NCEA Chemistry Organics Level 3

Reaction scheme set up

Alkene + X2

Di(X) Alkane

Alkene + H2 (Conditions - Ni, 300 degrees)

Alkane

Alkene + HCl (in CCl4)

Haloalkane

Alkene + H2O (Conditions - Heat, ,dil. H2SO4)

Alcohol

Alkene + MnO4-/H+

Alcohol (diol)

Alkane + Cl2 (Conditions - UV)

Haloalkane

Alkane + Br2 (Conditions - UV (takes longer))

Haloalkane

Haloalkane + NH3(conc.) (Conditions - warm)

Aminoalkane + NH4X

Haloalkane + KOH/NaOH (alc.) (Conditions - Reflux)

Alkene + X- + Water

Haloalkane + KOH/NaOH (aq.) (Conditions - Reflux)

Alcohol + X-

1 Alcohol + Cr2O7(2-)/H+ (Conditions - cool)

Aldehyde

Alcohol (Conditions - 170 degrees, conc. H2SO4)

Alkene + Water

1 Alcohol + Cr2O7(2-)/H+ (Conditions - warm, reflux)

Carboxylic Acid

Alcohol + Carboxylic Acid (Conditions - Conc. H2SO4 (alc.)

Ester

2 Alcohol + Cr2O7(2-)/H+ (Conditions - Reflux)

Ketone

Aldehyde + Cr2O7(2-)/H+ (Conditions - Reflux)

Carboxylic Acid

Carboxylic Acid + PCl5/SOCl2

Acid Chloride

Carboxylic Acid + Base(aq.)/1 Amine/2 Amine

Carboxylate Salt

Carboxylate Salt (Heat)

1, 2, 3 Amino Acid

Acid Chloride + NH3 (alc.)/1 Amine/2 Amine

1, 2, 3 Amino Acid

Acid Chloride + Alcohol

Ester

Ester + NH3 (alc.)

Amino Acid

Ester + dil. H+ (aq.)

Carboxylic Acid

Acid Chloride + Water

Carboxylic Acid

Alcohol + PCl3 (Reflux)

Chloroalkane + H3PO3

Alcohol + PCl5 (Reflux)

Chloroalkane + POCl3 + HCl

Alcohol + SOCl2 (Reflux)

Chloroalkane + HCl + SO2

Alcohol + Chloroalkane

Ester

1 Amine + Haloalkane

2 Amine + HX

Amine + Water

R-NH3 + OH-

Amine + HCl

R-NH3 + Cl-

Amine + Cu(2+)(aq.)

[Cu(R-NH2)4](2+)

Tollens Test;

Aldehyde (-al) + 2[Ag(NH3)2]+(aq.) + Water + 2H+(aq.)

Carboxylic Acid + 2Ag + 4NH4(+)

Silver Mirror produced

Benedicts;

Aldehyde + 4OH-(aq) + 2Cu(2+)(aq.)

Blue Solution

Carboxylic Acid + Cu2O + 2H2O

Orange Precipitate

Homologous series

A family of organic compounds having the same functional group but differing by the number of CH2- units.

Isomerism

Species which have the same formula but atoms are arranged in a different way.

Structural Isomerism

Molecules containing the same atoms but the atoms are 'connected' in a different order, they have the same molecular formula.

Stereoisomers (Geometric and Enantiomers)

Molecules containing the same atoms or groups of atoms which have different spatial arrangements.

Chiral C Atom

A C atom with four different groups attached.

Reflux

To boil (a liquid) in a vessel attached to a condenser so that the vapors continuously condense for reboiling, or run off allowing two different species to be seperated due to their differing boiling points. Water always goes in at the lowest point.

Peptide Link

A carboxyl and an amino group react to form an amide (or peptide link) (-CONH-). The formation of many of these links produces a polyamide.

Optical Isomers

Have identical chemical and physical properties, except the two isomers will rotate plane-polarised light in opposite directions. They also react differently with enzymes in biological systems.

Addition Reactions

Atoms or groups of atoms are added to an unsaturated molecule to give one product.

Elimination

A small molecule is lost to produce an unsaturated molecule and a small byproduct.

(Nucleophilic) Substitution

A group on the molecule is replaced by another group (which is a nucleophile).

Nucleophile

A negatively charged ion or polar molecule with one or more lone pairs of electrons that is attracted to a + carbon atom.

Condensation

Two larger molecules are joined together with the elimination of a smaller molecule. An example is peptide formation.

Polymerisation

a) Addition polymerisation involves the joining of alkene monomers by addition, forming a long chain molecule eg polythene is formed from many ethene monomers.

b) Condensation polymerisation involves the joining of monomers by a series of condensation reactions eg dialcohol plus diacid forms a polyester, dialcohol plus diamine forms a polyamide, amino acids linking forms a protein.

Acid-base reactions

The carboxylic acid functional group is weakly acidic. It will donate a proton to water forming a solution that contains the carboxylate ion, RCOO- and H3O+ and has a pH less than 7.

The amino group is basic and accepts a proton from water forming RNH3+ and OH- which makes the solution basic with a pH greater than 7.

Polymer

A very large molecule made by joining many small molecules together.

Polyamide

A polymer containing many amide (-CONH- or -CONR-) links.

Polyester

A polymer containing many ester (-COO-) links.