Chem II - Topic 1 and 2 (organic chem)

Aldehyde structure:

Carbon is bonded to one Hydrogen, double bonded to one Oxygen and is connected to one other chain

Ketone structure:

Carbon is double bonded to one Oxygen and has two chains.

Carboxylic Acid structure:

Carbon is double bonded to one Oxygen, bonded to one OH and bonded to a chain.

Ester structure:

C double bonded to one Oxygen, single bonded to one Oxygen, bonded to a chain.

Acyl chloride structure

Carbon bonded with Cl and has one double bond with oxygen.

Alkyl chloride structure

A chain bonded with one Cl molecule.

(R-Cl)

Phenol structure

OH bonded to a benzene ring.

Benzoic Acid structure

Benzene ring bonded to COOH.

Aniline Structure

Benzene ring bonded with NH2.

Toluene structure

Benzene ring bonded with CH3/methyl

What functional group are ‘anol’ and ‘ol’ used for?

Alcohol

What functional group are ‘anal’ and ‘al’ used for?

Aldehyde

What functional group are ‘anone’ and ‘one’ used for?

Ketone

What functional group are ‘anamine’ used for?

Amines

What functional group are ‘anoyl chloride’ used for?

Acyl Chloride

What is the general formula for open chain alkanes?

Cn H2n+2

What is the general formula for closed chain alkanes and open chain alkenes?

Cn H2n

What is the general formula for alcohols and esters?

Cn H 2n+2 O

What is the general formula for halogenated aromatic compounds?

Cn Hn-2 X2

What is a carbonyl?

Group consisting of Aldehydes and Ketones

What is the general formula for open chain carbonyl compounds?

Cn H2n O

What is the general formula for carboxylic acids and esters?

Cn H2 O2

What functional groups are insoluble?

Alkanes. Alkenes, Alkynes, and Benzene (All are non-polar)

What functional groups are soluble?

Aldehydes and Ketones (Polar)

What functional groups are very soluble?

Alcohols (OH in alcohol has strong interactions with water molecules)

What functional groups are the most soluble?

Carboxylic acids (OH in carboxylic acids has VERY strong interactions with water molecules)

What affects solubility?

The higher the molecular mass, the lower the solubility.

‘Like dissolves-’ what

‘like dissolves like’

Polar molecules dissolve in polar solvents

Non polar molecules dissolve in non polar solvents

Which functional groups have the lowest boiling points?

Alkanes, alkenes (Typically dispersion forces)

Which functional groups have the second lowest boiling points?

Ethers, aldehydes, ketones, esters, tertiary amines (Dipole-dipole forces and dispersion forces)

List down amines with the lowest boiling point to the highest boiling point.

Tertiary amines, secondary amines, primary amines

Which functional groups have the highest boiling points?

Amides with H bonded to N

What affects boiling points in the same functional group?

The larger the molecular mass, the higher the boiling point as there are more intermolecular forces.

How does branching affect the boiling point?

More branching results in less surface area, which leads to lesser intermolecular forces of attraction. This causes a lower boiling point.

Complete combustion:

When an organic compounds burn in excess O2 to give CO2 and H2O

Addition:

When a small molecule is added to an organic compound

Elimination:

When a small molecule is removed from an organic compound

Substitution:

When an atom/group is replaced with another atom/group

Condensation:

Two organic compounds combining to form a larger product and a smaller side product

Hydrolysis:

An organic compound is broken apart using H2O

Oxidation:

Carbon in an organic compound forms additional bonds with O

Reduction:

Carbon in an organic compound forms more bonds with H

Catalyst for addition

H+/Platinum

Catalyst for addition with chlorine/bromine

Br/CCL4

Cl/CCl4

Bromination (Chemical test)

Tests for the presence of C=C bonds

A brown solution that decolorizes in the presence of C=C

*Benzene doesn’t react with bromine

Markonikov’s rule

Hydrogen will be added to molecule with more hydrogen atoms during reactions like hydration

Catalysts for hydration:

H20/H+

Gentle oxidation

-Takes place where there is double bonds

→only one of the bonds in the double bond breaks

-Uses cold, dilute alkaline KMnO4

-A chemical test for presence of unsaturated bonds

→Purple to colourless, brown ppt forms

Harsh oxidation

-Takes place where there is double bonds

→Breaks the molecule at double bond and forms multiple products

-Uses hot, acidic KMnO4

-one O atom bonds with electrophilic carbon, and to H attached to electrophilic carbon

Can benzene go through addition?

No. The rotating C=C bonds make it difficult to isolate, and therefore stable

Can benzene go through substitution?

Yes

Catalyst for substitution with halogens in aromatic compounds:

Cl2/FeCl2

Br2/FeBr2

Catalyst for nitration in aromatic compounds:

Concentrated HNO3/Concentrated H2SO4

Catalyst for substitution with alkyl chloride in aromatic compounds:

RCl/ACl3

With Friedal Craft’s Alkylation

Catalyst for oxidation of alkyl benzene:

hot H+/KMnO4

Which kind of butylbenzene cannot undergo oxidation?

Tertiary butylbenzene

What is the catalyst for alcohol/ester substitution?

PCl3

PCl5

SOCl2

Steps of oxidation of alcohol to carboxylic acids:

Reagents:

H+/KMnO4

H+/K2Cr2O7

H+/Na2Cr2O7

Step 1:

Remove 2 hydrogen atoms, one from OH and one from electrophilic carbon.

Step 2:

Convert C-O to C=O

Step 3:

If electrophilic carbon has H atom attached to it, add O to that H atom

Steps of reduction of carboxylic acid to alcohol:

Reagents:

LiAlH4/ether and H+/H2O (both are in one set)

Step 1:

If electrophilic carbon has OH attached to it, remove O

Step 2:

Concert C=O to C-O

Step 3:

Add 2 H atoms, one to the O and one to the electrophilic carbon

Dehydration reagent:

Concentrated H2SO4

Reagents of oxidation of Aldehydes to carboxylic acid

Acidic KMnO4 → turns from purple to colorless

Na2Cr2O7 → Turns form orange to green

K2Cr2O7 → Turns form orange to green

Step 1:

Add O to the hydrogens connected to the electrophilic C

Reagents of reduction of Aldehydes to alcohol

H2/Platinum

LiAlH4/ether + H+/H2O

Steps of reduction of Aldehydes to alcohol

Step 1:

C=O to C-O

Step 2:

Add H to O and electrophilic C

Reduction of ketones:

Reagents:

H2/Platinum

LiAlH4/ether + H+/H2O

Step:

Add hydrogen to O and electrophilic carbon

Tollen’s test

-uses [Ag(NH3)2]

-When aldehydes are preset, silver mirror forms

Fehling’s test

-Uses Fehling’s solution

-When aldehydes are present, brick red ppt forms

2-4 - DNPH test

-Uses 2, 4 - dinitrophenylhydrazine

-Forms red/yellow/red ppt in presence of carbonyl compounds

Iodoform test

-Uses NaOI

-tests for presence of CH3 bonded with electrophilic carbon

Acidic compounds in organic chem

Carboxylic acid > Phenol > Alcohol

Acidic things that react with metal

Carboxylic acid, phenol, alcohol

All give salt +H2

Acidic things that react with strong bases

Carboxylic acid and phenol

Both give salt and H2O

Acidic things that react with weak bases

Carboxylic acid

Gives salt and H2O

How to name esters:

Step 1

Look for C=O, then O-C from electrophilic carbon

Step 2

Highlight carboxylic acid (Part with no O-C)

Other side is alcohol

Step 3

Put alcohol part first, then acid

Reagent for esterification:

H⁺

Reagent for hydrolysis of acyl chloride:

H2O

Reagent for acid hydrolysis of esters:

H+/H2O

Reagent for base hydrolysis of esters:

NaOH (aq)

Reagent for neutralization of amine

HCl