CHEM 219 ORGANIC CHEMISTRY MODULE
5 CERTIFICATION SCRIPT 2026 QUESTIONS
WITH SOLUTIONS GRADED A+
◍ 1. D2. A3. B4. C.
Answer: Using the date from the following tables, do the following: Match
each crown ether to the correct structural formula
◍ Sideways orbital overlap.
Answer: - associated with P orbitals only- Pi orbital
◍ a. 3b. 8.
Answer: For the following molecule, determine:a. The number of
stereocenters present.b. The maximum number of individual stereoisomers
that could possibly exist for the compound.
◍ i. Aromaticii. Cycliciii. Ether, Benzene (Aromatic) Ring.
Answer: Classify the following organic molecule in terms of:i) The type of
hydrocarbon skeletonii) The configuration of the hydrocarbon skeleton
(linear, branched, or cyclic)iii) The type of functional group(s) present -
name all the groups present (include subclassification of 1°, 2°, 3° when
appropriate). You are not being asked to generate the IUPAC name of the
molecule, only to state what functional groups are present.
◍ VSEPR: Trigonal planar 120 degrees.
Answer: 3 bonding, 0 lone pairs= 3 total
◍ 1. Unlikely2. Likely3. Likely4. Unlikely.
Answer: Based on the reactivity trend for carboxylic acid derivatives, state
whether the following conversions are likely to occur (or not):1. Amide to
Ester2. Acid Anhydride to Amide3. Acid Anhydride to Ester4. Amide to
Ester
,◍ False.
Answer: Determine if the following statement regarding aromatic
compounds is true or false.As a class, aromatic molecules are referred to as
“arsoles”.
◍ False.
Answer: Determine if the following statements regarding substitution (Sn)
and elimination (E) mechanisms are true or false.The use of weak bases as
nucleophiles promotes elimination over substitution in most cases.
◍ True.
Answer: Determine if the following statement regarding aromatic
compounds is true or false.The π-bonding network in the benzene ring is
formed by the side-by-side overlap of p orbitals located on each carbon of
the ring.
◍ True or False: Moving double bonds in electron resonance is not allowed, as
that would change the connectivity of the atom in the molecule?.
Answer: False
◍ On a piece of scrap paper, draw the resonance structure "b" that would result
from redistributing the electrons as shown on structure "a" in the diagram
below:For your structure "b", complete the table with the information
requested:.
Answer: Oxygen: 1 lone pair, 1 single bond, 1 double bond, +1 formal
charge.Carbon (1): 0 lone pair, 2 single bond, 1 double bond, 0 formal
charge.Carbon (II): 1 lone pair, 3 single bond, 0 double bond, -1 formal
charge.
◍ VSEPR: Tetrahedral 109.5 degrees.
Answer: 4 bonding pairs, 0 lone pairs= 4 total
◍ Classify the bonding between the given pairs of atoms as ionic, covalent, or
polar covalent. Use the table of electronegativities shown below to help with
the classification.a. Br and Brb. K and Clc. P and Cld. C and Oe. Na and Br.
Answer: a. Br-Br: Electronegativity difference () = 0 = COVALENT (or
, pure covalent)b. K-Cl: () = 2.2 = IONICc. P-Cl: ()= 0.9 = POLAR
COVALENTd. C-O: ()= 1.0 = POLAR COVALENTe. Na-Br: () = 1.8 =
POLAR COVALENT
◍ Using the VSEPR method, predict the molecular geometry (shape and bond
angle) around the indicated atoms for the following structure:a) C(I) b)
C(II)c) Nd) S.
Answer: a) C(I) = 4 bond pairs = TETRAHEDRAL, 109.5°b) C(II) = 3 bond
pairs = TRIGONAL PLANAR, 120°c) N = 3 bond pairs/1 lone pair =
TRIGONAL PYRAMIDAL, 107°d) S = 2 bond pairs/2 lone pairs =
ANGULAR/BENT, 105°
◍ True.
Answer: Determine if the following statement regarding aromatic
compounds is true or false.Two substituents located on carbons 1 and 4 of
the benzene ring are said to be para to each other.
◍ False.
Answer: Determine if the following statement regarding aromatic
compounds is true or false.The π-bonding network in the benzene ring is
formed by the end-on overlap of p orbitals located on each carbon of the
ring.
◍ Cation.
Answer: Becomes positively charged when it loses an electron
◍ The structural formula:Has what molecular formula?a. C7H16 b. C6H14 c.
C7H14 d. C6H12 e. C7H12.
Answer: (c)
◍ A resonance double-headed arrow points to where the electrons being
redistributed begin..
Answer: Falsejust connects resonance structures and show that the electronic
structure is a hybrid of those forms
◍ C8H10.
Answer: Determine the molecular formula for the given structural formula
5 CERTIFICATION SCRIPT 2026 QUESTIONS
WITH SOLUTIONS GRADED A+
◍ 1. D2. A3. B4. C.
Answer: Using the date from the following tables, do the following: Match
each crown ether to the correct structural formula
◍ Sideways orbital overlap.
Answer: - associated with P orbitals only- Pi orbital
◍ a. 3b. 8.
Answer: For the following molecule, determine:a. The number of
stereocenters present.b. The maximum number of individual stereoisomers
that could possibly exist for the compound.
◍ i. Aromaticii. Cycliciii. Ether, Benzene (Aromatic) Ring.
Answer: Classify the following organic molecule in terms of:i) The type of
hydrocarbon skeletonii) The configuration of the hydrocarbon skeleton
(linear, branched, or cyclic)iii) The type of functional group(s) present -
name all the groups present (include subclassification of 1°, 2°, 3° when
appropriate). You are not being asked to generate the IUPAC name of the
molecule, only to state what functional groups are present.
◍ VSEPR: Trigonal planar 120 degrees.
Answer: 3 bonding, 0 lone pairs= 3 total
◍ 1. Unlikely2. Likely3. Likely4. Unlikely.
Answer: Based on the reactivity trend for carboxylic acid derivatives, state
whether the following conversions are likely to occur (or not):1. Amide to
Ester2. Acid Anhydride to Amide3. Acid Anhydride to Ester4. Amide to
Ester
,◍ False.
Answer: Determine if the following statement regarding aromatic
compounds is true or false.As a class, aromatic molecules are referred to as
“arsoles”.
◍ False.
Answer: Determine if the following statements regarding substitution (Sn)
and elimination (E) mechanisms are true or false.The use of weak bases as
nucleophiles promotes elimination over substitution in most cases.
◍ True.
Answer: Determine if the following statement regarding aromatic
compounds is true or false.The π-bonding network in the benzene ring is
formed by the side-by-side overlap of p orbitals located on each carbon of
the ring.
◍ True or False: Moving double bonds in electron resonance is not allowed, as
that would change the connectivity of the atom in the molecule?.
Answer: False
◍ On a piece of scrap paper, draw the resonance structure "b" that would result
from redistributing the electrons as shown on structure "a" in the diagram
below:For your structure "b", complete the table with the information
requested:.
Answer: Oxygen: 1 lone pair, 1 single bond, 1 double bond, +1 formal
charge.Carbon (1): 0 lone pair, 2 single bond, 1 double bond, 0 formal
charge.Carbon (II): 1 lone pair, 3 single bond, 0 double bond, -1 formal
charge.
◍ VSEPR: Tetrahedral 109.5 degrees.
Answer: 4 bonding pairs, 0 lone pairs= 4 total
◍ Classify the bonding between the given pairs of atoms as ionic, covalent, or
polar covalent. Use the table of electronegativities shown below to help with
the classification.a. Br and Brb. K and Clc. P and Cld. C and Oe. Na and Br.
Answer: a. Br-Br: Electronegativity difference () = 0 = COVALENT (or
, pure covalent)b. K-Cl: () = 2.2 = IONICc. P-Cl: ()= 0.9 = POLAR
COVALENTd. C-O: ()= 1.0 = POLAR COVALENTe. Na-Br: () = 1.8 =
POLAR COVALENT
◍ Using the VSEPR method, predict the molecular geometry (shape and bond
angle) around the indicated atoms for the following structure:a) C(I) b)
C(II)c) Nd) S.
Answer: a) C(I) = 4 bond pairs = TETRAHEDRAL, 109.5°b) C(II) = 3 bond
pairs = TRIGONAL PLANAR, 120°c) N = 3 bond pairs/1 lone pair =
TRIGONAL PYRAMIDAL, 107°d) S = 2 bond pairs/2 lone pairs =
ANGULAR/BENT, 105°
◍ True.
Answer: Determine if the following statement regarding aromatic
compounds is true or false.Two substituents located on carbons 1 and 4 of
the benzene ring are said to be para to each other.
◍ False.
Answer: Determine if the following statement regarding aromatic
compounds is true or false.The π-bonding network in the benzene ring is
formed by the end-on overlap of p orbitals located on each carbon of the
ring.
◍ Cation.
Answer: Becomes positively charged when it loses an electron
◍ The structural formula:Has what molecular formula?a. C7H16 b. C6H14 c.
C7H14 d. C6H12 e. C7H12.
Answer: (c)
◍ A resonance double-headed arrow points to where the electrons being
redistributed begin..
Answer: Falsejust connects resonance structures and show that the electronic
structure is a hybrid of those forms
◍ C8H10.
Answer: Determine the molecular formula for the given structural formula
