CHEM 33

W ee N e ca e

Name he c e belo o p o ide hei d a ing.

1.

2. 4-e h n lc clohe -1- ne

3.

4. 4-nonen-3,7-dione

5.

6.
CHEM 33
W ee N e ca e

7.

8.
CHEM 33
W ee N e ca e
ANSWER KEY

1. bic clo [4,3,1] decane

2.

3. 6-e h l-3,4-dime h loc ane

4.

5. 5-e h l-7-(1,2-difl o ob l) idecane

6. me h l in l ke one

7. 2,4-dini o ol ene

8.5-chlo o-4-me h lhep an-3-one

 Worksheet - Hybridization

When atoms bond to form molecules, they use molecular orbitals. These are
formed through the hybridization of the atomic orbitals that we have already
discussed, s, p, and d orbitals.

The hybridized molecular orbitals have different shapes and energy levels
than the atomic orbitals. The number of molecular orbitals created by
hybridization depends on the number of atomic orbitals that are mixed to form
them.

In forming sp3 hybridized orbitals, four atomic orbitals are mixed, one s and three
p. The energy diagram for this process is shown below. The hybridized orbitals
are higher in energy than the s orbital, but lower in energy than the p orbitals.

p
energy
sp3
s hybridization

atomic orbitals hybridized orbitals

Carbon has 4 valence electrons. Add these electrons to the atomic and
molecular orbitals. This hybridization gives tetrahedral geometry.

With this hybridization, C will form four equivalent σ bonds.

Draw a similar energy diagram for sp3 hybridized oxygen.

How many σ bonds will be formed?

How are the other sp3 orbitals used?

Do the same for sp3 hybridized nitrogen.

In some Lewis structures, there are only three equivalent bonds formed. To
create three equivalent hybridized orbitals, mix three atomic orbitals.

Draw and name the orbitals formed in this hybridization, then add the electrons
for sulfur. Since the hybridized orbitals are close in energy, every orbital is filled
with one electron before electrons are paired.

p
energy

s hybridization

The hybridized orbitals will form σ bond(s).

The unhybridized orbital will form π bond(s).

There will be lone pair(s).

This hybridization gives trigonal planar geometry.

In linear molecules, like CO2, the central atom has only two equivalent bonding
orbitals. Draw the energy levels and name the orbitals formed in this
hybridization.

p
energy

s hybridization

Fill in the electrons for carbon and determine the number and typed of bonds
formed.

In CO2, determine the hybridization of the oxygen atoms. Complete the energy
diagram for the oxygens. Draw the structure of CO 2.

p
energy

s hybridization
In atoms with n=3 or larger, the d orbitals can also be hybridized. In molecules
with five molecular orbitals, five atomic orbitals are mixed:

+ + + +

This will give trigonal bipyramidal geometry and is called dsp3 hybridization.

Finally, molecules with octahedral geometry, will have molecular orbitals.

This hybridization is called .

Shown below is a portion of the chart from Worksheet 13. Fill in the
hybridization for each of the compounds.

compound bonds lone geometry shape hybridization

pairs

SF6 6 0 octahedral octahedral

NH3 3 1 tetrahedral trigonal

pyramidal

ICl4- 4 2 octahedral square

planar

CF4 4 0 tetrahedral tetrahedral

SO3 3 0 trigonal trigonal

planar planar

SF4 4 1 trigonal seesaw

bipyramidal

CO2 2 0 linear linear

H2O 2 2 tetrahedral V-shaped

NO2- 2 1 trigonal V-shaped

planar
 The molecule shown to the left is riboflavin
(vitamin B2). Answer the following questions
about its structure.

a) how many carbons are sp3 hybridized?

sp2 hybridized?

sp hybridized?

b) How many nitrogens are sp3 hybridized?

sp2 hybridized?

sp hybridized?

c) How many oxygens are sp3 hybridized?

sp2 hybridized?

sp hybridized?

d) How many σ bonds are there in total?

e) How many π bonds are there in total?

f) Which of the three rings are planar?

The acetate ion, C2H3O2- , has both oxygens bonded to the same carbon.

a) Draw the Lewis structure and all resonance forms.

b) Label the hybridization around each carbon.

c) Pick one resonance structure and label the hybridization of each oxygen.

d) How many σ and π bonds are present?

e) Which atom carries the formal negative charge?

ANSWERS
Stereogenic Centers
- Stereogenic center: ​tetrahedral​ atoms with 4 ​different​ substituents
- Oftentimes a carbon atom, but may also include other elements like
nitrogen and phosphorus
- Carbon atoms with pi bonds are automatically disqualified
- All chiral molecules have stereogenic centers, but not all molecules with
stereogenic centers are chiral
- Chiral center: stereogenic center of a chiral molecule
- Exchanging two groups attached to a chiral center changes the molecule
into a different stereoisomer

Exercises:

I. Determine whether the following ​organic compounds are ​chiral ​or achiral ​(no
chiral centers). If it is chiral, ​identify the stereogenic centers in the structural
formulas presented below.
II. Identify​ the chiral stereogenic centers in the structural formulas presented below.

1.
4.

2.

5.

3.
Answer Key:

I.

*Organic Compounds F and G are achiral so they do not have a stereogenic center/s.

II.

1. 4.

2.

5.

3.
Additional Resources

https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Or
ganic_Chemistry)/Chirality/Stereoisomers/Chirality_and_Symmetry/Enantiomorphism/Pr
actice_Problems

https://www.masterorganicchemistry.com/organic-chemistry-practice-problems/stereoch
emistry-practice-problems-and-quizzes/

https://apps-dso.sws.iastate.edu/si/documentdb/spring_2011/CHEM_331_Trahanovsky
_ericasbe_Chem_331_Worksheet_15_Key.pdf

http://leah4sci.com/chirality-and-stereochemistry-practice-quiz/
VALENCE BOND THEORY WORKSHEET

1. Complete the table below.

Compound Lewis Structure Hybridization of Number of sigma Number of pi

Central Atom bonds bonds
CH4

N2

SF6

2. What characteristic must the atomic orbitals involved in a bond have? “c”
a. They must have two electrons.
b. They must be p orbitals.
c. They must have one electron.
d. They must be s orbitals.

3. During the formation of a HCl molecule, the ___ orbital of hydrogen overlaps with the ___ orbital of
chlorine.
4. True or False

5. Covalent bonds are formed by _____ of atomic orbitals, each of which contains one electron of _____
the same spin.
VALENCE BOND THEORY WORKSHEET

6-8. Overlapping orbitals are like overlapping waves.

In __________ In __________
Interference, waves that Interference, waves are
are in phase will combine out of phase and cancel
each other and increase each other out. This does
the ________. This is the not result in a bond.
only interference that
results in a bond.

____ is a point where

there is no chance of
finding an electron.
VALENCE BOND THEORY WORKSHEET

Key to correction:
1. Complete the table below.
Compound Lewis Structure Hybridization of Number of sigma Number of pi
Central Atom bonds bonds
1. CH4 sp3 4 0

2. N2 sp 1 2

3. SF6 sp3 d2 6 0

2. C
3. 1s; 3p
4. False
5. Overlap; opposite
6-8. Overlapping orbitals are like overlapping waves.

In constructive interference, In destructive interference,

waves that are in phase will waves are out of phase and
combine each other and cancel each other out. This
increase the amplitude. This does not result in a bond.
is the only interference that
results in a bond.
VALENCE BOND THEORY WORKSHEET

Node is a point where

there is no chance of
finding an electron.
QUESTIONS

1. A Lewis structure for sulfur hexafluoride, SF​6​, is shown. Which statement is

correct concerning this molecule?

A. The octet rule is obeyed completely in this Lewis structure.

B. The central sulfur atom shows an expanded valence-shell octet common in
Period 3 elements.
C. The central sulfur atom in this Lewis structure shows an impossibly high
oxidation state.
D. Oxygen can form a similar and more stable hexafluoride.
E. This Lewis structure is a poor illustration of the actual electron distribution for this
molecule.

2. For the compounds CH​3​Cl, CH​3​Br, CH​3​I, and CH​3​F, the correct order of
increasing C-halogen bond length is:

A. CH​3​F < CH​3​Cl < CH​3​Br < CH​3​I

B. CH​3​F < CH​3​Br < CH​3​Cl < CH​3​I
C. CH​3​F < CH​3​I < CH​3​Br < CH​3​Cl
D. CH​3​Cl < CH​3​Br < CH​3​F < CH​3​I
3. Draw a correct Lewis structure for boric acid, B(OH)3.

4. What kind of molecular orbital (sigma or pi) results when the two atomic
orbitals shown below approach each other sideways as indicated?

5. Identify the more polar bond in each of the following pairs of bonds:
a. HF or HCl
b. NO or CO
c. SH or OH
d. PCl or SCl

6. Which of the following statements describe the difference between a sigma (σ)
and a pi (π) bond?

A. Pi (π) bonds form a side-to-side overlap of hybridized sp, sp​2​, or sp​3​ orbitals.
B. Sigma (σ) bonds form the end-to-end overlap of two hybridized s or p orbitals.
C. The maximum number of sigma (σ) versus pi (π) bonds between atoms are
different but their energy levels are the same.
D. Only sigma (σ) bonds use hybridized orbitals to overlap in forming the bond.
7. The diagram below shows the electron arrangements of magnesium and
oxygen:

a. Draw a diagram showing how a bond is made between magnesium and

oxygen.
b. What name is given to this type of chemical bond?

8. Which of the following statements would cause a covalent bond to form?

A. Two atoms share electrons so they can fill their outer shells
B. A hydrogen atom with a slight positive charge is attracted to a negative charge of
another molecule or atom
C. One atom loses one or more electrons and the other atom gains one or more
electrons
D. The constant motion of electrons and the creation of charge imbalances bonds
two molecules together
ANSWERS

1. B
2. A
Explanation: C-halogen bond length totally depends on the electronegativity difference
between Carbon and halogen. The more the difference is, the less is the bond length.
The electronegativity order of halogens is I<Br<Cl<F. Hence, the correct order of
increasing C-halogen bond length is CH​3F​ < CH3​ Cl
​ < CH3​ ​Br < CH​3​I

3.
4. Pi
5. a. ​HF
b. CO
c. OH
d. PCl
6. D

7. a.
b. Ionic
8. A
CHEM33 LEC [TRANS]
HYBRIDIZATION
➢ The combination of pure atomic orbitals to form hybrid orbitals.
➢ The name of the orbital comes from the number of pure orbitals which comprise it.
○ sp = s + p
○ sp​2​ = S + p + p
○ sp​3 ​= s + p + p + p
○ sp​3​d = s + p + p + p + d
○ sp​3​d​2​ = s + p + p + p + d + d
➢ The type of hybrid orbital formed dictates the shape or molecular geometry of the
molecule.

Hybridization
State

sp

sp​2

sp​3

sp​3​d

sp​3​d​2

REMEMBER: ​The steric number is the number of atoms bonded to the central atom. Memorize
the corresponding hybridization state of the steric number! PERFECT MO NA QUIZ N’YAN.

The five basic shapes of hybridization are linear, trigonal planar, tetrahedral, trigonal
bipyramidal, and octahedral.
The geometry of the orbital arrangement:

● Linear: Two electron groups involved resulting in sp hybridization, the angle between the
orbitals is 180°.
● Trigonal planar: Three electron groups involved resulting in sp2 hybridization, the angle
between the orbitals is 120°.
● Tetrahedral: Four electron groups involved resulting in sp3 hybridization, the angle
between the orbitals is 109.5°.
● Trigonal bipyramidal: Five electron groups involved resulting in sp3d hybridization, the
angle between the orbitals is 90°, 120°.
● Octahedral: Six electron groups involved resulting in sp3d2 hybridization, the angle
between the orbitals is 90°.

Valence Bond Theory​ - two atoms should share one electron each to form covalent bonds
- proposes that atomic orbitals undergo orbital hybridization to satisfy the structural
requirements of a molecule

Valence Share Electron Repulsion (VSEPR Theory) ​- valence electrons (bonded and lone
pairs) repel each other
Sigma (𝝈) bond​ provides maximum head on overlap
Pi (𝛑) bond​ - unhybridized p orbital, created by side by side orbital overlap

The ​𝝈 bond is always the ​first type of bond to form and is also the ​stronger one​, rather ​than the
𝛑 bond​. Moreover, unless a pair of atoms forms a sigma bond, there can be no pi bond
between them. Therefore, if a pair of atoms are held together by a single bond only, that must
be a sigma bond. Pi bonds are present only in cases of double and triple bonds.

C −C 1 bond
C ＝C 1 bond and 1 bond ​**Double bonds cannot rotate freely; otherwise, the pi bond will break.
CC 1 bond and 2 bond
 WORKSHEET

1. In the molecule ​caffeine, ​identify the hybridization states of all nitrogen atoms.

2. Identify the hybridization states of the carbon atoms in the glucose molecule below.

3. What is the hybridization state of sulfur in sulfur tetrachloride (SF​4​)?

4.Identify the hybridization state:

5. ​Acrylonitrile is a colorless, volatile liquid with a pungent, onion-like odor. Acrylonitrile is widely
used in industry to produce rubber, resins, plastics, elastomers and synthetic fibers and to
manufacture ​carbon fibers used in aircraft, defense and aerospace industries. ​What is the
Hybridization state of the carbon atom 1 in the molecule? Identify the number of 𝝈 bond and 𝛑
bond.
6. What is the hybridization state of bromine in bromine pentafluoride (​BrF​5​)?

7. Identify the hybridization state of the numbered atoms.

ANSWERS
1. All of the nitrogen atoms in the molecule caffeine is in sp​2 ​hybridization state. Take note
that the lone pair present in nitrogen 1, 2 and 3 is in the unhybridized p orbital and is part
of the aromatic system. The lone pair of the Nitrogen atom is adjacent to a Carbon atom
with a bond (double bond) so it can delocalize.

2. Carbon atoms are in sp​3 ​hybridization state since they all have four bonded atoms. Note
that there are hydrogen atoms that have been omitted in the bond-line structure. The
molecular formula of glucose is C​6​H​12​O​6

3. The sulfur formed five hybrid orbitals therefore, it is sp​3​d hybridized. The sulfur is bonded
to four chlorine atoms and it also has one lone pair. Remember to draw the lewis
structure of the atoms so you won’t get confused with its valence electrons.

4. a = sp​3​, b = sp​3​, c = sp​2​, d = sp​2​, e = sp​2​, f = sp​2​, g = sp​3​, h = sp​2​, i = sp​3

(Note: Always check the lone pairs that will participate in resonance- e.g. e and h)

5. Carbon atom 1 is in sp hybridization state since it is single bonded to C and triple

bonded to N only, giving the steric number of 2. There are 6 𝝈 bonds and 3 𝛑 bonds.

6. Bromine is in sp​3​d​2 hybridization state since it formed six hybrid orbitals. Five fluorine
atoms and one lone pair are bonded to the bromine.

7. 1 = sp​3​ ; 2 = sp​3​ ; 3 = sp​2​ ; 4 = sp​2 ​; 5 = sp​3​ ; 6 = sp​2 ​; 7 = sp ; 8 = sp​2

1. Bond- Line Structure

- Formula consisting bonds and lines

- Easier and fairly accurate in representing bond angles compared to Lewis structures and
condensed formula
- Zigzag format

2. Drawing Bond Line Structures

• Number of corner or endpoint = number of carbon atoms

• All atoms other than carbon and hydrogen must be drawn.

Double bonds are shown with two lines Triple bonds are shown with three lines

Triple bonds – draw in a straight line than zigzag because they are linear (180°)

CORRECT CORRECT INCORRECT

These structures are similar:

Rule 1:

𝑠𝑝2 and 𝑠𝑝3 hybridized atoms in a straight chain should be drawn in zigzag format.

Rule 2:

Draw other bonds as far away from the double bond as possible.

AVOID THIS!

Rule 3:

The direction in which the bonds are drawn is irrelevant.

THE SAME!

Rule 4:

All heteroatoms (such as nitrogen or oxygen) must be drawn, as well as the H atoms attached to them.
REMEMBER:

1. NEVER draw more than four bonds to a carbon atom (octet rule).
2. Draw all the bonds as far as possible from each other.

Identifying Functional Groups

• Bond-line structures:
o Easier to read
o More obvious to see the changes/transformations

3. Carbon Atoms with Formal Charges

• A carbon atom WITHOUT a formal charge have 4 bonds

• Carbon (+) Carbonation = 3 bonds (and one empty orbital)
• carbanion = three bonds, but also a lone pair. (no empty orbitals)
• Formal charge affects the stability and reactivity of molecules
• you need to be able to identify formal charges in bond line representations

4. Bond-line structures: identifying lone pairs

• Formal charge must ALWAYS be drawn, but it is optional if you want to include lone pairs
• The presence or absence of lone pairs is connected to the formal charge
Oxygen has THREE possible bonding patterns.

The formal charge on a N atoms can be calculated the same way or by matching its bonding pattern with
its formal charge

5. Bond-Line Structures: Formal Charges

For some molecules, not every atom can have its preferred number of bonds and lone electron pairs.
Formal charge can be a useful concept in determining the most likely Lewis structure for a compound. In
general, preferred structures will have minimised formal charges on each atom.

In order to calculate the formal charge of an atom in a molecule, three things must be determined:

• the number of valence electrons of the element

• the number of electrons that the atom has in lone pairs
• the number of electrons that the atom shares in bonds

Formal charge can be calculated by the following formula:

Formal charge = (valence electrons) – (lone pair electrons) – 1⁄2 (shared electrons)

A negative formal charge means that an atom has more electrons than it does in atomic form,
while a positive formal charge means that it has fewer electrons.

4. Bond-Line Structures in 3-D

• Bond-line structures can be used to represent a 3D molecule in a 2D piece of paper.

• Since molecules are 3-dimensional (3D) structures so it is always more accurate to describe
them in 3D.
• sketching molecules in 3D can help in identifying different information of the molecules.
(bond angles, shapes of molecules and its isomers)
NOTE! The shape of a compound governs how it interacts biologically, and so it is important to
accurately depict and interpret 3-D in bond-line structures.

Here are the types of bonds used in drawing 3D molecular structures:

a) Normal lines (or normal bonds) are used to represent
covalent bonds lying in the plane of the drawing
surface.
b) Dashed bonds are used to represent covalent bonds
projecting towards the viewer. (project backward)
c) Wedged bonds are used to represent covalent bonds
projecting away from the viewer.
(project outward/ forward)

Examples:

A simple example of a 3D Structural Formula is that for methane, whose molecular formula is CH4

The sketched 3D structural formula of methane (on

the left) may be understood even more clearly by
comparison with the ('ball and stick') model of the
3D structure of methane (on the right).

Other ways to show 3-D structure

a) Fischer Projection (acyclic compounds)
- horizontal lines represent bonds projecting from the plane of
the paper toward the viewer, and vertical lines represent bonds
projecting away from the viewer.

b) Haworth Projection (cyclic compounds)

- takes the simplicity of a hexagon while keeping some of the
important aspects of the molecule such as the direction that
the attachments are oriented on the molecule.
Questions:
A)
5.)
1.)

a.) How many Hydrogen atoms?

b.) How many Carbon atoms? c.) How many Hydrogen atoms?
d.) How many Carbon atoms?
2.)

B) Convert into bond-line structures:

1. 𝐶𝐻3 𝐶𝐻𝐶𝐻𝑁(𝐶𝐻3 )𝐶𝐻2 𝐶𝐻3
2. 𝐶𝐻3 𝐶𝐻𝐶𝐻𝐶𝐻2 𝐶𝐻𝐶𝐻2
a.) How many Hydrogen atoms? 3. 𝐶𝐻3 (𝐶𝐻2 )3𝐶𝐻(𝐶𝐻3 )(𝐶𝐻2 )2 𝑂𝐶𝐻2 𝐶𝐻3
b.) How many Carbon atoms?

3.) C) For the following Lewis structures,

determine the formal charge of each atom.

a.) How many Hydrogen atoms?

b.) How many Carbon atoms?

4.)

a.) How many Hydrogen atoms?

b.) How many Carbon atoms?
Answer Key
A)
1.) a.) 4
b.) 3
2.) a.) 6
b.) 6
3.) a.) 8
b.) 6
4.) a.) 8
b.) 3
5.) a.) 5
b.) 5

B) Answers:

1.

2.

3.

C)
Configuration using the Cahn-Ingold-Prelog System (R and S designation)

Proponents: Robert Cahn, Christopher Ingold at Vladimir Prelog, sila sisihin nyo.

Anyway, the Cahn-Ingold-Prelog (CIP) system involves assigning priorities to the four groups
attached to the chiral center. Bakit kailangang gawin yon? Kasi diba the difference in
enantiomers is only the way they are arranged in space, they needed the CIP to differentiate
enantiomers from each other.

Origin of terms

R - latin word ​rectus​ meaning right

S - latin word ​sinister​ meaning left

Mnemonics:
R = right = clockwise
S = ​sinister​ = counter clockwise kasi nakakatakot pag baliktad na takbo ng clock

How to name

Case 1: Four distinct substituents

1. Number the substituents 1-4 in decreasing atomic number

2. Rotate the molecule such that the fourth priority is on a dash

3. Observe the direction of the sequence 1-2-3, see if it is clockwise or counter-clockwise

 4. Designate R for clockwise and S for counter-clockwise

Case 2: With homogeneous substituents

It is more common to encounter two or more atoms connected to a chiral center having
the same atomic number. For example:

This case has two carbon atoms connected to the chiral center. So pano na to? Iyak
nalang? Of course not, jambo hakdog kaya mo to <3
1. Follow the same step 1 as with the case of four distinct substituents, assign highest (or
lowest) priority to distinct substituents. In the case of the example assign 1 to the OH
group and 4 to the H
2. In order to assign the priorities to the two carbon atoms connected to the chiral center,
we must first remember that besides the chiral center, both carbon atoms are connected
to 3 other atoms. List those 3 atoms in decreasing atomic number

3. In case of a tie, move farther away from the chiral center until the tie is broken

It is important to note that we are looking for the first point of difference, and that we are
assigning based on which has the higher atomic numbers, and not of which has the
higher sum total of lists. As seen below, the left side has higher priority because oxygen
(8) has higher atomic number than carbon (6).

4. In the case of double bonds, it is considered as two separate single bonds (same logic
with triple bonds, three separate single bonds)
Additive: Rotating the Molecule

Mahirap magrotate na walang actual model pero few tips lang siguro?

Example:

What to do with this

Pwede rin if di parin mavisualize, use your fingers (utakpusoKAMAYpera)

Examples:

1. 2.
(S)-1-Fluoro-1-Methoxyethane (S)-3,3-dimethyl-1,2-pentadiol

3. 4.
(R)-1-ethoxy-N-ethylethanamine (3S, 4R)-4-amino-3-hydroxyhexan-2-one

Problem sets:

1.

2.
3.

4.

5.
E and Z Designation
The E-Z notation for geometric isomers is used to substitute for the ambiguity of cis-trans
naming. It is more reliable and particularly suited to tri- or tetrasubstituted alkenes, especially
when the substituents are not alkyl groups. Moreover, the cis-trans naming is for alkenes that
are disubstituted and is not reliable when there are more than two substituents in a double
bond.

Origin of terms
E - german word ​entgegen​ meaning “opposite”
Z - german word ​zusammen​ meaning “together”

Mnemonics:
Z - zame zide
E - eppesite

How to name
First, look at what is attached to each end of the double bond and determine which among them
is the higher priority. Take note that you can determine their priority by comparing their atomic
number. The higher the atomic number, the higher the priority.

(Z)-bromo-2-chlorofluoroethene

In this example, on the left side of the double bond, bromine has higher priority than fluorine,
and on the right side, chlorine has higher priority than hydrogen. If the two groups that are
higher in priority are on the same side (Zame Zide), it is notated as a (Z)-isomer.
(E)-bromo-2-chlorofluoroethene

As for this example, on the left side of the double bond, bromine has higher priority than
fluorine, and on the right side, chlorine has higher priority than hydrogen. This example is just
the same from the first one, but their positions are interchanged. If the two groups that are
higher in priority are on different side or opposite to each other(eppesite), it is notated as an
(E)-isomer

Examples:

(2Z,5E)-3-chloro-6-methylocta-2,5-diene
● If you have two or more double bonds, you have to place the number associated with E
or Z beside it.
Problem sets:

1.

2.

3.

4.

5.
Answer keys for r/s:
1. (R)-2-chloropentane
2. (S)-1-Bromo-2-methylbutane
3. (R)-​1-methyl-4-(1-methylethenyl)-cyclohexene
4. (S)-3-methoxy-1-phenylprop-2-en-1-ol

5. (R)-propanol

Answer keys for e/z:

1. (E)-3-methylhept-3-ene
2. (Z)-4,5-dimethyloct-4-ene
3. (E)-5-(1-bromopropyl)-4,6-dihydroxy-3-methoxy-9-oxodec-7-enal
4. (E)-3-(4-hydroxyphenyl)prop-2-enoic acid
5. (Z)-5,9-dimethyl-6-(1,2- dimethylpropyl)dodeca-5-en-2,10- diyne
CHEM 33

Worksheet on Isomerism

Structural Isomerism:

1.​ ​How many structural isomers does C7H16 have? Draw them.

2. Identify which of the following are structural isomers for molecule (a).

3. Determine if the structures below are isomers:

a.
 b.

c.

4. Which of the following is ​not​ a type of structural isomerism?

A. Functional
B. Positional
C. Chain
D. Optical

Conformational Isomerism:

1. Draw the 2 chair conformers of CIS-1,3-dibromocyclohexane and determine which of the 2

conformers is the most stable.

2. Draw the Conformational Analysis of Propane and identify which is more stable.
3. Draw the most stable conformation of trans-1-tert-butyl-3-ethylcyclohexane.

4. Choose the correct potential-energy diagram for rotation about the C-2−C-3 bond of pentane
through 360∘, starting with the least stable conformer.
 Answer sheet:

Structural Isomerism:

1.​ ​How many structural isomers does C7H16 have? Draw them.

Answer: 9 structural isomers

2. Identify which of the following are structural isomers for molecule (a).
 Answer:

3. Determine if the structures below are isomers:

a.

b.

c.

Answers: a) No b) Yes c) Yes

4. Which of the following is ​not​ a type of structural isomerism?

E. Functional
F. Positional
G. Chain
H. Optical

Answer: Optical

Conformational Isomerism:

1. Draw the 2 chair conformers of CIS-1,3-dibromocyclohexane and determine which of the 2

conformers is the most stable.

Answer:

The second conformer is anti-staggered and the most stable because the Br substituents are in
the equatorial position.
2. Draw the Conformational Analysis of Propane and identify which is more stable.

Answer: The staggered conformation is more stable than the eclipsed conformation.

3. Draw the most stable conformation of trans-1-tert-butyl-3-ethylcyclohexane.

Answer:
4. Choose the correct potential-energy diagram for rotation about the C-2−C-3 bond of pentane
through 360∘, starting with the least stable conformer.

Answer: 3rd diagram

 Name_______________________________

Even More Resonance Practice Problems

Draw all of the reasonable resonance structures for each of the following molecules.

a. f. k. p.
O O
C N
NH2
H2N
H2N

b. g. l. q.
O O
N C N NH2

c. h. m. r.
O O
C N H2N NH2

H2N

d. i. n. s.
O C N O O

H2N
N

e. j. o. t.
O HN C N O O

OH
HN
Answers to Even More Resonance Practice Problems

a.

O O
O

H2N H2N
H2N

b.

O O
O

c.

O O
O

O
d.
O O
O

N N
N

O O

N N

e.

HN

O O
O

HN HN
HN

f.

C N C N

H2N H2N

g.

N C N N C N
N C N

N C N
h.

C N C N
C N

H2N H2N
H2N

C N

H2N

i.

C N C N C N

H2N H2N H2N

C N C N

H2N H2N

j.

HN C N HN C N HN C N

HN C N
k.

O O

l.

O O O

m.

O O O

n.

O O O
O O O
o.

O O O O
O O

O O

p.

NH2 NH2
NH2

q.

NH2 NH2

NH2 NH2

r.

H2N NH2 H2N NH2 H2N NH2

H2N NH2
s.

t.

OH OH OH

OH