Organic Chemistry pKa Values

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52 Terms

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Alkane (e.g. H3C-CH3)

50+

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Alkene (e.g. H2C=CH2)

42-46

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Ketone (e.g. CH3COCH3)

18-20

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Alkyne (e.g. HC≡CH)

22-26

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Amine (e.g. CH3CH2-NH2 )

38-42

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Alcohol (e.g. CH3CH2-OH)

16-18

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Phenol (e.g. C6H5-OH)

9-11

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Ammonium (protonated amine, e.g. NH4+)

9-11

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CH3CO2-H (Acetic acid)

4.76

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Carboxylic Acid

4-5

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Hydronium (protonated water, H3O+)

-1.74

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Protonated Oxygen (alcohol, ketone, aldehyde, ester)

~ -2

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H-Cl

-7

14
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H-I

-9

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H2SO4 (Sulffuric Acid)

-10

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Large pKa → weak acid

weak acid → strong conjugate base

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Strength of Acid

Stronger acid → Weaker CB

Weaker acid → Stronger CB

Acid-base rxns favor the weaker acid and the weaker base

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Lewis Bases (Nucleophiles)

Have availiable electrons that can be donated to form a new bond

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Lewis Acids (Electrophile)

Accept electrons to form new bonds

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Alkanes

  • CnH2n+2

  • Single bonds between the carbons (all carbons are sp3)

  • Low boiling point → Gases

<ul><li><p>C<sub>n</sub>H<sub>2n+2</sub></p></li><li><p>Single bonds between the carbons (all carbons are sp3)</p></li><li><p>Low boiling point → <em>Gases</em></p></li></ul><p></p>
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Constitutional Isomers

Compounds with the same molecular formula but the carbons are connected differently

<p>Compounds with the same molecular formula but the carbons are connected differently </p>
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Cycloalkanes

sp3 carbons form a ring

<p>sp3 carbons form a ring</p>
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Alkenes

Double bonds are present in the molecule (sp2 carbons)

<p>Double bonds are present in the molecule (sp2 carbons)</p>
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Cycloalkenes

Double bond in ring

<p>Double bond in ring</p>
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Alkynes

Triple bonds are present (sp carbons)

<p>Triple bonds are present (sp carbons)</p>
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Aromatic Hydrocarbons

Contains a benzene ring

<p>Contains a benzene ring</p>
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methane

1 Carbon

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Ethane

2 Carbons

29
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Propane

3 Carbons

30
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Butane

4 Carbons

31
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Pentane

5 Carbons

32
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Hexane

6 Carbons

33
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Heptane

7 Carbons

34
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Octane

8 Carbons

35
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Nonane

9 Carbons

36
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Decane

10 Carbons

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Alcohols

Hydroxyl Group is the main functional group

<p><strong>Hydroxyl Group</strong> is the main functional group</p>
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Ethers

Contain 2 alkyl groups bonded to an oxygen

<p>Contain <strong>2 alkyl groups</strong> bonded to an <strong>oxygen</strong></p>
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Aldehydes and Ketone

Contain carbonyl group (C==O)

<p>Contain <strong>carbonyl group </strong>(C==O)</p>
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Carboxylic Acids

Contain the Carboxyl Group (-COOH)

<p>Contain the <strong>Carboxyl Group </strong>(-COOH)</p>
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Amines

Alkylated derivatives of ammonia

<p>Alkylated derivatives of ammonia</p>
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Amides

Derivatives that result from a combination of an acid with ammonia or an amine

<p>Derivatives that result from a combination of an acid with ammonia or an amine</p>
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Nitriles

Contain the cyano group (C≡N)

<p>Contain the cyano group <span>(C≡N)</span></p>
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Bronsted-Lowry Acids

Donate a proton

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Brownster-Lowry Bases

Accept a proton

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Effect of Electronegativity on pKa

More electronegative element bears a negative charge more easily, giving a more stable conjugate base and stronger acid

<p>More electronegative element bears a negative charge more easily, giving a more stable conjugate base and stronger acid</p>
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Atom Effect on pKa

Negative charges of an anion are more stable on larger atoms

Acidity increases down the column on periodic table

<p>Negative charges of an anion are more stable on larger atoms</p><p>Acidity increases down the column on periodic table</p>
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Aufbau Principle

Fill the lowest energy orbitals first

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Hund’s Rule

When there are two or more orbitals of the same energy (degerate), electrons will go into different orbitals rather than pairing up in the same orbital

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Bond Formation

Conbining orbitals between two different atoms

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Hybridization

Combining orbitals on the same atom