Topic 14: Carbon Chemistry SMK SACRED HEART, SIBU

Tetravalent
1. Carbon forms organic compound Small Size HCH3 is 1oC
Catenate RCH3 is 1oC
Empirical Formula % by mass , Mass of CO2 and H2O R2CH2 is 2oC
2. Chemical formula Molecular Formula Empirical F, Combustion analysis R3CH is 3oC
Structural Formula Displayed , Condensed , Skeletal R4C is 4oC
C and C
+ Stability: 3 > 2 > 1 > CH3
o o o R

3. Carbon species E+ = Lewis acid

C Stability: 3 < 2 < 1 < CH3
o o o Nu = Lewis base

Chain Change in Carbon skeleton

Structural Position Change in position of functional group
Functional Group (a) Alkene & Cycloalkane
(b) Alcohol & Ether
(c) Aldehyde & Ketone
(d) Carbocylic acid & Ester

trans cis
4. Isomerism
Geometrical

Higher m/p Higher b/p

Closely pack More polar
Stereoisomerism Symmertical
VDWF

Optical

Positive EWG increases acid strength / decreases pKa

Inductive Eg: Phenyl group, Hydroxyl group, Nitro- group
effect
when no. of EDG / Size of alkyl group / Distance
Negative EDG decreases acid strength / decreases pKb
Eg: alkyl group and cycloalkyl group

when no. of EWG / Electronegativity / Distance

5. Acid/Base Formation of more stable RCOO - , C6H5O - , C6H5NH2

Resonance
Strength effect Eg: RCOOH + H2O RCOO + H3O+ Equilibrium shift to right

Increasing acid strength : ROH < H2O < phenol < RCOOH < Benzoic acid

Attached to benzene ring Resonance Electron from O delocalises

6. EDG/EWG
(-OH is EDG) into benzene ring
eg: -OH

Not attached to benzene ring Inductive Increases acid strength

(-OH is EWG) effect