organic

molecules :) * acyl chlorides

general formula: [R]COCl

suffix: ~oyl chloride * what are acyl chlorides made out of?

acyl chlorides consist of a double bond of carbon to an oxygen atom at the edge of the molecule, this carbon atom is also bonded to a chlorine atom * what reactions can acyl chlorides undergo? * substitution reactions * substitution to amides

Reagent: conc NH3 (alcoholic) * substitution/hydrolysis to carboxylic acids

Reagent: H2O * how are acyl chlorides formed?

acyl chlorides can be formed in substitution reactions from carboxylic acids using the reagent thinoyl chloride - SOCl2 * alcohols

general formula: [R]OH

suffix: ~ol * what are alcohols made out of?

carbon molecules bonded to an OH molecule * what reactions can alcohols undergo? * elimination reactions * elimination/dehydration/condensation to alkenes

Reagent: concentrated H2SO4 * substitution reactions * substitution to haloalkanes

Reagent: concentrated HCl or SOCL2 * substitution/esterification/condensation to esters

Reagent: carboxylic acid + concentrated H2SO4 * oxidation reactions * total oxidation to carboxylic acids

Reagent: MnO4-/H+ or Cr2O72-/H+

Conditions: reflux * 1° partial oxidation to aldehydes

Reagent: MnO4-/H+ or Cr2O72-/H+

Conditions: warm gently and distill

Observations: orange Cr2O72- reduces to green Cr3+ ion

or purple MnO4- reduces to colourless Mn2+ ions * 1° full oxidation to carboxylic acids

Reagent: Cr2O72-

Conditions: heat under reflux * 2° oxidation to ketones

Reagent: KMnO4/H+ or K2Cr2O7/H+ * how are alcohols formed? * addition/hydrogenation from alkenes

Reagent: dilute H2SO4 * substitution from haloalkanes

Reagent: KOH (aqueous) or NaOH (aqueous) * substitution/acid or base hydrolysis from esters

Reagent: H2O

A hydrolysis reaction uses water to split a large organic molecule into smaller organic molecules. The C=O gains –OH from water, and the C–O gains –H from water. Both acidic and basic hydrolysis require heat under reflux. Acidic hydrolysis requires a dilute acid (e.g. dil. H2SO4), whereas basic hydrolysis requires a dilute base (e.g. dil. NaOH). * reduction from aldehydes and ketones

Reagent: NaBH4 * aldehydes

general formula: [R] CHO

suffix: ~al * what are aldehydes made out of?

aldehydes consist of a carbon double bonded to an oxygen atom at the edge of a molecule, this carbon atom is also bonded to a hydrogen atom.

they are more reactive then ketones * what reactions can aldehydes undergo? * oxidation to carboxylic acids

Reagent: MnO4-/H+ or Cr2O72-/H+ or tollens (Ag+) or Fehlings (Cu2+) or benedicts (Cu2+) * reduction to alcohols

Reagent: NaBH4 * how are aldehydes formed? * partial oxidation from 1° alcohols

Reagent: MnO4-/H+ or Cr2O72-/H+ and distillation * alkenes

general formula: CnH2n

suffix: ~ene * what are alkenes made out of?

alkenes are unsaturated hydrocarbons that primarily consist of hydrogen and carbon and contain a double carbon bond * what reactions can alkenes undergo? * oxidation to diols * what conditions are required?

Reagent: MnO4-/H+ * how are they formed?

many small monomer unsaturated alkenes bond together to form a long polymer chain * addition reactions * addition/hydrogenation to alcohols * what conditions are required?

Reagent: dilute H2SO4

Catalyst: nickel/platinum * addition/hydrogenation/bromination/chlorination to haloalkanes * what conditions are required?

Reagent: HBr, HCl, Br2 * symmetrical vs asymmetrical alkene addition

when undergoing addition reactions, the hydrogen atom will bond to the carbon already bonded to the highest number of hydrogen atoms - the rich get richer - to create a major product. if this does not occur, a minor product is formed. * how are alkenes formed? * elimination reactions * elimination from haloalkanes * what conditions are required?

Reagent: KOH (alcoholic) * elimination/dehydration/condensation from alcohols * what conditions are required?

Reagent: concentrated H2SO4 * alkynes

general formula: CnH2n-2

suffix: ~yne * amides

general formula: [R]CONH2

suffix: ~amide * what are amides made out of?

amides consist of a carbon double bonded to oxygen at the edge of the molecule, this carbon is also bonded to an NH2 ammonia group * what reactions can amides undergo? * how are amides formed? * substitution reactions * substitution from carboxylic acids

Reagent: NH3 and heat * substitution from acyl chlorides

Reagent: concentrated NH3 (alcoholic) * from esters * amines

general formula: [R]NH2

suffix: amine * what are amines made out of?

a carbon chain bonded to a NH2 ammonia molecule

they have higher boiling points then alkanes, but lower than alcohols * how are amines formed?

amines can be formed though substitution reactions from haloalkanes. these reactions need the reagent of concentrated NH3 (alcoholic) to occur * carboxylic acids

general formula: [R]COOH

suffix: ~oic acid * what are carboxylic acids made out of?

carboxylic acids consist of a carbon double bonded to oxygen at the edge of the molecule, this carbon atom is also bonded to an OH hydroxide molecule * what reactions can carboxylic acids undergo? * substitution to acyl chlorides

Reagent: SOCl2 * substitution to amides

Reagent: NH3 and heat * substitution/esterification/condensation to esters

Reagent: alcohols and H2SO4 * how are carboxylic acids formed? * substitution reactions * substitution/hydrolysis from acyl chlorides

Reagent: H2O * oxidation reactions * total oxidation from alcohols

Reagent: MnO4-/H+ or Cr2O72-/H+ or tollens (Ag+) or Fehlings (Cu2+) or benedicts (Cu2+) * oxidation from ketones

Reagent: MnO4-/H+ or Cr2O72-/H+ under reflux * diols * how are diols formed?

oxidation from alkenes, with reagent MnO4-/H+ * esters

general formula: [R]COO[R]

suffix: yl/oate * what are esters made out of?

esters consist of a carbon double bonded to an oxygen molecule in the molecule, this carbon is also bonded to another oxygen atom * what reactions can esters undergo?

esters can undergo reactions with NH3 to form amides

or hydrolysis to form alcohols * how are esters formed?

esters are formed by substitution/esterification/condensation of alcohols and carboxylic acids with the reagent of concentrated H2SO4, the water molecule is removed, forcing the forward reaction * ketones

general formula: [R]CO[R]

suffix: ~one * what are ketones made out of?

ketones consist of a carbon atom double bonded to an oxygen atom at the centre of a molecule

they are less reactive than aldehydes * what reactions can ketones undergo?

ketones can undergo reduction reactions with the reagent NaBH4 to form alcohols * how are ketones formed?

ketones are formed by the oxidation of 2° alcohols with the reagent KMnO4-/H+ or K2Cr2O7/H+ * haloalkanes

general formula: [R][X]

suffix: ~ane * what are haloalkanes made out of?

a carbon chain bonded to a bromine, chlorine or iodine molecule * what reactions can haloalkanes undergo? * substitution reactions * substitution to alcohols

Reagent: KOH (alcoholic) * substitution to amides

Reagent: KOH(aq) or NaOH(aq) * elimination to alkenes

Reagent: concentrated NH3 (alcoholic) * how are haloalkanes formed? * addition/halogenation/bromination/chlorination reactions

Reagent: HBr, HCl, Br2 * substitution reactions

Reagent: conc HCl or SOCl2

isomerism :) * structural

same molecular formula, different structural formula * chain

the chain is branched differently * positional

the position of the functional group differs * functional

the functional group has changed * stereoisomerism

same molecular formula, atoms occupy different positions in space * geometric

occurs due to restricted rotation of C double bond, cis/trans * optical

occurs when molecules have a chiral centre as the carbon is bonded to four different atoms or molecules, producing two non-superimposable mirror images

How to tell enantiomers apart?

The enantiomers can be distinguished based on their ability to rotate plane polarised light. One enantiomer will rotate the plane-polarised light to the left, while the other enantiomer will rotate the plane-polarised light to the right.

When there are equal amounts of both enantiomers, the solution is called racemic and the light will not be rotated

reactions & reagents :) * reagents: * lucas reagent

the lucas reagent is used to identify 1°, 2° and 3° alcohols, it is ZnCl2 + conc HCl

3° alcohols - turns cloudy immediately

2° alcohols - turns cloudy within 3-5 minutes

1° alcohols. - no change, solution remains colourless

alcohol + HCl —ZnCl2—> haloalkane + water * damp litmus paper * amine

damp red paper turns blue * carboxylic acid

damp blue paper turns red * amide

no change * acyl chloride

damp blue paper turns red * universal indicator * amine

turns blue (basic) * carboxylic acid

orange or yellow (acidic) * amide

no change * acyl chloride

red (strong acid) * heat with acidified Cr2O72- * alcohol (primary)

partial oxidation reaction, solution goes from orange to green as an aldehyde forms, if a full oxidation reaction occurs, the solution goes from purple to colourless and a carboxylic acid is formed * alcohol (secondary)

oxidation reaction occurs and solution changes from orange to green as a ketone forms * alcohol (tertiary)

no reaction * aldehyde

oxidation reaction, solution goes from purple to colourless as carboxylic acid forms * ketone

no reaction * acyl chloride

vigorous exothermic reaction * heat with acidified MnO4- * alcohol (primary

partial oxidation reaction, solution goes from purple to colourless as aldehyde forms, if a full oxidation reaction occurs, a carboxylic acid will form * alcohol (secondary)

oxidation reaction occurs and solution changes colour from purple to colourless as a ketone forms * alcohol (tertiary)

no reaction * aldehyde

oxidation reaction, solution goes from purple to colourless as carboxylic acid forms * ketone

no reaction * acyl chloride

vigorous exothermic reaction * conc HCl * amine

white cloud forms * Cu2+ * amine

complex ions forms with a deep blue colour * warm with fehling’s/benedict’s solution - used to distinguish aldehydes from ketones * aldehyde

blue solution changes to a brick red precipitate * ketone

no reaction, solution remains blue * tollen’s reagent & heat - used to distinguish aldehydes from ketones * aldehyde

colourless solution forms silver mirror or black precipitate * ketone

no reaction * NH3 * acyl chloride

white fumes given off * water * amines

soluble * esters

insoluble and form a visible layer on top as they are less dense * acyl chlorides

vigorous exothermic reaction, fumes given off as carboxylic acid forms * reactions: * hydrolysis:

The reflux process is used because it ensures that volatile molecules are contained when the reaction is heated

As, it travels upwards, the vapour is condensed in the condenser, and drops back into the reaction mixture to be further oxidised * distillation

Distillation separates organic molecules by evaporating and condensing molecules based on boiling points. * w/ water * amine with water

eg: propanamine

H3CCH2CH2NH2 + H2O → H3CCH2CH2NH3+ + OH- * acyl chloride with water

eg: propanyl chloride

CH3COCl + H2O → CH3COOH + HCl * carboxylic acid with water

carboxylic acid + H2O → ← carboxylate ion + H3O+ (weak acids only partially dissociate)

eg: propanoic acid

C2H5COOH + H2O →← C2H5COO- + H3O+ * oxidation of alcohols * partial oxidation of primary alcohol

primary alcohol → aldehyde

RCH2OH → RCHO + 2e + 2H+

eg: propan-1-ol

reagent: KMnO4

C3H7OH → C3H6O + 2H+ + 2e * full oxidation of primary alcohol

primary alcohol → carboxylic acid

RCH2OH → RCOOH + 2e + 2H+

eg: propan-1-ol

reagent: KMnO4

C3H7OH → C2H5COOH + 2H+ + 2e * oxidation of secondary alcohol

secondary alcohol → ketone

RCH2OH → RCOR + 2e+ 2H+

eg: propan-2-ol

reagent: KMnO4

C3H7OH → C3H6O + 2H+ + 2e * aldehydes * silver mirror

tollens reagent is reduced by aldehydes to form a silver metal

Ag(NH3)2 + (aq) + e → Ag(s) + 2NH3(aq)

the aldehyde is oxidised to form a carboxylic acid

RCHO(aq) + 2OH- (aq) → RCOOH (aq) + H2O(l) + 2e

eg: propanal in tollens

CH3CH2CHO + Ag+ → RCOOH(aq) + Ag * fehlings/benedicts

the blue aqueous copper ions are reduces by aldehydes to form a red insoluble solid

2Cu2+ (aq) + 2OH-(aq) + 2e → Cu2O(s) + H2O(l)

condensation polymerisation:

small organic molecules join to make a large organic molecule, with the release of a small molecule (mainly H2O) for every amide link formed