test 2

Aldehyde

-al

Ketone

-one

Carbonyl group

Pentanal

Aldehyde

2-pentanone

3-pentanone

Structural isomer, middle carbon splits

2-methylcyclopentanone

3-methylcyclohexanone

Benzene

Toluene

Phenol

Benzaldehyde

Parent; cyclopenanone

Cloro and methyl

3-Cloro-2-methylcyclopentanone

Functional group: alcohol

2-methylcyclopentanol

Oxidation: aldehydes

Form carboxylic acid.

Ethanol to ethanoic acid

-H → [o] → -OH

Ketones : oxidation

Does nothing, no reaction

-CH3 →[o]→ N.R.

Tollens’ test

Distinguish between aldehydes and ketones, used for aldehydes

Uses Ag+ (silver)

Silver ion reduced and forms silver mirror

Benedict’s test

Aldehyde test

Cu2+ added to aldehyde and heated, brick red solid of Cu2O forms

Negative for ketones

Can be used to determine presence of glucose in blood or urine

Benedict’s test

Aldehyde test

Cu2+ added to aldehyde and heated, brick red solid of Cu2O forms

Negative for ketones

Can be used to determine presence of glucose in blood or urine

Benedict

Reduction: general

Aldehydes and ketones are reduced hydrogen using catalyst like nickel (Ni), platinum (Pt) or palladium

Reduction of aldehyde or ketones…

There is decrease in number of carbon oxygen bonds

Aldehydes reduce to…

Primary alcohols

Ketones reduce to….

Secondary alcohols

Aldehyde reduction

Primary alcohol

OH

R-C-H

H

Primary alcohols have

H on terminal end

Ketone reduction

Secondary alcohol

Seoncdary alcohols have what

R (CH3) on terminal end

OH

CH3-C-CH3

H

Hemiacetal formation : general

When one alcohol adds to the carbonyl group of aldehyde or ketones

Hemiacetals contain what two functional groups

Hydroxyl (-OH)

Alkoxy group (-OR)

ARE BONDED TO SAME C ATOM

General equation for the formation of a hemiacetal

Examples of formation of hemiacetal, aldehyde

Example of formation of hemiacetal, ketone

Acetal formation: general

Acetal forms when 2 alcohols add to carbonyl group of aldehyde or ketones in presence of acid catalyst

Acetal contains what

2 alkoxy groups (-OR) attached to initial carbonyl carbon atom

General equation for the formation of an acetal

Acetals also have what at the end product, but typically not written?

H2O

Carbonyl group

Aldehyde

Ketone

Carboxylic group

Ester

Naming carboxylic acids (-OH)

Drop e and add -oic acid

Naming carboxylic acid: if there are substituents

The carbon chain is numbered beginning with the carboxyl carbon

Common names of carboxylic acids

Prefixes form, acet, propion, butyrate

Uses Greek prefixes for substituents alpha (a), beta (B), gamma (y)

Assigned to carbons adjacent to carboxyl carbon

Preparation of carboxylic acids

Carboxylic acids can be prepared from primary alcohols or aldehydes

Oxidation converts ethyl alcohol (primary) to acetaldehyde and then to acetic acid

Acidity

PH below 7 when dissolved in water

Neutralization

Reaction with a base makes salt and water

Basic pH

7-14

When carboxylic acid dissociates in water….

H+ is transferred to water mole

forms negatively charged carboxylate ion AND positively charged hydronium ion (H3O+)

Carboxylic acids are more…

Acidic than others, but are weak acids

Acids examples

CH3-OH

HO-H

HCL

O

CH3-C-OH

Adding H+ to acid examples.,.. they give up what

H+

CH3-O^-

HO^-

Cl^-

O

CH3-C-O^-

Carboxylic acids are completely neutralized by

Strong bases (NaOH and KOH)

Products of carboxylic acids

Carboxylate salt and water

Naming carboxylic acid neutralization products: carboxylate ion is named by

Replacing -ic acid ending with -ate

Neutralization of carboxylic acids

Neutralization

Neutralization

Swap Na for reactant H usually

When methanoic acid is neutralized w/ sodium hydroxide..

sodium methanoate Is product

When butanoic acid is neutralized W/ sodium hydroxide…

Sodium butanoate is product

Butanoic acid neutralized w/ potassium hydroxide…

Potassium butanoate

Benzoic acid neutralized w/ sodium hydroxide….

Sodium benzoate

Esterification: making an ester formula

Acid + alcohol → H+ → ester + h2o

How is ester made

—H of carboxylic acid is replaced by alkyl group

Carboxylic acid to ester

Esterification

Ester is produced when a carboxylic acid and an alcohol react in presence of an acid catalyst (H2SO4) and heat

Esterification process

The —OH group from carboxylic acid and the —H from alcohol are removed and combine to form water

Excess alcohol used to shift the equilibrium in the direction of the formation of ester product

Esterification example

Naming esters

First word indicates the alkyl part from alcohol

Second word is name of carboxylate from carboxylic acid

IUPAC names of esters

IUPAC names of acids

Reaction of esters: acid catalyzed hydrolysis for an ester forms

The acid and alcohol

Saponification

When ester undergoes hydrolysis w/ strong base (NaOH/KOH)

Amine

Nitrogen bonded to at least 1 carbon (one lone pair)

: CH3-OH

Methynal

CH3-OH-CH3

Ether

CH3-NH2

An amine

Naming amines: IUPAC

Drop e and add -amine

Naming amines ex: CH3-NH2

Methanamine

Naming amines ex; common name

Methylamine

R-NH3 / CH3-NH2

Primary amine

R2-NH / CH3-N-H

CH3

Secondary amine

R3-N

Tertiary amine