp2 sp

Orbitals to One s, three p One s, two p One s, one p

hybridize
New orbital FOUR sp3 THREE sp2 TWO sp orbitals
diagram orbitals orbitals (2 p orbitals
(1 p orbital unhybridized)
unhybridized)
Types of bonds 4 sigma 3 sigma, 1 pi 2 sigma, 2 pi
formed
Bond angles 109.5 120 180
Shape Tetrahedral Trigonal planar Linear
SLRM2020
TOPIC: Bonding and hybridization
What is the total number of sigma bonds found in the
following compound?

A) 8
B) 10
C) 11
D) 15
SLRM2020
TOPIC: Bonding and hybridization
Which of the following properly describes all the
carbons in benzene?
A) display tetrahedral geometry
B) has purely sp2-sp2 orbital overlaps
C) can hold two sigma bonds
D) can hold two pi bonds
E) has bond angles of 180 degrees
SLRM2020
TOPIC: Intermolecular forces (influence on Tb/Tm)
Which would have the highest boiling point?
A)

B) C)

D)
SLRM2020
TOPIC: Intermolecular forces (influence on density)
Which of the following compounds is expected to have
the highest density?

SLRM2020
TOPIC: Intermolecular forces (influence on solubility)
Arrange from least to most water soluble
A) Toluene < methanol < acetone
B) Methanol < toluene < acetone
C) Toluene < acetone < methanol
D) Methanol < toluene < acetone

SLRM2020
TOPIC: Intermolecular forces (influence on solubility)
Imagine that you have an experiment where you have to
extract polyphenols from a leaf extract. Polyphenols include
flavonoids and tannins.

If in the lab you have solvents diethyl ether (A), hexane (B), or
ethanol (C), which hypothetically extracts the most tannins?

SLRM2020
TOPIC: Structural effects (electron delocalization)
What hybridization is required to achieve
resonance?
A) s
B) sp
C) sp2
D) sp3

SLRM2020
For a compound to be considered aromatic, it must have the
following characteristics:
I. planar and cyclic II. sp3 hybridization
III. follows the 4n + 2 rule IV. cumulated double bonds
A) I, IV
B) I, III
C) I, II, III, IV
D) I, II, III

JPJ2020
TOPIC: Structural effects (inductive effects)
Which of the following processes increases the
stability of a carbon?
A) lack of surrounding carbons
B) electron delocalization
C) steric hindrance
D) electronegative atoms
SLRM2020
ANSWER
TOPIC: Aromatic compounds

A) Aromatic
B) Not aromatic
C) Anti-aromatic
D) Aliphatic
JPJ2020
TOPIC: Structural effects (inductive effects)
Which of the following alkyl halides has the most
stable alpha carbon?
A) ethyl chloride
B) 1-chloropropane
C) 2-chloropropane
D) chloromethane
SLRM2020
SLRM2020
TOPIC: Isomers (constitutional)
Which of the following pairs of compounds are NOT
constitutional isomers?
A) butanol and diethyl ether
B) glucose-1-phosphate and glucose-6-phosphate
C) 2-methylbutane and pentane
D) R-warfarin and S-warfarin

SLRM2020
TOPIC: Isomers (configurational)
Which of the following is most appropriately called a
trans-isomer?

A) B)

C) D)
SLRM2020
PRACTICE: OPTICAL ISOMERS

NOTE
Whether a
compound is
assigned (R)
or (S) does
NOT equate to
their dextro-
or levo- spin!
TOPIC: Isomers (configurational)
Give the proper descriptor for this particular isomer of
the amphetamine structure shown:

A) R
B) S
SLRM2020
TOPIC: Basics of organic reactions
An electron poor species:
A) Nucleophile
B) Electrophile
C) Radical
D) Lewis Base

JPJ2020
TOPIC: Basics of organic reactions
The reaction below is an example of

A) Addition C) Elimination
B) Substitution D) Rearrangement

SLRM2020
Which of the following functional group transformations is a
reduction reaction?

A) Conversion of an aldehyde to a carboxylic acid

B) Conversion of a carboxylic acid to CO2
C) Conversion of alcohol to an aldehyde
D) Conversion of a ketone to an alcohol
E) Conversion of an alkene to an alcohol
SLRM2020
TOPIC: Alkanes, alkenes, and alkynes
The addition of water to alkene must be carried out in
what environment?
A) Basic
B) Neutral
C) Acidic
D) Cold

JPJ2020
TOPIC: Alkanes, alkenes, and alkynes
The reaction of alkene with chlorine gas in the presence
of carbon tetrachloride produces:
A) Alkyl Halide
B) Vicinal Dihalide
C) Alcohol
D) Vicinal Diol

JPJ2020
TOPIC: Alkanes, alkenes, and alkynes
What is the likely product after this reaction?

A B

C D
JPJ2020
TOPIC: Alkanes, alkenes, and alkynes
What will be the product in this reaction?

A) Alkene B) Alcohol
C) Carboxylic acids D) Alkane

JPJ2020
TOPIC: Alkanes, alkenes, and alkynes
Which of the following is the highest possible product
when an enol tautomerizes?
A) Aldehydes
B) Carboxylic acids
C) Alcohols
D) Enals

JPJ2020
TOPIC: Aromatic compounds
Methylbenzene is also known as:
A) Aniline
B) Toluene
C) Anisole
D) Catechol

JPJ2020
TOPIC: Reactions of benzene
Which of the following requires sulfuric acid as a
catalyst?
A) Alkylation of benzene
B) Sulfonation of benzene
C) Nitration of benzene
D) A and B
E) B and C
JPJ2020
TOPIC: Alcohols and ethers
This is the structure of ethambutol. What is the
classification of its alcohol portions?

A) Primary
B) Secondary
C) Tertiary
D) Quaternary

SLRM2022
TOPIC: Alcohols and ethers
What is the formula of the product formed from
oxidation of isopropyl alcohol?
A) RCOOR
B) RCHO
C) RCOOH
D) ROR
E) RCOR
 ANSWER
TOPIC: Alcohols and ethers
What is the product of the reaction of a tertiary alcohol
with potassium dichromate?
A) Aldehyde
B) Alcohol
C) Ketone
D) Carboxylic Acid

JPJ2020
TOPIC: Alcohols and ethers
Which of the following is the most logical starting material
for ether synthesis?
A) olefin
B) alcohol
C) alkyl halide
D) arene

SLRM2022
TOPIC: Aldehydes and ketones
Which of the following functional groups is present in
both aldehydes and ketones?
A) Carbinol
B) Carbonyl
C) Carboxyl
D) Hydroxyl

CLC2020
TOPIC: Reactions of carbonyl compounds
When acetone is reacted with Grignard reagent, it
turns into a
A) Carboxylic acid
B) Primary alcohol
C) Secondary alcohol
D) Tertiary alcohol
E) None of the above

CLC2020
TOPIC: Reactions of carbonyl compounds
Tollen’s reagent (Ag+) is an oxidizing agent. What are the
products of Tollen’s reagent with the following
molecule
A) Propanol and Ag+
B) Propanoic acid and Ag+
C) Propanol and Ag
D) Propanoic acid and Ag

CLC2020
TRIVIAL NAMES FOR CARBOXYLIC ACIDS
NO. OF CARBONS MONOCARBOXYLIC DICARBOXYLIC
1 Formic N/A
2 Acetic Oxalic
3 Propionic Malonic
4 Butyric Succinic
5 Valeric Glutaric
6 Caproic Adipic
7 Enanthic Pimelic
8 Caprylic Suberic
9 Pelargonic Azelaic
10 Capric Sebacic
TOPIC: Carboxylic acids and their derivatives

is the general formula for:

A) Esters
B) Amides
C) Anhydrides
D) Acid halides
CLC2020
TOPIC: Carboxylic acids and their derivatives
What is the IUPAC name of the
following compound?

A) 1-propylbutanoic acid
B) heptane-4-oic acid
C) 2-propylpentanoic acid
D) 3-pentylpropanoic acid
SLRM2023
TOPIC: Carboxylic acids and their derivatives
Which of the following is pentyl ethanoate?

A C

B D
CLC2020
TOPIC: Carboxylic acids and their derivatives
The product of the reaction of a carboxylic acid and an
alcohol
A) Ketone and water
B) Aldehyde and water
C) Acid chloride and water
D) Ester and water

CLC2020
TOPIC: Carboxylic acids and their derivatives
Base-mediated ester hydrolysis
A) Esterification
B) Saponification
C) Resinification
D) Rancidification

CLC2020
TOPIC: Carboxylic acids and their derivatives
What is the product of the following reaction?

A) Propane D) Propan-1-ol
B) Propanone E) Propan-2-ol
C) Propanal
CLC2020
TOPIC: Carboxylic acids and their derivatives
Which of the following reactions are ways to synthesize
carboxylic acids?
I. Oxidation of an aldehyde
II. Hydrolysis of an anhydride
III. Hydrolysis of a ketone
A) I
B) I and II
C) II and III
D) I and III
CLC2020
TOPIC: Amines
Which of the following is a primary amine?
A) Aniline
B) Anisole
C) Anthracene
D) Adrenaline

CLC2020
TOPIC: Carboxylic acids and their derivatives
What is the IUPAC name of the compound shown?

A) N-butylethanamide
B) N-methylpropanamide
C) N-butylformamide
D) N-methylbutanamide
E) 1-methylpropanamide
CLC2020
TOPIC: Amines
Which of the following statements about amines is
incorrect?
A) They react with acids to form salts
B) Aliphatic amines are more basic than aromatic
amines
C) Primary amines are more basic than secondary
amines
D) Amines are supposed to have high pKa values
CLC2020
Nitric acid is likely to colorize and detect

A) alcohols
B) alkenes and unsaturations
C) carbonyl groups
D) aromatic rings
Which of the following will form a precipitate with
dinitrophenylhydrazine?

A) propionic acid
B) acetone
C) butene
D) isobutyl alcohol
E) two of the choices
The IR spectrum of a sample shows narrow peaks
around 3300 cm-1. Proton NMR shows multiple peaks
at around 7.0 ppm. Furthermore, subjecting the sample
to benzenesulfonyl chloride yielded a precipitate. From
the choices, which is the likely sample?
A) tert-butyl alcohol
B) ethanal
C) aniline
D) trimethylamine