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Formula Sheets / Chemistry

Chapter 13

General Organic Chemistry

Revise with flashcards Download this chapter (PDF) All Chemistry formulas (PDF)

Electronic effects and intermediates Acidity, basicity and aromaticity Isomerism Nomenclature

Electronic effects and intermediates

Inductive (−I)
$-$ NO $_{2} > -$ CN $> -$ COOH $> -$ F $> -$ Cl $> -$ Br $> -$ I $> -$ OH
+I
$-$ C(CH $_{3})_{3} > -$ CH(CH $_{3})_{2} > -$ CH $_{2}$ CH $_{3} > -$ CH $_{3}$
Carbocation stability
$3^{\circ} > 2^{\circ} > 1^{\circ} >$ CH $_{3}^{+};$ benzyl, allyl stabilised by resonance
Carbanion stability
CH $_{3}^{-} > 1^{\circ} > 2^{\circ} > 3^{\circ}$
Hyperconjugation
number of $α$ -H atoms $\Rightarrow$ more stable carbocation / alkene

Acidity, basicity and aromaticity

Hückel's rule
$(4 n + 2) π$ electrons, planar, cyclic, fully conjugated $\Rightarrow$ aromatic $;$ $4 n π \Rightarrow$ antiaromatic
Acidity
RCOOH $>$ PhOH $>$ H $_{2}$ O $>$ ROH $>$ HC $\equiv$ CH
electron-withdrawing groups raise acidity; donating groups raise basicity
Amine basicity (aqueous)
$2^{\circ} > 1^{\circ} > 3^{\circ} >$ NH $_{3} ($ methyl amines $);$ aniline is much weaker

Isomerism

Stereoisomers
max $= 2^{n} (n =$ chiral centres; fewer if a meso form exists $)$
Degree of unsaturation
DU $= C - \frac{H}{2} - \frac{X}{2} + \frac{N}{2} + 1$
Priority (CIP)
higher atomic number first $; R :$ clockwise $, S :$ anticlockwise (lowest away)

Nomenclature

Functional group priority
COOH $>$ SO $_{3}$ H $>$ anhydride $>$ ester $>$ acid halide $>$ amide $>$ CN $>$ CHO $>$ C=O $>$ OH $>$ NH $_{2}$

p Block Elements (Group 13 and 14)Hydrocarbons