Mcat Organic

Front 1

List the six important strong acids

Back 1

HCl
HBr
HI
sulfuric acid
nitric acid
Perchloric Acid (HClO4)

Front 2

List strong bases

Back 2

Lithium Hydroxide: LiOH
Sodium Hydroxide: NaOH
Potassium Hydroxide: KOH
Rubidium Hydroxide: RbOH
Calcium Hydroxide: Ca(OH)2
Strontium Hydroxide: Sr(OH)2
Barium Hydroxide: Ba(OH)2
Alkoxide Ions
NaH

Front 3

Solubility Rules

Back 3

Soluble:
All salts of alkali metals
All salts of ammonium
All salts of Nitrate (NO3)-
Cl-, Br-, I- salts are soluble, except with Hg, Ag, Pb.
Sulfate salts are soluble except with Ca Sr Ba and Pb

Insoluble:
Metal Oxides, except alkali metals and CaO, SrO, and BaO, which forms corresponding metal hydroxides
Hydroxides, except with alkali metals and Ca, Sr, Ba
Carbonates, Phosphates, Sulfides, sulfites are insoluble, except alkali metals and ammonium.

Front 4

Electronic Geometry:
Regions of electron density:

2
3
4
5
6

Back 4

2 - linear
3 - trigonal planar
4 - tetrahedral
5 - trigonal bipyramidal
6 - octahedral

Front 5

Reactivity of Carboxylic Acid Derivatives
From most reactive to least reactive

Back 5

1. Acyl Chloride (acid chloride)
2. Anhydride
3. Carboxylic Acid
4. Ester
5. Amide

Front 6

1. Good leaving groups
2. Bad leaving groups

Back 6

1. Chloride anion, carboxylate anion, water(H2O+)
2. Hydroxyl group, alkoxide anion, NH2

Front 7

Electron Donating / Withdrawing Effects
1. Activating (Most to Least
2. Deactivating (Most to Least)

Back 7

1. oxide O-
tertiary amine
secondary amine
primary amine
hydroxyl group
ether
Amide
Ester
alkyl group
benzyl group
vinyl group

2. Nitro group
quaternary amine
ammonium
S=O=O-OH
nitrile
CF3
Acyl Chloride
Carboxylic acid
Ester
Ketone
Aldehyde
Halogen (ortho-para directing)

Front 8

Dehydrohalogenation
1. Type of mechanism
2. What kind of base
3 What kind of substrate
4. What happens

Back 8

1. E2
2. Strong, Bulky
3. Alkyl Halide
4. Strong bulky base is too big to be a nucleophile. So, it rips off a hydrogen. The halide drops off, and alkene is formed. This all occurs in one step.

Front 9

Dehydration of alcohol
1. What kind of reaction
2. Substrate
3. What reaction conditions, intermediate step
4. Product

Back 9

1. E1
2. Alcohol
3. Acid, which protonates the alcohol, makes water, a good leaving group. Leaves carbocation. Rearrangement may occur. Water takes neighboring hydrogen, double bond is formed.
4. alkene. Zaitsev arrangement

Front 10

Catalytic hydrogenation
1. substrate
2. Catalyst, type of catalyst
3. What kind of addition
3. Thermodynamics?

Back 10

addition of h2 to an alkene to form an alkane
1. alkene
2. Pd, heterogeneous
3. syn addition
4. exothermic reaction

Front 11

Oxidation of alkenes:
Ozonolysis
1. What is the oxidizing agent
2. What does it do to an alkene

Back 11

1. Ozone, O3 (high energy)
2. Cleaves right through the double bonds, and bandages them with an O. leaves carbonyl groups.

Front 12

Oxidation of alkenes:
Permanganate and Heat
1. What does it do to an alkene

Back 12

KMnO4 cleaves right through the double bond, and bandages with an O, leaving a carbonyl group. Additionally, it will oxidize any remaining aldehydes to carboxylic acids.

Front 13

Oxidation of alkenes:
Cold Permanganate
1. What does it do to an alkene
2. What is this called?

Back 13

Does NOT cleave right through. Adds a hydroxyl group to both double bonded carbons. Forms a glycol.
2. Hydroxylation

Front 14

Oxidation of alkenes: Addition of Osmic tetroxide (OsO4)
1. What does it do

Back 14

Like KMnO4 in the cold, it forms a glycol.

Front 15

Electrophilic Addition to an Alkene
1. What is generally being added
2. Where does it add
3. What is this addition called

Back 15

1. HBr
2. Most substituted carbon
3. Markovnikov

Front 16

Electrophilic addition to an alkene: Anti-markovnikov
1. What can be done to make the reaction proceed in the anti-markovnikov fashion?
2. Where does the addition of the bromine take place?
3. What is the only thing that can add to an alkene in this fashion?

Back 16

1. Carry out the reaction in the presence of peroxides, or UV light, or oxygen (anything that produces free radicals)
2. Least substituted carbon. Antimarkovnikov (free radical attaches to most substituted carbon)
3. Hydrogen Bromide

Front 17

Oxymercuration Demurcuration
1. What kind of reaction
2. Substrate
3. Reaction conditions
4. orientation

Back 17

1. Electrophilic addition, hydroxylation
2. Alkene
3. HgOAc, NaBH4
4. Markovnikov

Front 18

Hydration of an alkene
1. what is it
2. What are the reaction conditions
3. What kind of reaction (Markovnikov, antimarkovnikov?)
4. This reaction is the reverse of...

Back 18

1. Addition of water to an alkene to form an alcohol
2. Cold, dilute acid
3. Markovnikov addition
4. Dehydration of an alcohol

Front 19

Hydroboration:
1. What it does
2. Reaction conditions

Back 19

1. hydrates an alkene in anti markovnikov addition
2. BH3, H2O2

Front 20

Halogenation of alkenes
1. Reaction conditions
2. Type of reaction
3. Orientation of reaction
4. Interesting intermediate

Back 20

1. Adding X2
2. Electrophilic additions
3. Anti addition
4. Cyclonium ion

Front 21

Grignard Reaction
1. What does it do
2. Reaction conditions

Back 21

1. Adds an alkyl group to a ketone or aldehyde to form an alcohol
2. MrBr+ -R -R acts as a nucleophile

Front 22

Synthesis of alkyl halides using alcohol as a reactant
1. What do you add? What does that do?
2. end product

Back 22

1. HCl or other strong acid to protonate hydroxyl group to make it a good leaving group.
2. alkyl halide.

Front 23

Tautomerization
1. What is the functional group(s) in question
2. Describe how they are acidic
3. How to form enol

Back 23

1. Aldehydes and ketones
2. alpha hydrogen can be donated. Conjugate base is stabilized by partial positive charge of carbonyl carbon
3. Alpha hydrogen jumps to carbonyl oxygen, which takes up two electrons from carbonyl double bond. Electons that originally held the hydrogen form the enol double bond.

Front 24

Nucleophilic addition of alcohol to an aldehyde or ketone
1. What is the nucleophile?
2. What are reaction conditions for first alcohol addition?
3. What is the product?
4. What are the reaction conditions for the second addition of alcohol?
5. What is the product?
6. Cool thing about this reaction?

Back 24

1. Alcohol. One of the lone pairs of electrons on the oxygen attacks the carbonyl carbon. The H drops off and protonates the carbonyl oxygen.
2. Acidic or Basic
3. Alcohol and OR group (hemiacetal or hemiketal)
4. Acidic (must be acidic so hydroxyl group can be protonated and fall off)
5. Carbon with two OR groups(acetal or ketal)
6. It can be reversed just by adding acid, and you get aldehyde or ketone back. Used as a blocking agent, when you want to reduce other groups, like esters, but not aldehydes and ketones.
2.

Front 25

What happens when you mix water with aldehydes and ketones?

Back 25

establish equilibrium with geminal diol.

Front 26

Aldol condensation
1. What category of reaction?
2. What are the reactants?
3. What is the nucleophile?
4. What is the electrophile?

Back 26

1. Nucleophilic addition
2. An aldehyde or ketone reacting with itself, or another aldehyde or ketone
3. A negatively charged alpha carbon after it has released its alpha hydrogen.
4. The carbonyl carbon of the other aldehyde/ketone

Front 27

Decarboxylation:
1. Removal of a...

Back 27

Carboxylate group

Front 28

Fisher esterification
1. What are the reactants
2. What are the reaction conditions
3. What happens
4. Which oxygen is obtained in the product
5. What is the product

Back 28

1. Carboxylic acid and alcohol
2. Acidic
3. Acid protonates the hydroxyl group of the carboxylic acid, making a leaving group.
4. The alcohol oxygen, because its lone pair makes it a lewis base, and it attacks the carbonyl carbon
5. An ester

Front 29

Nucleophilic addition of amine to aldehyde or ketone
1. reaction conditions
2. product
3. tautomerization?

Back 29

1. Acidic. The acidic protons protonate the carbonyl oxygen twice to form water as a leaving group.
2. Imine
3. A hydrogen from alpha carbon jumps to the nitrogen, forming an enamine.

Front 30

Nitriles
1. What is it
2. If it is hydrolyzed in acid, it gives...
3. If it is reduced, it gives...

Back 30

1. C triple bond N
2. Carboxylic Acid
3. Amines

Front 31

Order of acidity for functional groups from weakest to strongest

Back 31

1. Alkane
2. Alkene
3. H2
4. NH3
5. Alkyne
6. Aldehyde/Ketone
7. Alcohol
8. water
9. carboxylic acid

Front 32

When fatty acids are oxidized, what is produced?

Back 32

1 NADH
1 FADH2
1 Turn of krebs cycle

Front 33

One turn of krebs cycle yields:

Back 33

3 NADH
1 FADH
1 GTP

Front 34

Isoelectric point:
1. What is pI?
2. What is the charge on an amino acid when the pH is less than its pI?
3. What is the charge on an amino acid when the pH is more than its pI?

Back 34

1. The pH at which the amino acid is a zwitterion, or has a + and - charge
2. It has a net positive charge. The acidic environment keeps all groups protonated.
3. It has a net negative charge. The basic environment deprotonates all groups.

Front 35

What kind of anomer is glucose if hydroxyl group on highest numbered chiral carbon is the left?


...is to the right?

Back 35

L anomer

D anomer

UPPERCASE LETTERS!
Nothing to do with observed rotation.

Front 36

NMR
1. What must the atomic number be?
2. What does this number do?
3. What does a NMR machine do?
4. When is resonance observed?
5. What is the calibration chemical?

Back 36

1. odd
2. creates a magnetic field around the nucleus
3. applies a variable external magnetic field, with a photon source that has a constant frequency
4. When photon has frequency that matches energy difference between low energy and high energy spin states.
5. TMS - tetramethylsilate

Front 37

How does C13 NMR relate to proton NMR?

Back 37

The same thing, except no signal splitting is observed.

Front 38

The higher the Rf factor...

Back 38

The more the substance travels with the mobile phase.

ratio of component over solvent front

Front 39

Distillation
1. Separates mixtures on basis of
2. What is the boiling point of a mixture?
3. What can make number two wrong?

Back 39

1. boiling point
2. the boiling point of the compound with the lowest boiling point
3. if the mixture is an azeotrope, or a mixture with a boiling point other than the boiling point of the compound with the lowest boiling point

Front 40

Extraction
1. What two layers are initially present
2. What group is extracted first and how
3. what group is extracted next and how
4. what group is extracted next and how

Back 40

1. Aqueous and organic
2. The bases are extracted first by adding acid, shaking vigorously, protonating the bases, and extracting the aqueous
3. strong acids are taken next, by adding weak bases, which deprotonates the strong acids, adds them to the aqueous layer, and then they are extracted
4. weak acids are removed by adding strong bases. same as above.

Front 41

Resonance structures:
What are they, really?

Is a resonance structure ever really a true molecule?

Back 41

They are structures that collectively resemble what the molecule really is. They are used in cases of electron delocalization.

NO. It is just something that describes partly what the molecule is.

Front 42

EAS:
Halogenation
1. Adding what to an aromatic ring?
2. What is the catalyst?

Back 42

1. Br or Cl
2. Lewis Acid, like FeCl3, FeBr3, AlBr3, or AlCl3, and heat

Front 43

EAS:
Sulfonation
1. Adding what to an aromatic ring?
2. Reaction ingredients

Back 43

1. Sulfonic Acid
2. SO3 / H2SO4

Front 44

EAS:
Nitration
1. Adding what to an aromatic ring?
2. Reaction ingredients
3. What does this combination of ingredients do?
4. What is the final product?

Back 44

1. Nitro group
2. H2SO4 / HNO3
3. Produces nitro group, a really good electrophile
4. An aromatic nitro compound, the least reactive aromatic compound

Front 45

EAS:
Acylation (Friedel-Crafts Reactions)
1. Adding what to an aromatic ring?
2. What are the reaction ingredients?

Back 45

1. An acyl group
2. AlCl3 (any lewis acid) creates a fine electrophile of the acyl group

Front 46

Catalytic Reduction of Benzene:
1. What happens?
2. What are the reaction conditions?

Back 46

1. The benzene ring loses all its double bonds to become cyclohexane.
2. H2, Rh/C, 100 degrees celcius

Front 47

What happens when you reduce an ester?

Back 47

Two alcohols are formed.

LiAlH4 can do this

Front 48

Reducing agents and what they do
1. LiAlH4
2. NaBH4

Back 48

1. Strong reducing agent - converts carboxylic acids, esters, aldehydes, ketones into corresponding alcohols. Converts Amide, Nitro, Azine compounds into amines.

2. Mild reducing agent. Reduces ketones and aldehydes to alcohols. Will not reduce carboxylic acids, esters, or amides.

Front 49

Oxidizing agents and what they do
1. Tollens reagent

Back 49

1. Ag(NH3)2, used to test for aldehydes. Will oxidize aldehydes to carboxylic acids.