organic

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

acyl chloride to amide

substitution with conc NH3 (alcoholic)

acyl chloride + NH3 (alcoholic)

substitution to amide

acyl chloride to carboxylic acid

substitution/hydrolysis with H2O

acyl chloride + H20

substitution to carboxylic acid

alcohols

carbon molecules bonded to an OH molecule

alcohol + conc H2SO4 (alcoholic)

elimination/dehydration/condensation to alkene

alcohol to alkene

elimination reaction with conc H2SO4 (alcoholic)

alcohol to haloalkane

substitution with conc HCl or SOCl2

alcohol + HCl/SOCl2

substitution to haloalkane

alcohol to ester

substitution/esterification/condensation with carboxylic acid and conc H2SO4

alcohol + carboxylic acid and conc H2SO4

substitution to ester

alcohol 1° + MnO4-/H+ or Cr2O72-/H+ heat in reflux

total oxidation to carboxylic acids

alcohol 1° to carboxylic acid

total oxidation with MnO4-/H+ or Cr2O72-/H+ in reflux

alcohol 1° + MnO4-/H+ or Cr2O72-/H+ warm gently and distil

1**°** partial oxidation to aldehydes

Observations: orange Cr2O72- reduces to green Cr3+ ion

or purple MnO4- reduces to colourless Mn2+ ions

alcohol 1° to aldehyde

partial oxidation with MnO4-/H+ or Cr2O72-/H+ warm gently and distil

alcohol 2° to ketone

full oxidation with KMnO4/H+ or K2Cr2O7/H+

alcohol 2° + KMnO4/H+ or K2Cr2O7/H+

full oxidation to ketone

aldehydes

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

aldehyde to carboxylic acid

oxidation with MnO4-/H+ or Cr2O72-/H+ or tollens (Ag+) or Fehlings (Cu2+) or benedicts (Cu2+)

aldehyde + MnO4-/H+ or Cr2O72-/H+ or tollens (Ag+) or Fehlings (Cu2+) or benedicts (Cu2+)

oxidation to carboxylic acid

aldehyde to alcohol

reduction with NaBH4

aldehyde + NaBH4

reduction to alcohol

alkenes

unsaturated hydrocarbons that primarily consist of hydrogen and carbon and contain a double carbon bond

alkene + MnO4-/H+

oxidation where many small monomer unsaturated alkenes bond together to form a long polymer chain

alkene to polymer

oxidation with MnO4-/H+

alkene + dilute H2SO4 and nickel/platinum catalyst

addition/hydrogenation to alcohols

alkene to alcohol

addition with dilute H2SO4 and nickel/platinum catalyst

alkene to haloalkane

addition/hydrogenation/bromination/chlorination with HBr, HCl, Br2

alkene + HBr, HCl, Br2

addition to haloalkane

alkene addition rules

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. symmetrical vs asymmetrical

amide

a carbon double bonded to oxygen at the edge of the molecule, this carbon is also bonded to an NH2 ammonia group

amines

a carbon chain bonded to a NH2 ammonia molecule

they have higher boiling points then alkanes, but lower than alcohols

carboxylic acids

a carbon double bonded to oxygen at the edge of the molecule, this carbon atom is also bonded to an OH hydroxide molecule

carboxylic acid to acyl chloride

substitution with SOCl2

carboxylic acid + SOCl2

substitution to acyl chloride

carboxylic acid to amide

substitution with NH3 and heat

carboxylic acid + NH3 and heat

substitution to amide

carboxylic acid to ester

substitution/esterification/condensation with alcohol and H2SO4

carboxylic acid + alcohol & H2SO4

substitution to ester

diols

are formed by oxidation from alkenes, with reagent MnO4-/H+ 

esters

a carbon double bonded to an oxygen molecule in the molecule, this carbon is also bonded to another oxygen atom

ketones

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

they are less reactive than aldehyde

ketone to alcohol

reduction with NaBH4r

ketone + NaBH4

reduction to alcohol

haloalkanes

a carbon chain bonded to a bromine, chlorine or iodine molecule

haloalkane to alcohol

substitution with KOH (aqueous)

haloalkane with KOH (aqueous)

substitution to alcohols

haloalkane to amine

substitution with conc NH3 (alcoholic)

haloalkane + conc NH3 (alcoholic)

substitution to amine

haloalkane to alkene

elimination with conc NH3 (alcoholic)

chain isomerism

structural isomerism where the chain is branched differently

positional isomerism

structural isomerism where the position of the functional group differs

functional isomerism

structural isomerism where the functional group has changed

structural isomerism

same molecular formula, different structural formula

stereoisomerism

same molecular formula, atoms occupy different positions in space

geometric isomerism

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

optical isomerism

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

enantiomer differences

One enantiomer will rotate the plane-polarised light to the left, while the other enantiomer will rotate the plane-polarised light to the right.

equal enantiomers

the solution is called racemic and the light will not be rotated

lucas reagent purpose

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

lucus reagent and 3° alcohols

turns cloudy immediately

lucus reagent and 2° alcohols

turns cloudy within 3-5 minutes

lucus reagent and 1° alcohols

no change, solution remains colourless

acyl chloride pH

acidic, turns blue litmus paper red & universal indicator red

primary alcohol & heat w/ Cr2O72-/H+

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

secondary alcohol & heat w/ Cr2O72-/H+

oxidation reaction occurs and solution changes from orange to green as a ketone forms

aldehyde & heat w/ Cr2O72-/H+

oxidation reaction, solution goes from orange to green as carboxylic acid forms

acyl chloride & heat w/ Cr2O72-/H+ (or MnO4-)

vigorous exothermic reaction

primary alcohol & heat w/ MnO4-/H+

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

secondary alcohol & heat w/ MnO4-/H+

oxidation reaction occurs and solution changes colour from purple to colourless as a ketone forms

aldehyde & heat w/ MnO4-/H+

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

amine & conc HCl

white cloud forms amine

amine & conc HCl

complex ions forms with a deep blue colour

fellings/benedicts purpose

warm with solution - used to distinguish aldehydes from ketones

fellings/benedicts + ketone

no reaction, solution remains blue

fellings/benedicts + aldehyde

blue solution changes to a brick red precipitate

tollens purpose

& heat - used to distinguish aldehydes from ketones

tollens + ketone

no reaction

tollens + aldehyde

colourless solution forms silver mirror or black precipitate

acyl chloride & NH3

white fumes given off

amine & water

soluble

ester & water

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

acyl chloride & water

vigorous exothermic reaction, fumes given off as carboxylic acid forms

hydrolysis

A hydrolysis reaction uses water to split a large organic molecule into smaller organic molecules. Both acidic and basic hydrolysis require heat under reflux.

acidic hydrolysis of amide

protonates N atoms to produce ammonium ions

basic hydrolysis of amide

produces amine and carboxylate ion

basic hydrolysis of ester

requires a dilute base (e.g KOH(aq) to produce an alcohol and a carboxylate ion. COOH loses a hydrogen atom.

acidic hydrolysis of ester

requires a dilute acid (e.g. dil. H2SO4) to produce an alcohol and carboxylic acid. The C=O gains –OH from water, and the C–O gains –H from water.

reflux purpose

is used to ensure that volatile molecules are contained when the reaction is heated, increasing the yield as no molecules are lost - oxidation reaction

reflux process

As molecules travel upwards, the vapour is condensed in the condenser, and drops back into the reaction mixture to be further oxidised

distillation

separates organic molecules by evaporating and condensing molecules based on boiling points, before they can be further oxidised - oxidation reaction

condensation polymerisation

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

aqueous conditions

acyl chloride to carboxylic acid because of OH- group

aldehyde + reagent

carboxylic acid forms in an oxidation reaction

monomers have 2 functional groups

so each molecule has a second reaction site that can react to the next adjacent molecule to from a polymer