Organic Chemistry

When finding hybridization always remember about what

resonance structures which determine hybridization

sp hybridization has what geometry and bond angle

linear and 180

sp2 hybridization has what geometry and bond angle

trigonal planar, 120

sp3 hybridization has what geometry and bond angle

tetrahedral, 109.5

Oxygen exists normally with how many bonds and lone pairs

2 bonds and 2 lone pair

Nitrogen exists normally with how many bonds and lone pairs

3 bonds and 1 lone pair

Phosphorous exists normally with how many bonds and lone pairs

3 bonds and 1 lone pair

Sulfur exists normally with how many bonds and lone pairs

2 bonds and 2 lone pairs

MEMORIZE

What are Lewis Acids

compounds that serve as electron acceptors

What are Lewis Base

compounds that serve as electron donors

What is Bronsted Lowry Base

are proton (H) acceptors

What is Bronsted Lowry Acid

proton (H) donors

The lower the pKa, the _acid

stronger

What are the 7 strong acids

HClO3,

HBr,

HCl,

HI,

HNO3,

HClO4,

H2SO4

High Ka means

high Ka means strong acid. High Ka means lower pKa value

High pKa means

low Ka value. Also means weakest acid

What happens to acidity as we go down a column in the periodic table

Acidity increases because atomic size increases

In an acid-based reaction, what kind of acid is favored for production?

the formation of a weaker acid is favored

For an amino acid, what happens to the amino and carboxyl group depending on how high or low pH is

If the pH is higher than functional group’s pKa, then carboxyl group will be in base form (COO-) no Hydrogen. If pH is lower than pKa, carboxyl group will gain proton COOH. If pH is greater than pKa, amino group will be the same (NH2). If pH is less than pKa, amino group will gain proton NH3+

If atoms like Fluorine group are closer to carboxylic acid what does this mean in terms of how strong the molecule is

Groups like Fluorine when close to carboxylic acid, are electron withdrawing groups so they will stabilize the negative charge of the conjugate base of the chosen molecule, resulting in stronger acid.

Which ones are stronger acid one with carboxylic acid or only alcohol group

Carboxylic acid because the conjugate base of carboxylic acids are MORE STABLE

A bigger atom does what to acidity

increases acidity

Electron withdrawing groups like F, Cl, Br, I do what to acidity

increase

What are some electron withdrawing groups resulting in increasing acidity

From Greatest to smallest:

nitro (NO2), (SO3H), cyano (CN), carbonyls (CHO, C=O, COOH, COOR), halogens,

When determining which molecule is the most acidic: Use CARDIO

C → carboxylic acid is strongest acid

A → atom size the bigger the size of atom the more acidic

R → resonance! must be able to be resonance stabilized or do resonance (SO no cyclic rings without double bonds inside)

DI → dipole induction. Which groups are the most electron withdrawing?

O → lok at orbitals. sp most acidic, then sp2, and sp3 is least acidic

Strong conjugate base means..

weak acid (low Ka, high pKa)

weak conjugate base means

strong acid (High Ka, low pKa)

strong conjugate acid means…

weak base

weak conjugate acid means

strong base

What makes a molecule more basic in terms of what kind of functional group must be there and characteristics?

electron donating groups like NH2, NHR, N, OH, OR are strongest, then NHCO-, OCO-, lastly weakest is Ch3, CH2CH3

Hydrogen bonding can happen intermolecularly between what kinds of molecules? Fundamental atoms in there that can allow this

Hydrogen (H) bonded to Nitrogen (N), Oxygen (O), or Fluorine (F).

IUPAC naming rules

try to number the carbons as long as you can (largest number of carbon) to incorporate as much as you can.

the functional group is named alphabetically in order which determines the lowest number assigned

assign the lowest number to the functional groups

Alkyne

triple bond. when naming for IUPAC want to assign this lowest number as possible. Numbering should go through it

-yne

Alkene

double bond. Try to assign lowest number. Counting should go through this.

-ene

Name this

Bicyclo[1.1.0]butane

butane is parent name because there is 4 carbons

bicyclo in front of name

name this

spiro[3.4]octane 

count all the carbons around the shape

establish parent name.

then count how many carbons are on opposite side of the vertices that both share.

label in brackets from lowest value to highest for spiro ones!!!

dont forget to put spiro in front

Name this

Bicyclo[3.2.1]octane 

first name it bicyclo

then count how many total carbons and establish parent compound

then count how many carbons are NOT shared on either side separated by the bridge

then count how many carbons are shared in the bridge

label from descending value highest to lowest

name this

1-methylbicyclo[4.4.0]decane

How do you name a molecule with functional group like this

We use “N,N-dimethyl” to indicate that there are two methyl groups bonded to the amide nitrogen.

Where should you place carbon 1 on this molecule

On the carbonyl.

what functional group has the highest priority when the parent name ends in “-oic acid”

carboxylic acid

ester

for esters IUPAC naming as the parent chain what do you attach

-oate

make sure that you also attach the name of the functional group bonded after the oxygen in the ester functional group in front of the entire name

for instance for this problem the full name is Ethyl 3-methylbutanoate

HNMR how to know if the signal will be singlet, doublet, triplet, quartet

n + 1 rule where n is the # of neighboring H’s around the designated proton and final answer will see if it is either one of those. The neighboring H must be from outside the carbon atom orignally attached to

Which compound will produce a large broad peak at 3200-3500 cm^-1 on IR spectrum

Alcohol group (-OH)

On an IR spectrum what are the characteristics of an Amine group (NH)

There will be a sharp peak at 3200-3500 cm^-1 and a secondary amine (-NR2H) peak and 2 primary amine peaks (-NRH2)

On an IR spectrum what are the characteristics of an Carboxylic acid group (-COOH)

2500-3500 cm^-1 and has broad jagged peak

On an IR spectrum what are the characteristics of an Nitrile group (-COOH)

2200-2250 cm^-1 and medium peak

On an IR spectrum what are the characteristics of an carbonyl group (C=O)

1700-1750 cm^-1 large sharp peak

On an IR spectrum what are the characteristics of an aromatic group

1450-1600 cm^-1 medium peak

Ethanol

Ethanal

Ester