MCAT OChem

Double bond

Alkene

Triple bond

alkyne

Name for alcohol

hydroxyl group

Ending for alcohol

-ol

Having two alcohol groups

diol/ glycols

Two alcohols on the same carbon

geminal diol

Two alcohols on different carbons

vicinal diols

Ending for aldehyde

-al

Ending for ketone

-one

Common name and IUPAC name

formaldehyde and mathanal

Common name and IUPAC

acetaldehyde and ethanal

Common name and IUPAC

Propionaldehyde and propanal

Ketone ending

-one

Common name and IUPAC

propanone and acetone

Common name and IUPAC

Formic acid and methanoic acid

Common name and IUPAC

acetic acid and ethanoic acid

Common name and IUPAC

Propanoic acid

Constitutional isomers

Having the same molecular formula and weight

Confrontational isomers

The same molecule but a sigma bond is different

Gauche

The largest two groupd are 60 degrees apart (staggered)

Totally eclipsed

highest energy state the two methyl groups overlap

Torsional Strain

Cyclic molecule. Gauche and eclipsed interactions

Non-bonded strain and van der waals interactions

non-adjacent atoms and groups compete for the same place! (The molecule will try to pucker and change shape to combat this)

What position do bulky groups prefer?

Equatorial

Configuration isomer

Need to break a bond to change

Diastereomere

Not a mirror image. Superimposable

Chiral

Non-superimposable mirror image. NO internal plan of symmetry. Enantiomers

Achiral

Superimposable mirror images.

Enantiomers

Non-superimposable mirror images

Optically Active

Rotate plane-polarized light chiral molecule

Racemic mixture

Both + and - in equal concentration cancel each other out with no optic activity

Diastereomers and enantiomer magnetude

E = having an equal magnitude rotation in opposite direction. Diastereomers will be different

Meso

Molecule has chiral centers and a plane of symmetry that is internal. NOT optically active

Sigma bonds

head to head overlap or tail to tail

Pie bonds

side by side overlap. W/ node in the middle

Lewis Acid

Electron acceptor. Electrophile

Lewis base

Electron donor. Nucleophile

Acidic molecules pka

small

Basic molecules pka

large

Proton

In nucleus. Half of the atomic weight

Neutrons

No charge. The other half of the element’s mass

Electrons

moving through the space around the nucleus. Negative charge

Atomic mass

Sum of the protons and electrons

Atomic weight

What is listed on the periodic table. Average of the isotopes

Nucleophiles

Has lone pairs and pie bonds. Forms bonds to electrophiles. Negative charge

Polar protic

Nucleo increases going down the table. HAS hydrogen bonds

Polar Aprotic

Nucleo increases going up the table. Does NOT have hydrogen bonds

Strong Nucleophiles

HO-, RO-, CN-, N-3

Fair Nucleophiles

NH3, RCO2-

Weak Nucleophiles

H20, ROH, RCOOH

Electrophiles

Electron loving. Positive charge. Accepts the electron pair when forming new bonds.

Leaving Groups

Weak bases are good leaving groups. Effected by resonance and inductive effects.

SN2 will experience

An inversion and backside attack

Chemoselectivity

Preferential reaction of one functional group

Oxidation

Increase in oxidation sate. Loss of electrons. Increasing the number of bonds to oxygen or the heteroatom

Reduction

Decrease in oxidative state. Gain in electrons. Increasing the number of bonds to hydrogen

Oxidizing agent

Accepts electrons from another species. Reduces itself. Often metals with large number of oxygen atoms.

Reactivity of functional groups

Anhydrides → Carboxylic acid and esters → amides

the common names for alcohols

Adding alcohol to the alkyl group name

Phenols

Alcohols attached 2 aromatic rings

What is this structure

phenol

Sub location

Ortho

Sub location

Meta

Sub location

Para

Why do alcohols have higher boiling points?

They are capable of intermolecular bonding

PCC oxidizes primary alcohols into…

aldehydes

PCC oxidizes secondary alcohols into…

ketones

Jones oxidation

CrO3. Primary to carboxylic acid. Secondary to ketone.

Mesylate or tosylate

Makes the leaving group better!!!! Is a protecting group

Acetal/ Ketal

Are protecting groups involving OH

What is this structure

Quinone

What is this structure

Phylloquinone

Carbonyl

Double bond between teh carbon and oxygen. CAN act as nucleophile or electrophile. Common. IN carboxylic acids/ esters/ amides/ anhydrides and others

Aldehydes/ Ketone

Volatile. Strong smelling.

Carbaldehyde

When an aldehyde is attached to ring

Oxo

When aldehydes and ketones act as substituents

Common and IUPAC name

Butanal and Butyraldehyde

Common and IUPAC

Pentanal and Valeraldehyde

Common name for Ketones

Name the alkyl groups A - Z then use “Ketone”

Naming ketone as a substituent

Prefix = keto- and oxo-

Why are aldehydes more reactive to nucleophiles than ketones

Because of steric hinderance

Aldehydes and ketones will act as

an electrophile

How to form an Aldehyde

PCC and a primary alcohol

How to form a ketone

secondary alcohol and PCC. Chromium trioxide (CrO3). Sodium dichromate salt (Na2Cr2O7). Potassium dichromate salts (K2Cr2O7).

What is this structure

Hemiacetal/ hemiketal

What is this structure

Actal

What is this structure

Ketal

Imine

NU. nitrogen with a double bond to the carbon.

Tuatomerization of an imine creates

emamine

Hydride Reagents

Reduction to make alcohols. Lithium aluminum hydride (LiAlH4). Sodium borohydride (NaBH4).

Enol

Carbon carbon double bond

Tautomers

the two isomers

Tautomer equalibrium

keto sided. Called tautomerization or enolization

α racemization

rapid conversion between keto/ enol

What is this structure?

Enol

Kinetically controlled product of tautomerization

rapid and not as stable. Double bond is to less substituted α-carbon.

Thermodynamically controlled product

Slower and more stable. Double bond is to the more substituted α-carbon.

What is this structure

Imine

What is this structure

enamine