ORGANIC CHEMISTRY 1

MIDTERM: MODULE 1

A Review of General Chemistry

The dawn of Organic Chemistry

1. During the 1800s
* Organic comes from living things (plants and animals)
* Inorganic comes from non-living things (air, minerals, and soil)
* “Only living things can make organic compounds”

2. 1928 (according to Friedrich Wöhler, Father of Organic Chemistry)

* An organic compound CAN be synthesized from an inorganic compound

3. Late 1900s to present

* Organic compounds = contain the element carbon (with a few exceptions)
* Exceptions: Carbonates, CO2, CO

SUMMARY

CHARACTERISTICS OF INORGANIC AND ORGANIC COMPOUNDS

Organic Compound
1. Organic compounds are composed of Carbon, hydrogen, and Oxygen primarily
* Organic compounds contains CHNOPS (Carbon, Hydrogen, Nitrogen, Oxygen,
Phosphorus, Sulfur, all of which are non metals)
2. The nature of organic compounds is covalent due to C-H bonding
3. Melting and boiling points of organic compounds are low
4. Their solubility in water is low
5. They are bad conductors of heat and electricity
6. Some organic compounds are volatile in nature
7. They have catenation property due to C
8. Most of these compounds are colorless
9. Their rate of reactions is generally slow
10. THese compounds are mostly found in living things
11. Examples of organic compounds are; enzymes, protein, DNA, RNA, and fuels etc.
(The four biomolecules are Carbohydrates, lipids, protein, and nucleic acid)
12. Most organic compounds are biodegradable
* Bioassimilation (transport through the cell membrane)
* Produces CO2, H2O
Inorganic Compound
1. Inorganic Compounds are composed of atoms usually other than carbon
* Inorganic compounds mostly contain metals and metalloids
2. The nature of inorganic compounds can be electrovalent, ionic, or covalent
3. Melting and boiling points of inorganic compounds are higher
4. Their solubility in water is high
5. Inorganic compounds are usually good conductors
6. There are almost no inorganic volatile compounds
7. Only some inorganic compounds have catenation properties
8. Inorganic compounds generally have colors
9. Their rate of reaction is fast
10. These compounds are mostly found in non-living things
11. Examples of inorganic compounds are metals, non-metals, salts, etc.
12. Inorganic compounds are generally environment-unfriendly

REVIEW
* Content
* Valence Electrons Lewis
* Lewis Dot Structures
* Ionic vs Covalent Bond
* Electronegativity
* Dipole Moment

Valence Electrons

1. Core Electrons occupy lower energy quantum levels than valence electrons. Inner
electrons.
2. The valence electrons of an element determine its chemical properties. Important
in chemical bonding.

Lewis Dot Symbols of Atoms

* A Lewis dot symbol consists of the symbol of an element and one dot for each
valence electron in an atom of the element.
Writing Lewis Structure of Molecules
Step 1: Count total number of valence electrons to account for.
Step 2: Write the skeletal structure.
Step 3: Draw a single bond between the central atom and each of the surrounding
atoms.
Step 4: Complete the octets of the atoms bonded to the central atom.
Step 5: If the central atom has fewer than eight electrons,
* a) use unaccounted electrons as lone pairs.
* b) take lone pairs from the surrounding atoms to complete the octet of the
central atom and make them double or triple bonds.

Exceptions to Octet Rule

1. Incomplete Octet
* In some compounds, the number of electrons surrounding the central atom in a
stable molecule is fewer than eight.
* Observed for Groups IIA, and IIIA.
2. Odd-Electron Molecules
* Some molecules contain an odd number of electrons.
* Odd-electron molecules are sometimes called radicals.
* Many radicals are highly reactive.
3. Expanded Octet
* Elements in and beyond the third period of the periodic table form some compounds
in which more than eight electrons surround the central atom.

Constitutional Isomers
* Compounds that have the same molecular formula (C2H6O), yet they differ in the
way the atoms are connected
* Different properties
* Different names

Formal Charge in Lewis Structure

* An atom’s formal charge is the electrical charge difference between the valence
electrons in an isolated atom and the number of electrons assigned to that atom in
a Lewis structure.
* FORMULA

* The sum of the formal charges = total charge of the species.

* In a polyatomic ion, the sum of the formal charges is equal to the overall
charge.
* When there are more than one acceptable Lewis structure for a given species, can
often select the most plausible Lewis structure by using formal charges and the
following guidelines:
1. A Lewis structure with no formal charges is preferable.
2. Lewis structures smaller formal charges are plausible.
3. Negative formal charges in electronegative atoms are preferable.

Ionic Bond
* is the electrostatic force that holds ions together in an ionic compound.
* Formed by a transfer of electrons from one atom to another.
Covalent Bond
* A bond in which two electrons are shared by two atoms.
* Octet rule – an atom other than hydrogen tends to form bonds until it is
surrounded by eight valence electrons

* Atoms can share more than two electrons to form multiple bonds.

Covalent Bond: Bond Length, Bond Dissociation Energy

Bond Length
* Bond length is defined as the distance between the nuclei of two covalently
bonded atoms in a molecule.
* Factors: Size of atoms, bond type, electronegativity of the atoms.

Bond dissociation energy, D, (or bond enthalpy)

* It is the quantity of energy required to break one mole of covalent bonds in a
gaseous species.

Bond energy, bond length, and bond order are interrelated properties in this sense:
* the higher the bond order, the shorter the bond length and the greater the bond
energy.
Electronegativity
* Electronegativity, the ability of an atom to attract toward itself the electrons
in a chemical bond.

The bond in HF is called a polar covalent bond, or simply a polar bond, because the
electrons spend more time in the vicinity of one atom than the other.

So is it Covalent or Ionic?
* It is not actually black and white!
* The HF bond and other polar bonds can be thought of as being intermediate between
a (nonpolar) covalent bond, in which the sharing of electrons is exactly equal, and
an ionic bond, in which the transfer of the electron(s) is nearly complete.

* We set a rule-of-thumb nonetheless… Using the difference in electronegativity, Δ

χ

Dipole Moment
* The quantitative measure of the polarity of a bond. Dipole moment (μ), is the
product of the point charge, the electronic charge, and the distance r between the
charges.

* The direction is towards the MORE ELECTRONEGATIVE atom.

* Diatomic molecules containing atoms of different elements (for example, HCl, CO,
and NO) have dipole moments and are called polar molecules.
* Diatomic molecules containing atoms of the same element (for example, H2 , O2 ,
and F2 ) are examples of nonpolar molecules because they do not have dipole
moments.

We do not show the dipole moment for C-H bonds, because though strictly polar, the
electronegativity difference is small.
MESSY PART NG MODULE (MGA EXAMPLES AND ACTIVITY NA MAY SAGOT, AND ANY OTHER ELSE)

EXAMPLES
ORGANIC VS INORGANIC
1.
2.

3.

4.

5.

6.

7.

8.

9.

10.

11.

12.

Incomplete Octet

Odd-electron molecules

Expanded Octet

Constitutional Isomers
1. C3H8O
Formal Charge in Lewis Structure

ACTIVITY (SAGUTAN NIYO)

LEWIS DOT SYMBOL
1. How many "dots" should be shown in the Lewis symbol for phosphorus? A. 1
B. 3
C. 5 D.8

2. Choose the INCORRECT statement.

1. A Lewis symbol consists of a chemical symbol and the outer shell electrons.
2. In a Lewis symbol, the chemical symbol represents the nucleus of the atom.
3. A Lewis structure is a combination of Lewis symbols that represent the transfer
or sharing of electrons in a chemical bond.
4. An ion written as a Lewis symbol has brackets outside the electrons.

Writing Lewis Structure of Molecules

1.1
1. Write the Lewis structure for phosphorous trichloride PCl3.
2. Write the Lewis structure for ozone, O3.
3. Write the Lewis structure for carbon dioxide, CO2 .
4. Draw the Lewis Structure for CH20

Incomplete Octet
1. Which of the following has a molecular structure best described as involving an
"incomplete octet"?
A. OF2 B. BF3
C. CF4 D. NF3
Expanded Octet
1. An expanded octet may occur:
A. in the 1st and 2nd period only B. in families IA, IIA, and IIIA only C.
anywhere except period 1 and 2 D. in the 3rd and 4th period only

Constitutional Isomers

Formal Charge in Lewis Structure

Ionic Bond

Covalent Bond
1. Which of the following is least likely to form multiple bonds?
A. oxygen B. nitrogen
C. carbon D. barium

Bond Length
2. In which of the following molecules would you expect the nitrogen-to-nitrogen
bond to be the shortest?
A. N2H4 B. N2
C. N2O4 D. N2O

Electronegativity
1. Electronegativity is a measure of
1. the energy required to remove an electron from an atom
2. the magnitude of the charge of an electron
3. the energy released when an electron is added to an atom
4. the ability of an atom to draw electron density towards itself

2. Arrange the following in order of increasing electronegativity: Cs, F, As, Cl.

1. As < Cl < Cs < F
2. Cl < As < F < Cs
3. As < F < Cs < Cl
4. Cs < As < Cl < F

3. Choose the INCORRECT statement.

1. Bonds between like atoms are nonpolar bonds.
2. Polar bonds are caused by the bonding pair of electrons being attracted more to
one atom than the other.
3. A difference in electronegativity between two atoms causes a polar bond.
4. If the ΔEN value is large the bond is polar covalent.

4. Classify the following bonds as ionic, polar covalent, or covalent:

1. the bond in C=O bond in acetone,
2. C-Li bond in CH3Li
3. the C—C bond in H3C—CH3 .
4. The C-H bond in CH4

5. Which chloride should have the greatest covalent character?

A. NaCl B. BeCl2
C. KCl D. BaCl2

6. Which of the following exhibits ionic bonding?

A. C2H6 B. Na2S
C. H2CO D. SF4

Which of the following bonds is probably the most polar?

A. N—H in NH3 B. O — H in H2O
C. Se — H in SeH2 D. C — H in CH4
Dipole Moment
ORGANIC CHEMISTRY 1
MIDTERM: MODULE 2

Molecular Geometry and Molecular Dipole

Content
* VSEPR Theory
* Molecular Dipole

MOLECULAR GEOMETRY
* Lewis dot structure only accounts for electron distribution, and not the
structure.
* Molecules are 3 dimensional

* Molecular geometry is the three-dimensional arrangement of atoms in a molecule.

* Molecular geometry can be predicted by the Valence-shell electron-pair repulsion
(VSEPR) model.
VSEPR THEORY
All other molecular structures are derived from the The 5 Parent Geometries

VSEPR Theory
For molecules in which the Central Atom Has one or more lone pairs,
* The geometries are based on the parent geometries.
* We have to take into account the relative repulsive effect of the electron pairs.
The presence of these generally decrease bond angles
For molecules in which the Central Atom Has one or more lone pairs,
Step 1: Draw the Lewis structure.
Step 2: Count the number of electron pairs around the central atom. Multiple bonds
are treated as single bonds. “Bonds + lone pairs” determines the parent structure.

Step 3: Reduce the parent structure by “deleting lone pairs”.

* Reduce trigonal bipyramidal by deleting equatorial arms.
* Reduce octahedral by deleting axial arms
Molecular Dipole
* For a molecule made up of three or more atoms both the polarity of the
bonds and the molecular geometry determine whether there is a dipole moment.
* Even if polar bonds are present, the molecule will not necessarily have a
dipole moment.
Molecular Dipole
* The geometry has to be considered.
* The resultant dipole moment in NH3 is larger than that in NF3 , even if
N—F bonds are very polar.
Review Activity

QNA SA VSEPR THEORY BE

1. Which of the following statements correctly describe the basic concepts

and uses of VSEPR theory:
I) The VSEPR theory is used for estimating bond angles.
II) The VSEPR theory is used for predicting electronegativities.
III) The VSEPR theory is helpful in predicting polarity.
IV) The VSEPR theory states that electron pairs repel each other.
V) The VSEPR theory uses valence electron counting for structure prediction.

A) I), II), III), IV)

B) I), II), IV), V)
C) II), III), IV), V)
D) I), III), IV), V)

2. The electron-pair geometry of H2O is ________.

A) tetrahedral
B) linear
C) trigonal planar
D) bent

3. What are the ideal bond angles for H2O?

A) 120°
B) 109.5°
C) 90°
D) 75°

4. Which of the following is a bent (nonlinear) molecule?

A) CO2
B) BeF2
C) OF2
D) XeF2

5. Which of the following molecules has both an electron group geometry

and a molecular geometry described as trigonal planar?
A) PF3
B) OF2
C) CHF3
D) BF3

6. Which of the following species has a pyramidal structure?

A) ClO3 -
B) ClO4 -
C) ClO2 -
D) ClO2
 7. What is the correct molecular geometry for SeBr3 +?
A) trigonal pyramidal
B) tetrahedral
C) trigonal planar
D) T-shaped

8. For ammonia, determine the (1) parent structure i.e. the arrangement of
the electron pairs around N, and (2) the molecular geometry.
A) tetrahedral, trigonal pyramidal
B) square planar, trigonal planar
C) octahedral, square base pyramidal
D) trigonal bipyramidal, T-shaped

9. Which of the following is the BEST description of the geometry of PCl3?

A) trigonal pyramid
B) square pyramid
C) octahedral
D) trigonal bipyramid

10. Which species has a trigonal planar geometry?

A) CIF3
B. NCl3
C) CO32-
D) I3-

11. One of the following ions has a trigonal-planar shape: SO32- ; PO43- ;
PF6- ; CO32-. Which ion is it? Explain.

12. Consider the molecules SCI2, SO3, SOCI2. What are the shapes of these
molecules, in the order given?
A) linear, trigonal pyramidal, trigonal planar
B) linear, trigonal planar, trigonal pyramidal
C) angular, trigonal planar, trigonal pyramidal
D) angular, trigonal planar linear

13. Use the VSEPR theory to predict the shapes of the anions (a) ClO4-;
(b) S2O32- (that is, SSO32-); (c) PF6-; (d) I3-

14. The molecular geometry of XeF4O is

A) trigonal
B) octahedral
C) trigonal bipyramidal
D) square pyramidal
E) tetrahedral

15. The central atom of a molecule, AX4, is surrounded by four single

bonds and a lone pair. Determine the geome- try of the molecule.
A) tetrahedral
B) square base pyramidal
C) square planar
D) see-saw

16. Determine the ideal bond angle of AlCl3.

A) less than 60°
B) 60°
C) 120°
D) 180°

PART 2
1. Choose the INCORRECT statement.
A) The geometrical distribution of electron groups is the electrongroup geometry.
B) A polar molecule has a dipole moment.
C) A dipole moment is the product of the number of atoms and the charge.
D) A nonpolar molecule can have polar bonds.

2. Which of the following molecules is nonpolar?

A) HCN
B) CHCl3
C) HClO4
D) BCl3

3. Predict whether each of the following molecules has a dipole moment:

(a) BrCl, (b) BF3 (trigonal planar), (c) CH₂Cl₂ (tetrahedral).

4. Which of the following have a zero net dipole moment?

(1) CO₂ (IV) O3
(II) H₂O (V) CHCl3
(III) CH4 (VI) NH4+

A) II and VI
B) I, III and VI
C) I, IV, and VI
D) IV and V
 5. Three monosulfur fluorides are known:
I. SF2
II. SF4
III. SF6

Of these, polar species include _________.

A. I and II only
B. II only
C. II and III only
D. I only
6. For which of the following may we draw both polar and non-polar Lewis
structure?
A) NH3
B) SF2Cl4
C) PCl5
D) BF3

QNA SA MOLECULAR DIPOLE BE

(imaginin nyo nalang wala yung ans key)
SAGUTAN NIYO PO
Which is more polar, :NH3 or :NF3?

ORGANIC CHEMISTRY 1
MIDTERM: MODULE 3
Valence Bond (VB) Theory

s orbitals
* Spherical shape
* Parity: gerade, g.
* Symmetric with respect to inversion
* Also known as simple.

p orbitals
* Dumbbell shaped
* Parity: ungerade, u.
* Unsymmetric with respect to inversion.
* Also known as principal
d orbitals
* Four-leaf clovers
* Parity: gerade, g.
* Symmetric with respect to inversion.
* Also known as diffuse

f orbitals
* Also known as fundamental
Valence Bond (VB) Theory

1. The covalent H—H bond is formed by the overlap of the two 1s

orbitals in the H atoms. The two orbitals share a common region in space.
2. Electrons are paired wherever possible.
3. A stable molecule forms when the potential energy of the system
has decreased to a minimum.

Repulsion (p-p and e-e) = Attraction (p-e)

For Homonuclear Diatomic Molecules:

For Heteronuclear diatomic molecules:
VB: Hybridization of Atomic Orbitals
Accounting for geometry in more complex molecules

Consider CH4
For the C to form geometrically correct bonds with the 4 H, we need:
1) 4 unpaired electrons in C, each for one H atom
2) A tetrahedral geometry

Accounting for geometry in VB

Consider CH4
The 2s, 2px , 2py , and 2pz orbitals of C will hybridize to form 4 sp 3 hybrid
orbitals that have the desired correct geometry.
All possible hybridization scheme
* Each set of hybrid orbitals is associated with a particular shape,
although this may not coincide with the molecular shape if lone pairs also have to
be accommodated:

* sp linear
* sp² trigonal planar
* sp³ tetrahedral
* sp³d (dz2) trigonal bipyramidal
* sp³d (dx2 - y2) square-based pyramidal
* sp³d² octahedral
* sp2d square planar
VB: Hybridization of Atomic Orbitals
How about multiple bonds?
sigma bonds (σ bonds)
* covalent bonds formed by orbitals overlapping end-to-end, with the
electron density concentrated between the nuclei of the bonding atoms.

pi bond (π bond)
* which is defined as a covalent bond formed by sideways overlapping
orbitals with electron density concentrated above and below the plane of the nuclei
of the bonding atom
The C—C sigma bond cannot twist because of the pi bond. Thus, the molecule stays
planar.
QNA BE SAGUTION NYO

1. The description of covalent bond formation as a region of high

electronic charge density resulting from overlap of atomic orbitals between the two
bonded atoms is referred to as:
A) atomic orbital theory
B) MO Theory
C) hybridization theory
D) valence-bond Theory

2. Find the correct statements about the bonding in methane, CH4.

I. The carbon s and p orbitals combine to form four equivalent sp3 orbitals
II. All C-H bonds have the same strength
III. Molecular geometry is different from electron group geometry
IV. Four C sp3 orbitals combine with the s orbitals of the hydrogens to form bonds

A. I, II, III
B. I, II, IV
C. I, III, IV
D. I, III IV

3. The three molecular shapes an sp3 hybridized molecule can have

are ________.
A) triangular, bent, T-shaped
B) irregular tetrahedron, T-shaped, linear
C) octahedron, square pyramid, square planar
D) tetrahedron, trigonal pyramid, bent

4. If the wave functions describing the 2s and two of the 2p

orbitals are combined, the identical orbitals derived form bond angles of _____.
A) 90°
B) 120°
C) 180°
D) 109.5°

5. The SF5 ion has a square pyramid structure. The hybridization of

the orbitals in sulfur is
A) sp³d
B) sp³d²
C) sp³
D) sp²

6. Which combination of hybrid orbital descriptions and electronic

geometry descriptions is INCORRECT?
A) sp/linear
B) sp2 /trigonal planar
C) sp3d/square planar
D) sp3d2 /octahedral

7. According to the principles of VSEPR applied on ICl5 , which of

the following is INCORRECT?
A) VSEPR formula = AX5E
B) molecular geometry = square pyramid
C) hybridization = sp3d
D) electron pair geometry = octahedral

8. Which statement is INCORRECT?

A) The bond length is the internuclear distance.
B) Hybrid orbitals are combinations of atomic orbitals.
C) There are the same number of hybrid orbitals produced as the number of atomic
orbitals combined.
D) An sp hybridization produces a tetrahedral molecule

9. According to VB theory, which hybrid orbitals overlap to form the

O-H single bonds in H₂O?
A) s of H and sp² of O
B) s of H and sp³ of O
C) sp³ of H and sp³ of O
D) s of H and s of O

10. The double covalent bond between two carbon atoms in ethylene
(C2H4):
A) is free to rotate because of delocalized electrons
B) consists of one sigma and one pi bond
C) has a low electron density
D) includes a "lone pair" of electrons on one of the carbons

11. Which statement regarding VB theory is INCORRECT?

A) A single bond is a sigma bond.
B) A triple bond is two sigma bonds and a pi bond.
C) A double bond requires each atom to have an unhybridized p orbital.
D) Both atoms in a triple bond have linear geometry.

12. Which statement regarding VB theory is INCORRECT?

A) d orbitals are not included in hybrid orbitals.
B) Hybrid orbitals use atomic orbitals from the outermost shell.
C) Sigma bonds are end-to-end overlaps.
D) Pi bonds are overlaps of parallel p orbitals.

13. Choose the INCORRECT statement about HCN.

A) There are two π bonds.
B) N has a lone pair.
C) The molecule is bent.
D) C has sp hybridization.

14. .
 15. Which of the following statements concerning the carbon dioxide
molecule is correct?
A) The molecule contains two lone pairs of valence electrons.
B) The molecule contains two σ bonds.
C) The molecule contains four π bonds.
D) The carbon is described by sp2 hybridization.

16. .

17. .
 18. Which compound includes a carbon atom with an sp hybridized
orbital?
A) Benzene
B) Methyl Chloride
C) Phenol
D) Butyne

19. What are the hybridizations of carbon 1 and carbon 2 in the

hydrocarbon shown below? (Note: bonds are not shown)

A) sp3, sp
B) sp3, sp2
C) sp2, sp2
D) sp, sp2

20. The hybrid orbitals used by carbon in benzene are:

A) sp³
B) dsp³
C) sp
D) sp²

21. Which of the following has a bond formed by the overlap of an

sp² hybrid orbital with an sp hybrid orbital?
A. CH2=CHCH3
B. CH2-CH2
C. CH2=C=CH2
D. CH3C=CCH2CH3

22. In which species are all the carbon atoms considered to be

sp² hybridized?
A. C2H2
B. C2H4
C. C3H8
D. C4H10
 23. What is the hybridization of the carbon in a carboxyl group?
A. sp
B. sp³
C. sp²
D. dsp³

24. Which statement is correct for the structure shown?

A) Carbon no. 1 is described by sp3 hybridization.

B) Carbon no. 2 is described by sp2 hybridization.
C) The molecule contains a total of five π bonds.
D) Carbon no. 7 is described by sp hybridization

25. What is the hybridization state of the central N atom in

the azide ion, N3 -?

26. What is the hybridization state of the hydroxyl oxygen in

an alcohol?

27. What is the hybridization state of the acyl oxygen in a

ketone?

28. Determine the hybridization state of ever atom here:

 29. How many sigma bonds and pi bonds are there in each of
the following molecules?
ORGANIC CHEMISTRY 1
MIDTERM: MODULE 4

LIQUID AND IMFAs

Bulk Phases of Matter

Phase Transition
Why do molecules behave differently among the three phases?

* What primarily distinguishes between the states of matter

is the Strength of IMFAs Intermolecular Forces of Attraction

Intramolecular Forces

1. Covalent interactions
* Hold atoms together in a molecule
* Forces between atoms in the same molecule
* Stabilize individual molecules.

Intermolecular and Inter-ionic Forces (IMFAs)

1. Non-covalent interactions
* Attractive forces between molecules and ions.
* Primarily responsible for the bulk properties of matter
(for example, melting point and boiling point).

Intermolecular Forces and Phase Transition

* If IMFs are strong, it is hard to separate molecules from
each other.
* More energy (higher temperature) is needed to pull them
apart. Therefore;
* Higher boiling point
* Higher freezing (melting) point
Three types of vdW forces
* Dipole-Dipole
* Dipole-Induced Dipole
* London Dispersion Forces

Forces involving ions

* Ion-induced dipole
* Ion-dipole
* Ion-ion

van der Waals forces

* the collection of intermolecular forces that are a
consequence of dipole moment and polarizability.
* Dipole moment and polarizability describes the
distribution of electron density within a molecule
* Three types of vdW forces
* Dipole-Dipole
* Dipole-Induced Dipole
* London Dispersion Forces

Dipole moment
* consequence of molecular geometry and electronegativity
differences.
Polarizability
* “fluffiness” of the electron cloud.

dipole moment, μ
* exists in a molecule where bond dipoles do not totally
cancel out each other.
* For a molecule, it is the summation of the bond dipoles.
* If there is a net dipole, then the molecule is polar.
* Dipole moment is permanent.

Polarizability, a,
* Polarizability, a, of a molecule provides a measure
of the extent to which its electron cloud can be distorted from its “normal” or
“average” shape,
* Depends on how diffuse or “spread out” its electron
cloud is.
* Expressed in units of volume.
* Related to the volume of its charge cloud.
* Gives a molecule a temporary dipole moment.
A polarizable molecule becomes polar when:
1. an externally applied electric field is applied.
2. By the approach of another molecule or ion.
 1. dipole-dipole interaction
* The observed boiling point of CHF3 is more than 40 °C
higher than that of CF4.

* Interaction between a pair of polar molecules.

* A polar molecule has a permanent dipole moment.
* Polar molecules tend to line up with the positive end
of one dipole directed toward the negative ends of neighboring dipoles.

2. dipole - induced dipole interaction

* All molecules (polar or nonpolar) are polarizable.
* The electronic charge cloud of a molecule will always
be distorted to some extent by the approach of a polar molecule

3. London Dispersion Forces

* Explaining IMFs in non-polar molecules
* Because the electrons in a molecule are in constant
motion, at some particular instant, electrons are concentrated in one region of a
molecule.
* This displacement of electrons causes a normally
nonpolar species to become momentarily polar. An instantaneous dipole is formed.
The molecule gains an instantaneous dipole moment.
* After this, electrons in a neighboring molecule may be
displaced to produce a dipole — an induced dipole.
* We can call this interaction an instantaneous dipole –
induced dipole attraction, but the names more commonly used are dispersion force
and London force.

* Keep in mind! Dispersion forces exist among species of

ALL types, whether they are neutral or bear a net charge and whether they are polar
or nonpolar.
* Dispersion forces become stronger as polarizability
increases. Polarizability increases with molecular mass, because of larger number
of electrons.
3. London Dispersion Forces
* Can also be interatomic.

Forces of Attraction involving ions

1. ion – dipole interaction
* The strength of this interaction depends on the
(1) charge density of the ion and on the
(2) magnitude of the dipole moment and size of the molecule
* Cation interacts more strongly with dipoles than does
an anion having a charge of the same magnitude. Why?
* Reason why ions dissolve in water.

* The higher the ion’s electron density, the stronger

2. Ion-induced dipole interaction

* 3-15 kJ/mol

* The stronger the charge is, the more polarizing it.

* The bigger the species the more polarizable it is.

3. Ion-ion interaction (Ionic)

* 400-4000 kJ/mol
 * Increasing strength of IMFA
* Ion-ion > Ion dipole > H-Bonding > dipole-dipole >
ion-induced dipole > dipole-induced dipole > LDF

A special dipole-dipole: H-Bond

Hydrogen bond
* Special type of dipole-dipole interaction between
the hydrogen atom in a polar bond N–H, O–H, or F–H, and a lone pair in a
electronegative O, N or F atom
* 10-40kJ/mol

* H-Bond donor = electronegative atom

* H-Bond acceptor = Lone pair in a electronegative
atom

Hydrogen bond in pure water

* Density decreases as water is heated

* Low density at 0° because of H-bonding structure
* Liquid water reaches maximum density at 3.98° C

* 0°C Ice – 4 HB per molecule, crystal structure,

hexagonal arrangement, rather open, making it less dense

* As ice melts, some HBs are broken, some molecules

gets trapped in the lattice, more compact arrangement, more dense*
* The trapping of free water molecules in cavities
and thermal expansion—act in opposite directions.

* When the temperature reaches 0 – 4 °C, H bonds are

broken, crystal is slowly falling apart. Trapping prevails. increase in density
* 4 °C – last crystal structure falls apart, maximum
density achieved (3.98°C).
* 4 – 100, decrease in density. Thermal expansion
predominates.

Figure 11.13
* Plot of density vs. temperature for liquid water
* The maximum density of water is reached at 4°C
* The density of ice at 0°C is about 0.92g/cm3

Hydrogen bond
* In acetic acid, CH3COOH, pairs of molecules tend to
join together into dimers, both in the liquid and in the vapor states.
* As a result, the heat of vaporization is abnormally
low than what is expected from such structure.
* Dimerization

* You would expect it to have a really high boiling

point. But no. There is not much IMFAs left among the dimers themselves.
* Dahil nga nagamit na nila nung nag bond sila sa
sarili nila (dimer)
 * Effect to physical properties

Intramolecular H-Bonds - within the molecules

* ortho structure
* Has intramolecular HB
* Less available for Intermolecular HB
* m.p. = 158.6 °C.

* para structure
* NO intramolecular HB
* ALL available for Intermolecular HB
* m.p. = 214.5 °C.
* Ortho and para is same molecule pero iba ng
pagkaposition, iba rin m.p dahil yung ortho is nagamit na yung HB niya within
itself (INTRA) si para naman is malayo, so nde niya pa nagamit, available siya sa
INTER HB

Liquids : Strong IMF

* High: b.p., m.p, surface tension, viscosity
* Low: vapor pressure, volatility

REVIEW ACTIVITY
Review Activity
1. Which of the following statements concerning
molecules in the liquid state is true?
A. The molecules contract to fit the size of the container.
B. The molecules have no motion.
C. The molecules are in a patterned (oriented) arrangement.
D. The molecules are mobile and relatively close together
 2. A passage of substance directly from the vapor to
the solid state is known as:
A. deposition
B. Sublimation
C. solidification
D. fusion

3. Which of these molecules would you expect to be

polar?
Cl2 , ICl, BF3 , NO, SO2

4. A polar solute usually dissolves in a polar

solvent and a nonpolar solute usually dissolves in a nonpolar. This is
A. Hund’s Rule
B. Henry’s Law
C. the solubility rule
D. the “like dissolves like” rule

5. The following molecules are of similar sizes.

Arrange in terms of increasing b.p
A. CO
B. NO
C. O2

6. Explain why a solution of Bromine water is

possible

7. Which probably has the lowest boiling point at 1.0

atm pressure?
A. PbH4
B. SnH4
C. SiH4
D. GeH4
E. CH4

8. Which probably has the lowest boiling point at 1.0

atm pressure?
A. C2H6
B. C6H14
C. C3H8
D. C5H12
 9. Which compound would you expect to have the
highest melting point?
A. isobutyl alcohol
B. sec-butyl alcohol
C. butyl alcohol
D. tert-butyl alcohol

10. Which will have the highest boiling point?

11. Which would have higher b.p.?

1. 1. Ar or Ne
2. I2 or Br2
3. Propane or octane
4. n-pentane or neo-pentane

12. Which of the following hydrocarbons has the

lowest boiling point?
A. C4H10
B. CH4
C. C6H6
D. C2H6

13. If one compares compound A, composed of nonpolar

molecules, with compound B, composed of polar molecules, and both molecules have
the same molecular formula, then it is true that:
A. both compounds have the same boiling point
B. A boils at a lower temperature than B
C. B boils at a lower temperature than A
D. we have to know the structural formula to determine the differences in boiling
points of A and B

14. Which ion has stronger ion-dipole interaction

with a polar molecule?
A. Al3+
B. Na+
C.K +
D. O2-
E. S2-

15.
PART 2
1. Which molecule has stronger ion-dipole interaction
with Na+?
1. HF
2. NH3
3. NF3
2. What type(s) of intermolecular forces exist
between the following pairs:
1. HBr and H2S,
2. Cl2 and CBr4
3. What type(s) of intermolecular forces exist
between the following pairs:
1. I2 and NO3-
2. NH3 and C6H6
4. Below are given the Lewis structures of four
molecules. Which one displays the LEAST hydrogen bonding?
1. 2.
3. 4.

5. The following compounds have very similar molar

masses. What would be the correct order when they are arranged in order of
INCREASING strength of their intermolecular forces?
I. C3H8
II. CH3OCH3
III. CH3CH2OH
5. II<I<III
6. III<I<II
7. I<II<III
8. III<II<I
6. Which of the following can form hydrogen bonds
with water?
1. CH3OCH3
2. CH4
3. F-
4. HCOOH
 5. Acetone
6. CH3OH
7. Ammonia
8. hydrofluoric acid
7. Which compound is expected to be most soluble
in water at 25°C?
1. N2
2. O2
3. (CH2H5)2NH
4. C2H5OC2H5
8. Which of the following can form hydrogen bonds
with itself?
1. CH3OCH3
2. CH4
3. F-
4. HCOOH
5. Acetone
6. CH3OH
7. Ammonia
8. hydrofluoric acid
9. Which of the following species are capable of
hydrogen bonding among themselves?
1. H2S
2. C6H6
3. CH3OH
10. Which probably has the highest boiling point
at 1.00 atmpressure?
1. H2NCH2CH2NH2
2. CH3CH2CH2NH2
3. CH3CH2NHCH3
4. (CH3)3N
11. Which compound is least soluble in water?
1. CH3CH2CH2F
2. CH3CH2CH2NH2
3. CH3CH2CH2OH
4. CH3CH2CH2COOH
12. The following compounds have identical
molecular weights. Which would have the lowest boiling point?
1. 2methyl-1-propanol
2. 2-butanol
3. 1,1-dimethylethanol
4. 1-methoxypropane
13. Determine the type of non-covalent interaction
depicted:
1. 2.
3. 4. 5.
14. Water is generally a good solvent for polar molecules and a poor solvent for
non-polar molecules. The solvent properties are best explained by which of the
following
1. High surface tension
2. The ability to form intermolecular hydrogen
bonds
3. The high density of liquid water relative to
polar solvents
4. The high heat of vaporization
15. Which would you expect to have the higher
boiling point, the hydrocarbon fuel butane, C4H10, or the organic solvent acetone,
(CH3)2CO?
1. 16.
Which compound has the highest boiling point
1. CH3CH2CH3
2. CH3(C=O)CH3
3. CH3OCH2CH3
4. CH3CH2CH2OH
17. Arrange the liquids represented by the
following molecular models in the expected order of increasing normal boiling point
1.
18. Arrange the following in the expected order of increasing boiling point:
1. octane, Butane, Isobutane, and
Benzaldehyde.
19. Arrange the following substances in
the order in which you would expect their boiling points to increase:
1. CCl4 , Cl2 , ClNO, N2
20. Arrange the following in order of
increasing boiling point:
1. Ne, He, Cl2, acetone, O2, O3
21.
22. What makes water a liquid at room temperature
1. Non-covalent interactions
2. Van der waals forces of attraction
3. Covalent bonding
4. Hydrogen bonds between water
molecules
ORGANIC CHEMISTRY 1
MIDTERM: MODULE 5

ACIDS AND BASES

Contents
* Brønsted–Lowry Theory
* Factors that affect strength of
acids and bases
* Levelling & Solvating Effect
* Lewis Acids and Bases

Brønsted–Lowry Theory of Acids and Base

* When you put acetic acid in water,
what exactly happens?

* When added to water, acids protonate

water molecules to form hydronium (H3O+) ion. Water here acts as a base.

Flow of Electron Density: Curved- Arrow Notation

* There is a flow of electron density
that causes a proton to be transferred from one reagent to another; the curved
arrows illustrate this flow.
* The arrows show the reaction
mechanism; that is, they show how the reaction occurs in terms of the motion of
electrons.

Strong ARRHENIUS ACIDS AND ARRHENIUS BASES

* Strong acids have a strong tendency
for producing H+ ions. These essentially fully dissociate in aqueous solutions.

* Strong bases have a strong tendency

for producing OH- ions. These essentially fully dissociate in aqueous solutions

Note: Ca(OH)2 is only slightly soluble, while Mg(OH)2 is only very sparingly
soluble. However, the small amount that dissolves is fully ionized.
Strong bases
* NOTE THE FOLLOWING ORGANIC STRONG
BASES:

Weak ARRHENIUS ACIDS AND ARRHENIUS BASES

* Weak acids are molecular
compounds that have a weak tendency for producing ions; weak acids are very
partially ionized in aqueous solution.
* The vast majority of acids are
weak acids. The ionization of a weak acid is

* Weak bases have a weak tendency

for producing OHions.
* These don’t usually have (OH) in
their formula, but react with water to produce the hydroxide, i.e. Nitrogen bases.

Acid Ionization (dissociation) Constants, Ka

* All acids have a particular
identifying Ka at any temperature

Note:
* A stronger acid will produce a
weaker conjugate base.
* A weaker acid will produce a
stronger conjugate base.

* A stronger base will produce a

weaker conjugate acid.
* A weaker base will produce a
stronger conjugate acid.

Base Ionization Constants, Kb

* All bases have a particular
identifying Kb at any particular temperature

Using pKa Values to Predict the Position of Equilibrium

* The equilibrium will always favor
formation of the weaker acid (higher pKa value).

* For some reactions, the pKa

values are so vastly different that for practical purposes the reaction is treated
not as an equilibrium process but rather as one that goes to completion

Brønsted- Lowry Acidity

Conjugate Base Stability
* When comparing acids with no net
charge (HA vs. HB), the MORE ACIDIC compound is the one that can produce the more
stable conjugate base

Brønsted- Lowry Acidity: Factors Affecting the Stability of Anions

* Chlorine is an electronegative
atom, and it can therefore stabilize a negative charge.
* The chloride ion (Cl−) is in fact
very stable, and therefore, HCl is a strong acid.
* HCl can serve as a proton donor
because the conjugate base left behind is stabilized

* When butane is deprotonated, a

negative charge is generated on a carbon atom.
* Carbon is not a very
electronegative element and is generally not capable of stabilizing a negative
charge.
* Since this C− is very unstable,
we can conclude that butane is a very weak acid.

Factors Affecting the Stability of Anionic Conjugate Bases

1. Which atom bears the charge?

Trends in Strength of Acid/Base

Strengths of Binary Acids
* When comparing binary acids of
elements in the same row of the periodic table, acid strength increases as the
polarity of the H—Y bond increases (electronegativity of Y).

* When comparing binary acids of

elements in the same group of the periodic table, acid strength increases as the
bond length of the H—Y bond increases (atomic radius of Y).
 * HF is anomalously weaker than the
other haloacids, because of very strong hydrogen bonding.
* The fluoride strongly forms an
ion pair with the hydronium ion.
* This is because fluorine is
highly electronegative.

* The trend of the strength of the

corresponding conjugate bases is the exact opposite

2. Resonance

3. Induction

* Notice the trend. With each

additional Cl, the compound becomes more acidic.

Strengths of Oxoacids

4. Orbitals

* Acetylene is 19 orders of
magnitude more acidic than ethylene.

Ranking the Factors that Affect the Stability of Anions (ARIO)

NOTE: Only an approximation, does not always work.

Brønsted-Lowry Acidity:
Assessing the Relative Acidity of Cationic Acids
* To assess the acidity of cationic
acids (HA + vs. HB + ), we can compare the stability of the positive charges in the
cationic acids
* Oxygen is more electronegative
than nitrogen, and therefore, oxygen can better stabilize a negative charge, but
the opposite is true for positive charges.
* When it comes to stabilizing a
positive charge, nitrogen can better stabilize the charge, because nitrogen is less
electronegative than oxygen

* Recall that a weaker acid

produces a stronger conjugate base, while a stronger acid produces a weaker
conjugate base.
* This explains why ammonia (NH3 )
is a stronger base than water (H2O):

Strengths of Amines as Bases

* When an atom or group of atoms
more electronegative than H replaces one of the H atoms of NH3 , it becomes a
weaker base than NH3 , because the lone pair cannot bind the proton as strongly.
* Amines act as bases, because the
lone pair acts as a proton acceptor. The more available the lone pair is, the
stronger the base.

* Carbon is less electronegative

than N, and tends to have electron donating effect to N by induction.
* Hydrocarbons improve the basicity
of NH3 .

Note: Benzene ring however is an electron withdrawing group and has the opposite
effect. Aniline is a weaker base than NH3 .
Leveling Effect
* “The base cannot be stronger than
the conjugate base of the solvent.
* If the solvent is water, than
hydroxide is the strongest base that can be used.”
* Example: The amide ion (H2N- )
cannot be used if the solvent is water. It will be converted to ammonia, and
destroy the solvent.

* In order to work with an amide

ion as a base, we use liquid ammonia (NH3 ) as a solvent.
* Hexane and THF, that can be used
to dissolve very strong bases

* The leveling effect is also

observed in acidic solutions.

* In summary, the leveling effect

dictates the strongest base and the strongest acid that can exist in any particular
solvent.
* A base cannot be stronger than
the solvent’s CB.
* An acid cannot be stronger than
the solvent’s CA
Solvating Effects
* In some cases, solvent effects
are invoked to explain small differences in pKa values.

* The tert-butoxide ion is very

bulky, or sterically hindered, so the anionic oxygen atom is less capable of
interacting with the solvent.
* Ethoxide is better solvated and
is therefore more stable than tert-butoxide. This effect is weaker than AIRO.

Lewis Theory of Acids and Bases

* Lewis acids are species with
vacant orbitals that can accommodate electron pairs;
* Lewis bases are species that have
lone-pair electrons available for sharing.

* Definition includes reagents that

would otherwise not be classified as acids or bases.

REVIEW ACTIVITY
QNA BE SAGUTION NYO

1. Which of the following is NOT an

acid-base conjugate pair?
A) NH3 and NH4+
B) H2S and OH-
C) H2O and OH-
D) HCN and CN-

2. Is it appropriate to describe
each of the following as a conjugate acid-base pair? Explain.
a) HCO3- and CO32-
b) HSO3- and SO42-
c) H2CO3 and H2C2O4
d) HClO and ClO-
e) H2S and S2-
3. .

4. .

5. .
6. .

7. .

8. .

9.
10. .

11. .
 12. .

13. Which is a stronger base?

A) NH2- or F-
B) I- or Br-
C) HO- or HS-

14.

15. .

16. .
17. .

18. .

19. .

20. .
 21. .

22. .

For ans key chinecheck nyo nalang sa mismong ppt ne

23. .

24.
25. .

26. .
27. .

28. .

29. .
30. .

31. .

32. .
 33. .

34. Same
question sa #33

35. .
36. .

37. .

38. .

39. Under the Lewis concept of acids and bases, an acid is ______.
A) an electron pair donor
B) a proton acceptor
C) a proton donor
D) an electron pair acceptor

40. Which of the following cannot behave as a lewis base? (hindi lang isa sagot
here)
A) NH3
B) OF2
C) CH4
D) OH-
E) Fe3+

41. .

42. .
43. .

44. AlCl3 is a catalyst used in the alkylation of aromatic compounds. It is a/an

__________.
A) Lewis Acid
B) Bronsted-Lowry Acid
C) Arrhenius Acid
D) Lewis Base

45.