Chapter 3 Flashcards

1
Q

What is the Bronsted/Lowry definition of acids/bases?

A

Base is a proton acceptor, acid is a proton donor

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2
Q

What is the Lewis definition of acids/bases?

A

Base is an electron pair donor, acid is a electron pair acceptor

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3
Q

What is a nucleophile?

A

Electron pair donor to an atom other than hydrogen

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4
Q

What is a electrophile?

A

An electron pair acceptor

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5
Q

How do you get conjugate acids or bases?

A

Base (or any species) + H+ -> Conjugate acid

Acid (or any species) - H+ -> Conjugate base

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6
Q

When do you use the size of atoms to determine the strength of acids? How does that work?

A

Use when comparing atoms of the same column, Do not use when atom is not directly connected to the breaking bond

Strength of acids increases as you go down
Bigger atoms have longer bonds that are easier to break

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7
Q

When do you use electronegativity to determine the strength of acids? How does that work?

A

Use when comparing atoms of the same row/period

Strength of acids increases from left to right
Atoms with greater electronegativity will pull electrons towards themselves and weaken the bond to the hydrogen

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8
Q

When do you use hybridization to determine the strength of acids? How does that work?

A

Use when the atom binding to the hydrogen is the same

Find the weakest conjugate base (electrons in lowest energy)
Lower hybridization (sp->sp2->sp3)
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9
Q

When do you use inductive effects to determine the strength of acids? How does that work?

A

Use when comparing certain atoms or groups (ex: carbonyl groups)

Greater the inductive effect means a weaker bond holding the H
The stronger and closer the electronegative thing is, the stronger the acid

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10
Q

When do you use resonance to determine the strength of acids? How does that work?

A

Use when determining the strength of bases (including conjugate bases)

The more stable it is (greater resonance structures) the weaker
More structures-> more stable-> weaker base-> stronger acid

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11
Q

When do you use the solvent effect to determine the strength of acids? How does that work?

A

Acids are stronger in polar protic solvents

Protic solvents are those that have a H attached to N, O, or F
Solvation prevents recombination-> equilibrium to the right-> stronger

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12
Q

How do you choose a reactant and solvent for a reaction?

A

Whenever a solvent is used, it must be checked to be sure that it will not react

When choosing a reactant, make sure weaker acids/bases are produced

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13
Q

What is a deuterium? What is a tritium?

A

One proton is a hydrogen
One proton, one neutron is a deuterium
One proton, two neutrons is a tritium

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14
Q

What sort of charge does a nucleophile need?

A

an overall negative charge, or a delta - charge

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15
Q

What sort of charge does a electrophile need?

A

an overall positive charge, or a delta + charge

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16
Q

What are the two acid strength arguments where you need to look at the conjugate base?

A

Hybridization and resonance

17
Q

Describe the two step process for making a deuterated or tritiated compound

A

Make a Base-Li by combining the corresponding alkyl halide with Li (LiH, or NaH, usually)
Take the base (which is not really bonded with the Li) and add D/T
For the base to react, the D/T must be +, so it needs to be in D/H2O