Return to Contents Chapter 1: Structure Determines Properties Ch 1 contents


Acids and Bases

Your organic teachers are quite likely to ask you questions
like identify the most acidic protons or the most basic site
in a molecule.  These facts can be important for determining where
a molecule is likely to react when treated with a base or acid respectively.
Many students can not do this efficiently. The following topics are covered
here:

  • Definitions : Arrenhius,
    Bronsted, Lewis
  • Acidity :  Ka
    and pKa
  • Common acids in organic chemistry
  • Basicity
  • Common bases in organic chemistry

Remember that acidity and basicity are the based on the same
chemical reaction (but looking at it from opposite sides) and both happen simultaneously.
In the following simple example the base, B,
removes a proton from the acid, H-A:

a simple acid-base reaction

QUESTION : Can you think
of another type of reaction that involves opposites simultaneously ?  ANSWER

Definitions
There are three theories used to describe acids and bases :
 


Acids Bases
Arrenhius Ionise to give H+ in
H2O
Ionise to give HO
in H2O
Bronsted-Lowry A proton donor A proton acceptor
Lewis An electron pair acceptor An electron pair donor

Now, some terminology:


terminology

Look at this equation and see how it fits the Bronsted-Lowry
and Lewis definitions.

Acidity
Here are some general guidelines of principles to look for that can help you
address the issue of acidity:
First, consider the simplified general equation of a simple acid reaction:

equation defining Bronsted acidity
equation that defines K<sub>a</sub> 
equation that defines pK<sub>a</sub>

  • The more stable the conjugate base, A,
    is then the more the equilibrium favours the product side (Ka > 1), i.e.
    more dissociation of HA
  • More dissociation of HA then the stronger HA
    is as an acid, or
  • The more the equilibrium favours products, the more H+
    there is….
  • The more H+ there is then the stronger
    HA is as an acid….
  • So looking for factors that stabilise the conjugate
    base, A, gives us a “tool” for assessing
    acidity.
  • The larger Ka implies more dissociation of
    HA and so the stronger the acid.
  • The larger Ka is, the more negative the pKa
    so the lower the pKa, the stronger the acid.

Key factors that affect the stability of the conjugate base,
A
,
 



HF > H2O > NH3 >
CH
Electronegativity.  When comparing atoms
within the same row of the periodic table, the more electronegative
the anionic atom in the conjugate base, the better it is at accepting
the negative charge.


HI > HBr > HCl > HF Size.  When comparing atoms within
the same group of the periodic table
, the easier it is for the conjugate
base to accommodate negative charge (lower charge density). The size of
the group also weakens the bond H-X (note this trend should be
applied with care since it only works within a group).


RCO2H > ROH Resonance.  In the carboxylate ion, RCO2
the negative charge is delocalised across 2 electronegative
oxygen atoms which makes it more stable than being localised on a specific
atom as in the alkoxide, RO.

General acidity trend of common
organic acids
(this is a very useful sequence to remember and to
be able to rationalise):

acidity of common organic functional groups

Basicity
A convenient way to look at basicity is based on electron pair availability….
the more available the electrons, the more readily they can be donated to form
a new bond to the proton and, and therefore the stronger base.

Key factors that affect electron pair availability in a
base
, B



CH3  >
NH2> HO > F
Electronegativity.  When comparing atoms
within the same row of the periodic table, the more electronegative the
atom donating the electrons is, the less willing it is to share those
electrons with a proton, so the weaker the base.


F> Cl–  >
Br–  > I– 
Size. When comparing atoms within the same group
of the periodic table, the larger the atom the weaker the H-X bond
and the lower the electron density making it a weaker base.


 RO  > 
RCO2– 
Resonance.  In the carboxylate ion, RCO2
the negative charge is delocalised across 2 electronegative
atoms which makes it the electrons less available than when they localised
on a specific atom as in the alkoxide, RO.

General acidity trend of some
common organic bases:

Note that organic chemists tend to think about bases by looking at the pKa’s of their conjugate acids, i.e. think about B- by looking at the acidity of BH. The implications are that the higher the pKa of the related conjugate acid, BH, the stronger the baseb B-.


pKa data for some common organic bases


Study Tip: Note
that acidity and basicity are just the reverse of each other.

AND
Therefore, both are affected by the same factors, just in opposite
ways.


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© Dr. Ian Hunt ,
Department of Chemistry, University of Calgary

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Walkthrough of Acid Base Reactions (2): Basicity

by James

in Organic Chemistry 1 , Organic Reactions , Understanding Electron Flow

Last time I started writing about acid-base reactions. We looked at this list of stabilities of anions going across the topmost row of the periodic table.

 Fluoride ion is the most stable in this series because it’s the most electronegative; carbon is the least stable because it’s the least electronegative.

Because of this, we were able to say that H-F was the most acidic, because it had the most stable conjugate base.

And H-CH3 (methane)was the least acidic, because it had the least stable conjugate base.

Let’s look at the flip side of this reaction. Instead of starting with HF, H2O, H3N, and CH4 and asking how likely they are to donate a proton to a common base (water in our example) , imagine we start with the anions [ F-, HO-, H2N- and H3C- ] and have them take a proton away from  a common acid (such as water).

Which reactions would be most favorable? Which would be least favorable?

The same principle applies. The less stable the anion, the more likely the reaction will be to proceed to completion. 

So in this case, the reaction of F- with H2O would be the least favored, because F- is the most stable. And the reaction of H3C- with H2O would be the most favored, becuse H3C- is the least stable.

[A clarification: these are equilibrium reactions. So what I mean by favored here is the extent to which the equilibrium would favor the products on the right]

Notice the role that each of these anions plays in these reactions: it is accepting a proton from water, so in other words it is acting as a base.

Therefore, our whole discussion of the  “stability” of anions,  for lack of a better term, goes by another name you’re familiar with: basicity. 

In other words:

  • the more stable a lone pair of electrons is, the less basic it will be.
  • the less stable a lone pair of electrons is, the more basic it will be.

 

Let’s tie these two posts together with a common thread:

  •  For any group of acids, H-X (where X can literally be anything), the strongest acid will have the most stable conjugate base. Since stability is inversely correlated with basicity, another way of putting it is:
  • The stronger the acid, the weaker the conjugate base.
  • Today’s post is about how the opposite is also true: The weaker the acid, the stronger the conjugate base.

Next time, we’ll apply this framework to other stability trends we’ve discussed previously.

 

P.S. One last note: a common misconception students have is that “weak acids are strong bases”. Not true! Methane (CH4) is a weak acid, but it can’t act as a base – it doesn’t have a lone pair.

The proper way to say it is that “weak acids have strong conjugate bases”. So the conjugate base of CH4, CH3(-) is an extremely strong base.

Next Post: Walkthrough of Acid-Base Reactions (3) – Acidity Trends

Related Posts:

  • Walkthrough of Acid-Base Reactions (3) – Acidity Trends
  • How to Use a pKa Table
  • A Handy Rule of Thumb for Acid-Base Reactions
  • Walkthrough of Acid-Base reactions (4) – pKa

Tagged as:
acids ,
anions ,
bases ,
basicity ,
conjugate acid ,
conjugate base ,
pka ,
stability ,
trends

7 comments… read them below or add one


Paul

THIS SITE IS GREAT!!! I couldn’t find videos on Khan Academy but this had a ton of info and it was explained in a way I could understand! Thanks a ton!

Reply


ibrahim

I appreciate your a great work . Today I learnt what mean acid base reaction

Reply


Aniqa

This is an incredible site! I really appreciate your hard work and all the effort you put into this. Studying from your site has drastically increased my marks in organic chemistry at university and I totally owe it all to you! Thank you once again! 😀

Reply


Jane Lee

Thank you so much for the explanation! It has helped me a lot 🙂
However I still cannot figure out which one is a stronger base between -OH and -OC(CH3)3..

Reply


James

They’re quite similar, but t-butoxide is a bit more basic, mostly because the oxygen of the t-butoxide won’t be able to accept as many hydrogen bond donors as hydroxide (and hence be more “unstable”)

Reply


Bertin

Please help me classify the following in order of increasing basicity..
Aniline, 2-Toluene, dinitribenzene and 4-chloroaniline

Reply


James

When nothing is mentioned which medium should i consider while determining basicity of amines?

Reply

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    • Synthesis (3) – Figuring Out The Order
    • Synthesis Part 1
    • Synthesis Study Buddy
    • Synthesis: Walkthrough of A Sample Problem
    • Synthesis: Working Backwards
    • t-butyl
    • Tautomerism
    • The Awesomeness Of The SN2
    • The Claisen Condensation
    • The E1 Reaction
    • The Inflection Point
    • The Meso Trap
    • The Michael Reaction
    • The Nucleophile Adds Twice (to the ester)
    • The One-Sentence Summary Of Chemistry
    • The Second Most Important Carbonyl Mechanism
    • The Single Swap Rule
    • The SN1 Reaction
    • The SN2 Reaction
    • The Wittig Reaction
    • Three Exam Tips
    • Tips On Building Molecular Orbitals
    • Top 10 Skills
    • Try The Acid-Base Reaction First
    • Two Key Reactions of Enolates
    • Welcome
    • What makes a good leaving group?
    • What Makes A Good Nucleophile?
    • What to expect in Org 2
    • Work Backwards
    • Zaitsev’s Rule
  • Tuesday Oct 22 Acid Base Webinar at 9pm EST
  • Videos
    • A Simple Trick For Determining R/S
    • Applying E2 Reactions with Newman Projections
    • Bond Rotations: Exercise 1
    • Bond Rotations: Exercise 2
    • Bond Rotations: Exercise 3
    • Bond Rotations: Exercise 4
    • Bond Rotations: Exercise 5
    • Bond Rotations: The “Steering Wheel” Analogy
    • Bronsted and Lewis Acidity
    • Bulky Bases in Elimination Reactions
    • Carbocation Stability
    • Comparing E1 and E2 Mechanisms
    • Comparing E1 and E2 Stereochemistry
    • Comparing the E1 and SN1
    • Comparing the SN1 and SN2
    • Converting a Fischer Projection To A Line Diagram
    • Converting a Line Diagram to a Fischer Projection
    • Converting a Newman Projection to a Line Diagram
    • Curved Arrows
    • Determining R/S on a Fischer Projection
    • E1 with Rearrangement
    • E1 With Rearrangement (2)
    • Elimination Exercise: Zaitsev’s Rule
    • Elimination Reactions in Cyclohexanes
    • Elimination Reactions in Cyclohexanes (2)
    • Evaluating Resonance Forms (1) Charges
    • Evaluating Resonance Forms (2) Octets
    • Evaluating Resonance Forms (3) Negative Charge
    • Evaluating Resonance Forms (4) Positive Charge
    • Evaluating Resonance Forms (5) Aromaticity
    • Exercise: Condensed Formula (1)
    • Exercise: Condensed Formula (2)
    • Factors that affect acidity – Aromaticity
    • Factors That Affect Acidity (1) Charge Density
    • Factors That Affect Acidity (2) Electronegativity
    • Factors That Affect Acidity (3) Polarizability
    • Factors That Affect Acidity (4) Electron Withdrawing Groups
    • Factors That Affect Acidity (4) Resonance
    • Factors That Affect Acidity (6) – Orbitals
    • Formal Charge (1) – Atomic Charge
    • Formal Charge (2) – Introduction to Formal Charge
    • Formal Charge Exercise: Allyl Carbocation
    • Formal Charge Exercise: CH2N2
    • Formal Charge Exercise: CH3NO2
    • Formal Charge Exercise: CN
    • Formal Charge Exercise: CO3
    • Formal Charge Exercise: Hidden Hydrogens
    • Formal Charge Exercise: Hidden Lone Pairs
    • Formal Charge Exercise: N3
    • Formal Charge Exercise: NH4
    • Formal Charge Exercise: O3
    • Formal Charge Exercise: Radicals and Carbenes
    • Hidden Hydrogens
    • How Formal Charge Can Mislead
    • How Heat Affects Elimination Reactions
    • How to draw an enantiomer
    • How To Use A pKa Table
    • In Summary: Resonance
    • Introduction to Elimination
    • Introduction to pKa
    • Introduction to Rearrangements
    • Introduction to Resonance
    • Introduction to the E2 Reaction
    • Introduction to the SN1: Experiments
    • Introduction to the SN2: Experiments
    • Key Patterns in Formal Charge
    • Line Drawings
    • Making OH Into A Good Leaving Group
    • Rearrangement Reactions: Alkyl Shifts
    • Rearrangement: Hydride Shift
    • Rearrangements: Carbocation Stability
    • Resonance – Common Mistakes (1)
    • Resonance – Common mistakes (2)
    • SN1 Exercise: The Substrate
    • SN1 Reaction Energy Diagram
    • SN1 vs. SN2 Overview
    • SN1 With Alkyl Shift (1)
    • SN1 With Alkyl Shift (2)
    • SN1 With Hydride Shift
    • SN1: Applying the SN1 Reaction
    • SN1/SN2/E1/E2 – Substrate
    • SN1/SN2/E1/E2 Decision – Overview
    • SN1/SN2/E1/E2 Decision – Solvent
    • SN1/SN2/E1/E2 Decision – Temperature
    • SN1/SN2/E1/E2 Decision – The Nucleophile/Base
    • SN2 Exercise: Apply the SN2
    • SN2 Exercise: Leaving Groups
    • SN2 Exercise: The Substrate
    • Solvents in SN1 and SN2 Reactions
    • Stereochemistry Exercise 1
    • Stereochemistry Exercise 2
    • Stereochemistry Exercise 3
    • Stereochemistry Exercise 4
    • Stereochemistry Exercise 5
    • Strong and Weak Acids
    • Substitution: What is Substitution?
    • The 4 Components of Every Acid Base Reaction
    • The E1 Reaction
    • The Golden Rule of Acid Base Reactions
    • The Single Swap Rule
    • The SN1 Mechanism
    • The SN2 Mechanism
    • The SN2 Reaction Energy Diagram
    • Understanding R/S Relationships
    • Unequal Resonance Forms
    • Using Electronegativity to Find Reactive Sites on a Molecule
    • What Makes A Good Leaving Group?
    • What Makes A Good Nucleophile? (1)
    • What Makes A Good Nucleophile? (2)
    • What Makes A Good Nucleophile? (3)
    • What’s A Nucleophile?
    • Zaitsev’s Rule
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