Organic Chem - Test

Alkanes/Base formula?

Single bond, CnH(2n+2)

Alkene/Base formula?

Double bond (C=C), CnH(2n)

Alkyne/Base formula?

Triple bond, CnH(n-2)

Stereoisomers/Which group on top/bottom?

Cis- both hydrogen or lower priority on bottom

Trans - adjacent

Aromatic Hydrocarbons

Formula: C6H6

Groups attached/parent - Benzene

Substituent - Phenyl

One methyl - Toluene

example: Chlorobenzene, bromo benzene

Ortho (1,2), Meta (1,3), Para (1,4)

1,2 - dimethyl benzene — orthoxylene (alt. Naming)

Properties:

Generally nonpolar.

Insoluble in water.

Soluble in nonpolar solvents.

Combustible.

Benzene is toxic

Reaction: Undergo substitution under extreme conditions (alkylation, halogenation, nitration) replace an H w/ alkyl, halogen, nitrate (NO2)

Alcohol

Functional group - Hydroxyl (-OH)

Suffix (-ol), when not priorjty (hydroxy)

Choose longest chain with (OH)

Primary - attached to 1 R group, secondary - attached to 2 R group, tertiary, attached to 3 R groups

Properties:

Polar because of –OH.

Can form hydrogen bonds.

Higher boiling points than comparable alkanes.

Short-chain alcohols are water-soluble.

Solubility decreases as carbon chain length increases

Ethers

Functional group : R-O-R¹

Oxygen connects two groups

alkOXYalkane

(Side with longer chain is -ane)

E.g., methoxyethane

Properties:

Slightly polar due to C–O bonds.

Can accept hydrogen bonds but cannot hydrogen bond with themselves.

Lower boiling points than comparable alcohols.

Small ethers have some water solubility.

Aldehydes

Contains a (C=O) carbonyl group

Always on Carbon #1

Suffix -ol

Properties:

Polar due to C=O.

Can accept hydrogen bonds but cannot hydrogen bond with themselves.

Lower boiling points than comparable alcohols.

Small aldehydes are water-soluble

Ketones

Contains (C=O) carbonyl group

Gen. R-CO-R¹

Always within carbon chain

Example: propanone (acetone)

Give lowest possible number

Properties:

Polar due to C=O.

Can accept hydrogen bonds but cannot hydrogen bond with themselves.

Higher boiling points than comparable alkanes.

Lower boiling points than comparable alcohols.

Small ketones are water-soluble.

Carboxylic Acid

Contains (COOH) carboxyl group

Has C=O and OH

Suffix (oic acid)

Always in #1 carbon

Could have multiple COOH group, dioic (keep -e)

E.g., ethanoic acid

Properties:

Polar.

Can form hydrogen bonds.

High boiling points.

Weak acids (partially ionize in water).

Small carboxylic acids are water-soluble.

Esters

Gen structure: R - COO - R¹

(Oxygen in the middle, double bond O on one side, alkyl group on other side)

Carboxylic acid + alcohol —> esterification

alkYLalkylOATE

-yl from alcohol

-oate from carboxylic acid

E.g., ethyl ethanoate

(Side with double bond O is the -oate side)

Properties:

Polar.

Cannot hydrogen bond with themselves.

Lower boiling points than comparable carboxylic acids.

Often have fruity smells.

Small esters have some water solubility.

Amines

Derived from ammonia, NH2

Suffix - amine

When it is not the priority, use prefix amino

Primary, when it has 1 alkyl group, secondary, 2 alkyl group, tertiary, 3 alkyl groups

Properties: Polar.

Primary and secondary amines can hydrogen bond with each other.

Tertiary amines cannot hydrogen bond with themselves.

Generally weak bases (accept H⁺).

Small amines are water-soluble.

Amides

Functional group: CONH2

Contains carbonyl DIFFERENCE FROM AMINE : (C=O) directly on nitrogen

-amide suffix

-Use N- as prefix to say alkyl group attached to Nitrogen

E.g., N-ethyl-N-methylbutanamide

Butanamide = 4-carbon parent chain including the carbonyl carbon.

N-methyl = CH₃ branch on Nitrogren

N-ethyl = ethyl group attached directly to nitrogen.

The carbonyl carbon is always carbon 1.

Formed from - carboxylic acid + alcohol

Properties

Polar.

Primary and secondary amides can hydrogen bond.

High boiling points due to hydrogen bonding.

Small amides are generally water-soluble.

Generally neutral (not basic like amines).

Alkyl halides