13. (More!) Organic Families

not -CHO bad!

tetrahedral geometry

4 single bonds

planar geometry

double or triple bond

chloroalkane

a compound in which one or more of the hydrogen atoms in an alkane molecule have been replaced by chlorine atoms

to name a chloroalkane

draw compound, find parent alkane, number carbon chain, put number at start of name

chloroalkane intramolecular bonds

polar covalent (C-Cl), non polar covalent (C-H)

chloroalkane intermolecular forces

van der waals (C-H), dipole-dipole (C-Cl)

chloroalkane boiling point

higher than corresponsing alkanes due to polarity of C-Cl bond, still low

chloroalkane solubility

soluble in cyclohexane, slightly soluble in water

chloroalkane uses

dry cleaning clothes, solvent for removing oil and grease

alcohol functional group

-OH (hydroxyl group)

alcohol functional group mnemonic

-OH! i would love a gin and tonic!

to name an alcohol

draw compound, name parent alkane, change e to ol, number carbon chain, put number in middle of name

primary alcohol

an alcohol that has one carbon atom attached to the carbon directly attached to the OH group

secondary alcohol

an alcohol that has two carbon atoms attached to the carbon directly attached to the OH group

tertiary alcohol

an alcohol that has three carbon atoms attached to the carbon directly attached to the OH group

alcohol intramolecular bonds

polar covalent (O-H), non polar covalent (C-H)

alcohol intermolecular forces

hydrogen bonding, van der waals

alcohol boiling point

higher than alkanes due to hydrogen bonding

alcohol solubility

soluble in cyclohexane, smaller carbon chains soluble in water

alcohol uses

ethanol in alcoholic drinks and in fuels as an oxygenate, methanol in industrial alcohol as a denaturing agent

carbonyl group

C=O

organic families containing carbonyl group

aldehyde, ketone, carboxylic acid, ester

aldehyde functional group

CHO

to name an aldehyde

draw compound, name parent alkane, change e to al, number carbon chain, put number in front of name

aldehyde intramolecular bonds

polar covalent (C=O), non polar covalent (C-H)

aldehyde intermolecular forces

dipole-dipole, van der waals

aldehyde boiling point

higher than alkanes/alkenes/alkynes, lower than alcohols

aldehyde solubility

soluble in cyclohexane, smaller carbon chains soluble in water

aromatic aldehydes

aldehydes containing a benzene ring

aromatic aldehyde example

benzaldehyde

aldehyde uses

bezaldehyde as almond extract in cooking

ketone functional group

C-C(=O)-C

ketone functional group mnemonic

looks like a KEY(tone)

need to know ketones

propanone, butanone

ketone intramolecular bonds

polar covalent (C=O), non polar covalent (C-H)

ketone intermolecular forces

dipole-dipole, van der waals

ketone boiling point

higher than alkanes/alkenes/alkynes and aldehydes, lower than alcohols

ketone solubility

soluble in cyclohexane, smaller carbon chains soluble in water

ketone uses

propanone (acetone) used as a solvent/nail polish remover

carboxylic acid functional group

COOH (carboxyl group)

to name a carboxylic acid

draw compound, name parent alkane, change e to oic acid, number carbon chain, put number at start of name

carboxylic acid intramolecular bonds

polar covalent (C=O, C-O, O-H), non polar covalent (C-H)

carboxylic acid intermolecular forces

2 hydrogen bonds can form dimers, van der waals

carboxylic acid boiling point

highest due to dimers

carboxylic acid solubility

soluble in cyclohexane, smaller carbon chains soluble in water

carboxylic acid uses

ethanoic acid in vinegar, propanoic acid and benzoic acid used as food preservatives

aromatic carboxylic acid example

benzoic acid

esters functional group

R-C(=O)-R'

esters functional group mnemonic

esteR, Rest of molecule

esterification

the reaction between an alcohol and a carboxylic acid to form an ester

esterification can also be called…

substitution reaction

substitution reaction

a chemical reaction in which an atom or group of atoms in a molecule is replaced by another atom or group of atoms

esterification formula

alcohol + carboxylic acid = ester + water

to name an ester

identify alcohol and carboxylic acid parts, write name of alkyl group from alcohol, replace oic acid with oate, put alkyl group first in name

ester intramolecular bonds

polar covalent (C=O, C-O), non polar covalent (C-H)

ester intermolecular forces

dipole-dipole, van der waals

ester boiling point

higher than alkanes/alkenes/alkynes, similar to but lower than aldehydes and ketones, lower than carboxylic acid and alcohol

ester solubility

soluble in cyclohexane, smaller carbon chains soluble in water

ester uses

perfume due to floral and fruity scent, polyester used in clothing, ethyl ethanoate used as a solvent in cleaning and paint removal

aromatic hydrocarbons contain…

a benzene ring

need to know aromatic hydrocarbons

methylbenzene used as an industrial solvent

aromatic pharmaceutical compound

aspirin

aromatic acid-base indicator

phenolphthalein and methyl orange

carinogenic aromatic compound

benzene

homologous series boiling points highest to lowest

carboxylic acids, alcohols, ketones, aldehydes, esters, alkanes/alkenes/alkynes