Chapter 4: Covering the Bases (And the Acids)

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Equilibria

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42 Terms

1

Equilibria

________ favor the reaction side with the lowest- energy species; acid- base reactions will go to the side with the weakest acids and bases.

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2

electronegative fluorine atoms

The highly ________ on trifluoroethanol pull electron density away from the anion, taking away some of the negative charge from the oxygen, thereby stabilizing the molecule.

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3

Hydrogen cyanide

________ (pKa= 9) has a higher pKa value than acetic acid (pKa= 5), the equilibrium will lie to the left, in the direction of the weaker acid and base.

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4

conjugate base

Electron- withdrawing groups on an acid also stabilize the ________ anion by allowing some of the charge on the anion to delocalize to other parts of the molecule.

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5

BH3

Because ________ accepts a pair of electrons to make a covalent bond, its said to be a Lewis acid.

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6

Lewis

________ acid: molecule that accepts a pair of electrons to make a covalent bond.

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7

nucleophiles

Also called ________: molecules that can donate electrons (Lewis bases) to form bonds and are nucleus lovers.

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8

electrophiles

Also called ________: molecules that can accept electrons (Lewis acids) to make a new bond and are electron lovers.

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9

Lone pair anions

________ prefer to reside in orbitals that have more s character than p character, because s orbitals are closer to the atoms nucleus than p orbitals, and the electrons are stabilized by being closer to the nucleus.

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10

Arrhenius acids

________: molecules that dissociate in water to make the hydronium ion, H3O+.

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11

PKa value

________ of an acid: a quantitative measurement of a molecules acidity.

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12

Borane doesnt

________ have a full octet of valence electrons Because it doesnt have a full octet of electrons, it can accept a lone pair from a molecule like methylamine (CH3NH2), which has a lone pair of electrons, and use this electron pair to fill its octet.

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13

Borane

________ (BH3) is an example of a Lewis acid.

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14

Arrhenius bases

________: molecules that dissociate to make hydroxide ions, OH-

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15

conjugate bases

Acids with ________ that allow the negative charge to be delocalized through resonance are stronger acids than acids whose ________ dont have resonance structures.

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16

Arrhenius acids and bases

A little watery

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17

Arrhenius acids

molecules that dissociate in water to make the hydronium ion, H3O+

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18

Strong Arrhenius acids

completely dissociate in water to make hydronium ions

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19

Example

Nitric acid (HNO3) is a strong acid because it completely dissociates in water to make hydronium ions

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20

Weak Arrhenius acids

acids that only partially dissociate in water

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21

Example

Acetic acid (CH3COOH) only partially dissociates in water and is a weak acid

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22

Arrhenius bases

molecules that dissociate to make hydroxide ions, OH-

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23

Strong Arrhenius bases

bases that dissociate completely to generate hydroxide ions

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24

Example

Potassium hydroxide (KOH) is a strong base because it completely dissociates in water to make hydroxide ions

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25

Weak Arrhenius bases

bases that only partially dissociate to generate hydroxide ions

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26

Example

Beryllium hydroxide (Be[OH]2) is a weak base because it only partially dissociates in water

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27

Pulling for protons

Brønsted-Lowry acids and bases

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28

Brønsted-Lowry acid

molecule that donates a proton (H+) to a base

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29

Brønsted-Lowry base

molecule that accepts a proton from an acid

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30

Conjugate base

what the deprotonated acid becomes

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31

Conjugate acid

what the protonated base becomes

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32

Electron lovers and haters

Lewis acids and bases

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33

Lewis acid

molecule that accepts a pair of electrons to make a covalent bond

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34

Also called electrophiles

molecules that can accept electrons (Lewis acids) to make a new bond and are electron lovers

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35

Lewis base

molecule that donates electrons to make a covalent bond

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36

Also called nucleophiles

molecules that can donate electrons (Lewis bases) to form bonds and are nucleus lovers

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37

Note

Any Brønsted acid will also be a Lewis acid, and any Brønsted base will also be a Lewis base

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38

Example

Fluorine is a more electronegative atom than iodine, HI is more acidic than HF

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39

Example

Trifluoroethanol is more acidic than ethanol

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40

Example

acetic acid is much more acidic than ethanol because the conjugate base anion of acetic acid can delocalize the negative charge through resonance

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41

pKa value of an acid

a quantitative measurement of a molecules acidity

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42

Example

Predict the direction of the acid-base reaction between hydrogen cyanide (HCN) and acetate (C2H3O2-)

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