CAPE CHEMISTRY UNIT 2 – ORGANIC



CAPE CHEMISTRY UNIT 2 – ORGANIC

EXAM REVISION MEMORY JOGGERS

A. REVIEW PAST TESTS

B. WORK PAST A-LEVEL QUESTIONS

C. WORK PAST CAPE QUESTIONS

D. MECHANISM

Use the mechanism work sheet – / examples / reactants / intermediate / products / arrows

- free radical substitution

- electrophillic addition

- electrophilic substitution

- nucleophilic addition

- nucleophilic substitution

E. STRUCTURE [molecular, condensed, displayed formulae]

• Aliphatic

- Chain: unbranched / branched

- Ring (e.g. cyclohexane, cyclohexene)

• Aromatic ring (e.g. benzene)

F. FORMULAE: empirical / molecular

G. NOMENCLATURE: Examples from each functional group

H. ISOMERISM

Structural

Chain isomerism – examples

Positional isomerism - examples

Functional isomerism – examples

Stereoisomerism

Geometric (cis / trans) isomerism (common in which groups of organic compounds)

Optical isomerism (common in which groups of organic compounds)

- optical activity

- chiral / achiral

- mirror image – superimposable / non-superimposable

- rotation of molecule with respect to mirror image – test for superimpisibility

- asymmetric carbon (a carbon atom bonded to four atoms or groups)

- enantiomer

- racemic mixture

I. FUNCTIONAL GROUP: Use the functional group work sheet – names and examples

Alkanes

1. characteristic features / reactions

2. halogenation / cracking / combustion

3. MECHANISM – free radical substitution [arrows]

Alkenes

1. characteristic features / reactions

2. reaction with liquid bromine (symmetrical and unsymmetrical alkene).

3. reaction with aqueous bromine (symmetrical and unsymmetrical alkene).

4. reaction with bromine in organic solvent (symmetrical and unsymmetrical alkene).

5. decipher structure / position of double bonds from reaction with

- potassium manganate (VII), cold, acidified

- potassium manganate (VII), hot, concentrated, acidified

- potassium manganate (VII), cold, alkaline

- potassium manganate (VII), cold, neutral

6. reaction with conc. Sulphuric acid

7. reaction with hydrogen halide (Markovnikov’s rule)

8. hydrogenation of fat

9. trans-fats

10. MECHANISM – BROMINE AND HYDROGEN BROMIDE (arrows)

Alcohols - characteristic features / reactions /

Halogenoalkanes - characteristic features / reactions

MECHANISM – nucleophilic substitution with hydroxyl ions (arrows)

Aldehydes and ketones - characteristic features / reactions

MECHANISM – nucleophilic addition with hydrogen cyanide (arrows)

Carboxylic acids - characteristic features / reactions

Esters - characteristic features / reactions

Amines - characteristic features / reactions

Phenol - characteristic features / reactions

J. BENZENE RING:

1. structure

2. bond length

3. bond strength

4. reactions that occur easily

5. effect of delocalized electrons – on substituents

6. effect of substituents - on delocalized electrons

7. MECHANISM - nitration of benzene and methylbenzene

8. benzene and methylbenzene with Br2 in FeBr3

9. nitrobenzene with Sn in conc. HCl

K. AMINO ACIDS

1. W hen are they ACIDIC / BASIC / NEUTRAL

2. polymerization

L. ZWITTERIONS – formation

M. DIAZONIUM COMPOUNDS / DYES – formation [reactants and products] / uses

N. MACROMOLECULES – categories / formation /

O. QUALITATIVE ORGANIC REACTIONS

1. identify aldehydes and ketones

2. distinguish between aldehyde and ketones

3. identify alcohol / aldehyde / ketone with –CH3 on alpha carbon

4. identify phenol

5. identify primary alcohol

6. identify secondary alcohol

7. identify tertiary alcohol

P. REAGENTS

The following reagents will react with which functional groups?

Identify the PRODUCTS formed and draw their STRUCTURE

- potassium manganate (VII), cold, acidified

- potassium manganate (VII), hot, acidified

- potassium manganate (VII), cold, alkaline

- potassium manganate (VII), cold, neutral

- potassium dichromate (VI), acidified

- Benedict’s reagent

- Fehling’s reagent

- Tollen’s reagent

- SOCl2

- PCl5

- Halogens (in their standard state)

- Aqueous bromine

- Hydrogen halides

- Conc. Sulphuric acid

- Iodine, alkaline

- Carboxylic acid

- Water

- Strong base

- Carbonate

- Hydrogen carbonate

- Brady’s reagent

- LiAlH4

- H2 / Pt

- HCN (NaCN / HCl)

Q. OXIDATION

Examples of oxidation reaction

R. REDUCTION

Examples of reduction reactions

S. ACID BASE STRENGTH

1. list the organic compounds with acidic characteristics

2. identify features of the compounds that determine acid strength (bond strength and ….)

3. list the factors that influence acid strength (halogens, etc.)

4. list the organic compounds with basic characteristics

5. identify features of the compounds that determine base strength (***)

6. list the factors that influence basic characteristics (888)

T. ACID BASE REACTIONS

- Examples of functional groups that react with strong acid

- Examples of functional groups that react with weak acid

- Examples of functional groups that react with strong base

- Examples of functional groups that react with strong base

U. REACTIVE METALS

- Example of functional groups that react with reactive metals

V. PROCESSES

1. condensation polymerization

- esters / nylon (polyamide) / protein (polyamide) / polysaccharide

2. addition polymerisation

3. esterification

4. base hydrolysis of ester

5. acid hydrolysis of ester

6. saponification

7. transesterification

W. CATALYSTS

1. Zeolite

2. FeBr3

X. SPECIAL EFFECTS

1. inversion - hydrolysis of halogenoalkanes

2. Markovnikov’s rule

3. Inductive effect

4. Conjugative effect

5. Optical activity

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