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MCAT CHEM-PHY > Organic Chemistry > Flashcards

Organic Chemistry Flashcards

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1
Q

Acid and Bases: Lewis Acid:

A

e- acceptor. Has vacant orbitals or + polarized atoms

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2
Q

Acids and Bases: Lewis Base

A

e- donor. Has a lone pair of e-, are often anions

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3
Q

Acids and Bases: Brønsted-Lowry Acid:

A

Proton donor

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4
Q

Acids and Bases: Brønsted-Lowry Base

A

Proton acceptor

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5
Q

Acids and Bases: Amphoteric

Molecules

A

Can act as either acids or bases, depending on

reaction conditions.

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6
Q

Acids and Bases: Ka

A

Acid dissociation constant. A measure of acidity. It is
the equilibrium constant corresponding to the
dissociation of an acid, HA, into a proton and its
conjugate base.

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7
Q

Acids and Bases : pKa

A

An indicator of acid strength. pKa decreases down the
periodic table and increases with EN.
p𝐾a = −log (𝐾a)

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8
Q

Acids and Bases: a-carbon

A

A carbon adjacent to a carbonyl.

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9
Q

Acids and Bases: a-hydrogen

A

Hydrogen connected to an a-carbon.

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10
Q

Redox Reactions: Oxidation Number

A

The charge an atom would have if all its bonds were

completely ionic.

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11
Q

Redox Reactions: Oxidation:

A

Raises oxidation state. Assisted by oxidizing agents.

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12
Q

REDOX Reactions: Oxidizing Agent:

A

Accepts electrons and is reduced in the process

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13
Q

Redox Reactions: Reduction

A

Lowers oxidation state. Assisted by reducing agents

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14
Q

Redox Reactions: Reducing Agent

A

Donates electrons and is oxidized in the process

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15
Q

Solvents: Polar Protic

A

Polar Protic solvents
Acetic Acid, H2O,
ROH, NH3

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16
Q

Sovents Polar Aprotic

A

Polar Aprotic solvents
DMF, DMSO,
Acetone, Ethyl Acetate

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17
Q

Nucleophiles:

A

“Nucleus-loving”. Contain lone pairs or p bonds. They have (arrow up)
EN
and often carry a NEG charge. Amino groups are
common organic nucleophiles

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18
Q

Nucleophilicity

A

A kinetic property. The nucleophile’s strength. Factors that
affect nucleophilicity include charge, EN, steric hindrance,
and the solvent

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19
Q

Electrophiles

A

“Electron-loving”. Contain a + charge or are positively

polarized. More positive compounds are more electrophilic

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20
Q

Leaving Group:

A

Molecular fragments that retain the electrons after
heterolysis. The best LG can stabilize additional charge
through resonance or induction. Weak bases make good LG

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21
Q

SN1 Reactions:

A

Unimolecular nucleophilic substitution. 2 steps. In the 1st
step, the LG leaves, forming a carbocation. In the 2nd step,
the nucleophile attacks the planar carbocation from either
side, leading to a racemic mixture of products.
Rate = 𝑘 [substrate]

22
Q

SN2 Reactions

A

Bimolecular nucleophilic substitution. 1 concerted step. The
nucleophile attacks at the same time as the LG leaves. The
nucleophile must perform a backside attack, which leads to
inversion of stereochemistry. (R) and (S) is also changed if
the nucleophile and LG have the same priority level. SN2
prefers less-substituted carbons because steric hindrance
inhibits the nucleophile from accessing the electrophilic
substrate carbon.
Rate = 𝑘 [nucleophile] [substrate]

23
Q

Alcohols:

A

Have the general form ROH and are named with the suffix –ol.
If they are NOT the highest priority, they are given the prefix
hydroxy

Alcohols can hydrogen bond, raising their boiling and melting
points

24
Q

Phenols:

A

Benzene ring with –OH groups attached.

Phenols are more acidic than other alcohols because the
aromatic ring can delocalize the charge of the conjugate base

25
Q

Describe the structure of a phenol ( (ortho)

A
26
Q

Describe the structure of a phenol (meta)

A
27
Q

Describe the structure of a phenol (para)

A
28
Q

Reactions of Alcohols : Primary

Alcohols

A

Can be oxidized to aldehydes only by pyridinium
chlorochromate (PCC); they will be oxidized all the way to
carboxylic acids by any stronger oxidizing agents

29
Q

Reactions of Alcohols : Secondary

Alcohols

A

Can be oxidized to ketones by any common oxidizing agent

30
Q

Alcohols can be converted to make better leaving groups and the groups are

A

Mesylates

Tosylates

31
Q

Mesylates:

A

Contain the functional group –SO3CH3

32
Q

Tosylates

A

Contain the functional group –SO3C6H4CH3

33
Q

Infrared Spectroscopy - IR range and Peaks N-H

A

Range 3300 peak Sharp

34
Q

Infrared Spectroscopy - IR range and Peaks O-H

A

3000-3300 - Broad

35
Q

Infrared Spectroscopy - IR range and Peaks C triple bond N

A

1900 – 2200 Medium

36
Q

Infrared Spectroscopy - IR range and Peaks C=0

A

1750 Sharp

37
Q

Infrared Spectroscopy - IR range and Peaks C=C

A

1600-1680 Weak

38
Q

Solubility-Based Methods - Extraction:

A

Combines two immiscible liquids, one of which easily

dissolves the compound of interest.

39
Q

Solubility-Based Methods - Extraction: Nonpolar Layer

A

Organic layer, dissolves nonpolar

compounds.

40
Q

Solubility-Based Methods - Extraction: Polar Layer

A

Aqueous (water) layer. Dissolves

compounds with hydrogen bonding or polarity

41
Q

Solubility-Based Methods — Wash

A

The reverse of an extraction. A small amount of
solvent that dissolves impurities is run over the
compound of interest.

42
Q

Solubility-Based Methods (filtration)

A

Isolates a solid (residue) from a liquid (filtrate)

43
Q

What are the two filtration methods

A

Gravity Filtration:

Vacuum Filtration

44
Q

Solubility-Based Methods : Gravity Filtration

A

Use when the product of interest is
in the filtrate. Hot solvent is used to maintain
solubility.

45
Q

Solubility-Based Methods : Vacuum Filtration

A

Used when the product of interest
is the solid. A vacuum is connected to the flask to pull
the solvent through more quickly.

46
Q

Solubility-Based Methods : Recrystallization:

A

The product is dissolved in a minimum amount of hot
solvent. If the impurities are more soluble, the
crystals will reform while the flask cools, excluding the
impurities

47
Q

Chromatography

A

Separates two or more molecules from a mixture. Includes liquid
chromatography, gas chromatography, size-exclusion chromatography,
ion-exchange chromatography, affinity chromatography, and thin-layer
chromatography

48
Q

Distillation

A

Separates liquids according to differences in their boiling
points. The liquid with the lowest BP vaporizes first and is
collected as the distillate

49
Q

Simple

Distillation

A

Can be used if the boiling points are under 150°C and are at

least 25°C apart

50
Q

Vacuum

Distillation

A

Should be used if the boiling points are over 150°C to
prevent degradation of the product. The vacuum lowers
the air pressure, which decreases the temp the liquid must
reach in order to boil

51
Q

Fractional

Distillation

A

Should be used if the boiling points are less than 25°C apart
because it allows more refined separation of liquids by BP

MCAT CHEM-PHY (2 decks)

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