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 CHEMISTRY IN FOCUS PP3.1

PP
Victoria, this PrePacket 3.1 begins to address the fundamentals of ACIDS and
BASES. It is, quite literally, an INTRODUCTION. We’ll get into the “uglier” aspects of
acid-base chemistry in session.

INTRODUCTION: ACIDS and BASES - A Brief Overview

3.1 The acids and bases that you have used so far in the laboratory are probably the
standards you’ll find in most labs: aqueous solutions of relatively simple inorganic
substances, such as hydrochloric acid, sulfuric acid, sodium hydroxide, and the like.
But acids and bases are important in our everyday lives when we are not in the lab
– what I am saying here is that we encounter them on a DAILY BASIS!

First of all, acids and bases are ubiquitous: they are EVERYWHERE you turn,
including in the foods we eat and the beverages we drink. VIC, ARE YOU A
FANATIC OF WINE? Well, if so, you might already know that the characteristic
flavor of the grapes is what distinguishes wines from each other, and this
characteristic flavor is largely due to two very closely related acids called
tartaric acid (H2C4H4O6) and malic acid (H2C4H4O5).

# of Elements: 17
Topics: CHEMISTRY

Time: Will vary: Anywhere from 60-90 minutes

TBCB: NEXT SESSION

Notes/Instructions: CHEMISTRY: Acids and Bases

Check these off as we
complete them.

PrePacket 3.1

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HW1 Tartaric and Malic Acid
All of the following are true in comparing tartaric acid and malic acid except that

A. they are both weak dicarboxylic acids C is correct. Constitutional isomers are
compounds with the same molecular
B. they both have an index of hydrogen deficiency =formula,
2 yet they differ from each other in
the way the atoms are connected—that is,
C. they are constitutional isomers they differ in their constitution.
D. they both contain at least one stereocenter
Tartaric and malic acid are NOT
constitutional isomers.

Tartaric acid and malic acid are organic acids and are, expectedly, found in several biological
systems. Going back to the grapes, fermentation of the sugars in the grapes ultimately forms good
‘ol vinegar, the tangy, sour flavor of which is attributable to another weak acid: acetic acid
(CH3COOH), the second simplest carboxylic acid.

The sour taste of oranges, lemons, and other citrus fruits stems from citric acid (H3C6H5O7), and, to
a lesser extent, ascorbic acid (H2C6H6O6)  this is better known to us as Vitamin C.

HW2 Carboxylic Acid “Acidity”

The acidity of a carboxylic acid is primarily attributable to:
I. Resonance stabilization
II. Delocalization of negative charge between two oxygen atoms
III. Ring stabilization of pi electrons
B is correct. The conjugate bases of carboxylic acids exist as
A. I only hybrids of two resonance forms. Within the resonance forms,
the negative charge is “shared” between two, electronegative O
B. I and II atoms; this “sharing” lowers the potential energy of the
conjugate base, making it more stable. Because of this stability,
C. I and III
the parent acid will, more readily, release a proton to become
D. II and III this STABLE CONJUGATE BASE  this makes the parent acid
more acidic.
Victoria, it is important to have a decent appreciate for acids and bases before we get into the nitty gritty
“chemistry” of how they function and affect us. They are, for sure, among the most important substances in
chemistry, and they affect our daily lives in innumerable ways.
Besides being present in our foods, acids and bases are also crucial components of living systems.
Some key examples:

 amino acids: they are used to synthesize proteins; they are actually “acidic” because of their
carboxyl groups which make them WEAK carboxylic acids.
 nucleic acids: DNA and RNA  code genetic information.
 citric and malic acids: are among several acids involved in the Krebs cycle (also called the citric
acid cycle) that is used to generate energy in aerobic organisms.

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  application of acid–base chemistry: has also had critical roles in shaping modern society,
including such human-driven activities as industrial manufacturing, the creation of advanced
pharmaceuticals, and many aspects of the environment.
I know this is just a brief introduction, but my hope is that the impact of acids and bases is now more
EVIDENT to you. That impact depends not only on the type of acid or base, but also on how much is
present (or alternatively, the amount):

Some considerations on what I mean by “type” and “amount”:

1) the time required for a metal object immersed in water to corrode (will depend on the type of acid
as well as the amount)
2) the ability of an aquatic environment to support fish and plant life
3) the fate of pollutants washed out of the air by rain, and
4) even the rates of reactions that maintain our lives all critically depend on the acidity or basicity of
solutions

Victoria, above I explained ever so briefly why amino acids are considered ACIDIC. It is, of course,
because of the carboxyl group. Check out this question:

HW3 A CARBOXYLIC ACID REACTION

A carboxylic acid is an organic compound with a carboxyl group (COOH) attached to an alkyl or
aryl group. Although weak in acidity, it will react readily with an alkali metal. Consider the
following reaction between two carboxylic acid equivalents and 2 equivalents of sodium metal:

2R-COOH + 2Na ��
� 2R-COO- Na + + ?
The missing product is:
B is correct. The two equivalents of carboxylic acid will
A. one equivalent hydroxide anion (HO ) EACH release a proton to yield the corresponding,
-
negatively charged carboxylate conjugate base. The
B. one equivalent of diatomic hydrogen (Htwo
2) anions will ionically bond to the two sodium
cations to form two equivalents of salt (sodium
C. two equivalents of hydride anion (H-) carboxylate). The two protons then join to form the
D. two equivalents of protons (H+) diatomic hydrogen gas product, H2.

HW4 AN ASIDE
A carboxylic acid contains the full carboxyl group (-COOH). Within this group, we have the active
carbonyl entity: the C atom DOUBLE BONDED to the O atom (C=O). This O atom is electron-
rich and can therefore act as a NUCLEOPHILE (or LEWIS BASE).

Recall that when we are drawing (or following) a mechanism, our arrows serve very specific
purposes – they account for electron movement. Remember that electrons FLOW in ALL
REACTIONS (except nuclear). Also, the electrons originate at a site of HIGHER ELECTRON
DENSITY (e.g. a π bond, a lone pair) and point to an area of LOWER ELECTRON DENSITY (e.g. a
carbocation, a partially positively charged atom). Here are two simple electron flow steps. Which
is CORRECT and which is INCORRECT? Just check the appropriate choice.

___ Correct  Incorrect  Correct ___ Incorrect

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Why are nucleic acids considered acidic? They DO NOT HAVE a carboxyl group like we
see in amino acids -- so WHY are they considered acidic and therefore so named?

Check out the information on the following few pages – read slowly and carefully:

1) We begin with the nitrogenous bases (so-called because they are particularly rich in N):

Purines (double-ringed) Here is adenine (Vic, notice the Here is guanine:

presence of an amine group on C-6):
Here is the generic
structure:

Pyrimidines (single-ringed) Here is cytosine: Here is thymidine: Here is uracil:

Here is the generic
structure:

HW5 A NUCLEIC ACID SEQUENCE

Consider the following nucleic acid sequence: 5’ CCU GAU GGC 3’

Which of the following is accurate about the sequence?

I. It contains both pyrimidine and purine bases.

II. It contains the pentose deoxyribose.
III. It is single stranded.

A. I and II B is correct. The nucleic acid sequence provided is an RNA sequence (we know
this because of the presence of the pyrimidine URACIL (U). RNA contains the
B. I and III pentose RIBOSE (deoxyribose is present only in DNA) so statement II is not
accurate. Furthermore, RNA is single-stranded, making statement III accurate.
C. II and III Finally, the presence of C and U guarantees pyrimidine bases and the presence of
D. I, II, and G
IIIand A guarantees purine bases so statement I is accurate.

2) We continue with the NUCLEOSIDES which now include the sugar component:
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 Vic, notice the change in names:
 adenine and guanine are now adenosine and guanosine
 thymine is now thymidine.
 cytosine is now cytidine.
 uracil is now uridine.

3) When we take a nucleoside and connect ONE or MORE

phosphate groups, we now have a nucleotide (see figure to
the right)  FYI: a nucleotide is WEAKLY BASIC. WHY?

The weak basicity of a nucleotide stems from its

nitrogenous base component. Each N atom possesses a
lone pair of electrons, making the N atom an electron-dense
(or electron-rich) atom and therefore capable of DONATING
AN ELECTRON PAIR – this makes it a Lewis base (in
organic chemistry, we’d refer to it as a nucleophilic N
atom).

4) Finally, nucleotides are joined together through their phosphate groups that form phosphodiester
bonds between the 3’ and 5’ carbon atoms of adjacent sugar rings. This polymer is what we know as
DNA:
In the simple, 4-nucleotide DNA shown to the left, from TOP to
BOTTOM, the nucleosides are:

Thymidine, Adenosine, Cytidine, and Guanosine.

So, after this long introduction, the acidity of DNA is caused by the
presence of the phosphate groups which are themselves acidic. You
can see this by comparing the structure of DNA to that of Phosphoric
acid (below to the right):
WORD BANK: (four of these will be used): hydrogen, strong,
positive, ether, negative, weak, ester, covalent

Vic, if we compare the structures of

phosphoric acid (a weak acid) and
a short strand of DNA, we see that two
protons of phosphoric acid in DNA have been replaced by C atoms (one C atom
is in the ring at the 3’ position and the other C atom is attached to the 5’ C
atom of an adjacent pentose). In chemical terms, this LINK of two C atoms via
a P atom is called a phosphate ester. In the DNA, there is ONE REMAINING
H atom on the single bonded OH group; this proton is now QUITE acidic and
easily lost. In fact, under neutral conditions, DNA is deprotonated at this site,
and the oxygen atom bears a negative charge. Additionally, the nitrogenous
bases do give DNA basic character, but this basic character is masked by the
hydrogen bonding that exists between bases on complementary strands.
Thus, the remaining OH group of the phosphate group dominates and gives
DNA its acidic nature – it is a nucleic acid because it has nucleosides that
have been connected via acidic phosphates. WHOO HOO!
SECTION 1: ACIDS and BASES - A Brief Overview
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 Vic, what you should already know:
From the earliest days of experimental chemistry, scientists have recognized acids and bases by
their characteristic properties:

 Acids have a sour taste and cause certain dyes to change color (of course, the color
change is how we commonly TEST for acids in a simple lab setting), whereas
 Bases have a bitter taste and feel slippery (soap is a good example).
NB: A little history: our use of the term base comes from the old English meaning of the
word, “to bring low.” (We still use the word debase in this sense, meaning to lower the
value of something as when cocaine is CUT with baking soda, rendering it impure and
therefore LOWER in value; or when metal alloys are formed, resulting in a LOWERING IN
VALUE of the more expensive metal – think GOLD ALLOYS.)

So how does this idea of “LOWERING” apply to a chemistry base?

When a base is added to an acid, the base “lowers” the amount of acid. Indeed, when acids
and bases are mixed in the right proportions, their characteristic properties seem to
disappear altogether  we refer to this as neutralization.

HW6 A NEUTRALIZATION
An excess of a carboxylic acid (e.g. ethanoic acid – more commonly known as acetic acid) is
reacted with a specific amount of aqueous sodium hydroxide (NaOH (aq)). Which of the following is
most correct explanation of what happens during the reaction?

A. The carboxylic acid releases a proton (H+) which is abstracted from solution by the sodium
hydroxide base resulting in the species RCOO- and NaOH2+ which creates a neutral solution with
pH = 7
B. The carboxylic acid releases a proton (H+) which is abstracted from solution by the hydroxide
group base resulting in the species RCOO- and H2O which creates a basic solution with pH
greater than 7
C. The carboxylic acid releases a proton (H+) which is abstracted from solution by the hydroxide
group base resulting in the species RCOO- and H2O and OH- which creates a basic solution with
pH equal to 7
D. The carboxylic acid releases a proton (H+) which is abstracted from solution by the hydroxide
group base resulting in the species RCOO- and H2O and H+ which creates an acidic solution with
pH less than 7
D is correct. Sodium hydroxide is a very strong base that readily dissociates into Na + and OH-. Furthermore,
the carboxyl group H atom is released and connects with the OH - to form water. Because there is an
EXCESSS of acid, all of the hydroxide will be neutralized, and any remaining acid will drop the pH to < 7.
By 1830 it was evident that all acids contain hydrogen but not all hydrogen-containing substances are
acids.

GOTTA LOVE THE HISTORY OF THIS DISCIPLINE: In the 1880s, the Swedish chemist Svante
Arrhenius (1859–1927) defined acids as substances that produce H+ ions in water and bases as
substances that produce OH- ions in water.

Victoria, do you think these DEFINITIONS of acids and bases sufficient for ALL chemistry?
Your answer here (be brief, but specific, please): Unfortunately for Arrhenius, THEY ARE NOT
SUFFICIENT! The fact is that there are many chemicals that are acidic in nature and are so in
solvents other than water. The Arrhenius definition is limiting in that sense.

Over time the Arrhenius concept of acids and bases came to be stated in the following way:

 An acid is a substance that, when dissolved in water, increases the concentration of H+ ions.

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 (but not necessarily by just RELEASING H+ ions into the water).

 A base is a substance that, when dissolved in water, increases the concentration of OH- ions.
(again, not necessarily by just RELEASING OH- ions into the water).

Vic, remember the Group 7 halogens: F2 (g), Cl2 (g), Br2 (l), and I2 (s).

Notice that they are ALL DIATOMIC, that fluorine and chlorine are gases at room temperature, while
bromine is a liquid at room temperature, and iodine is a solid at room temperature.

It turns out that the chlorine, bromine, and iodine, will react with water to form strong acids (which
essentially dissociate completely to form VERY LOW pH solutions).

Hydrogen chloride gas, which is HIGHLY SOLUBLE in water, is an example of an Arrhenius acid. In
other words, when it dissolves in water, HCl (g) becomes HCl (aq) which in turn produces hydrated
H+ and Cl- ions:

HCl ( g ) ���
H O
2 � H+ (aq) + Cl- (aq)
This aqueous solution of HCl is known as hydrochloric acid. Concentrated hydrochloric acid is about
37% HCl by mass and is 12 M in HCl.

HW7 A STRONG ACID

Hydrobromic acid is stronger (more acidic) than hydrochloric acid. The best explanation for this
observation is

A. the Br atom is larger (in atomic radius) than the Cl atom giving it an extra electron shell which
makes it easier to release a proton.
B. the Br atom is larger (in atomic radius) than the Cl atom giving it a larger degree of
polarizability which allows it to manage the negative charge as a conjugate base better than the
Cl atom.
C. the Br atom has more mass than the Cl atom allowing it to delocalize the negative charge as a
conjugate base of HBr better than Cl can as the conjugate base of HCl
D. acidity generally increases down a group on the periodic table

B is correct. Polarizability is the ability of charge to be distorted and maneuvered and

managed. The larger the atom, the more polarizable it is if it takes on excess charge
and the more stable the resulting anion. In the case of the acidity of hydrobromic and
hydrochloric acids, the Br atom is larger than the Cl atom, so when they both become
negatively charged, the larger Br- anion is MORE STABLE. As a result, the parent HBr
acid is MORE ACIDIC than the parent HCl acid.

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