Advices For Studying Organic Chemistry

Table 6.6 Factors Favoring SN1 versus SN2 Reactions

Factor SN 1 SN 2

Substrate 3° (requires formstable carbocation) ation of a relatively Methyl > 1° > 2° (requires unhindered substrate)

Nucleophile

Weak Lewis base, neutral molecule,

nucleophile may be the solvent

(solvolysis)

Strong Lewis base, rate favored by

high concentration of nucleophile

Solvent Polar protic (e.g. alcohols, water) Polar aprotic (e.g. DMF, DMSO)

Leaving group (^) (the weaker the base after departs, the better the leaving group) I > Br > Cl > F for both SN1 and SN^2

6.15 ORGANIC SYNTHESIS: FUNCTIONAL GROUP

TRANSFORMATIONS USING SN 2 REACTIONS

1. Functional group transformation (interconversion): (Figure 6.13)


2. Alkyl chlorides and bromides are easily converted to alkyl iodide by SN2 reaction

R X

R OH

OR'

SH

SR'

C

C

OCR'

NR' 3 X−

N 3

N

CR'

O

OH−

SH−

CN−

R' C C−

R'CO−

O

NR' 3

N 3 −

Al

R'O−

R'S−

R R R R R R R R

− X−

(R=Me, 1o, or 2o)

(X=Cl, Br, or I)

Alcohol

Ether

Thiol

Thioether

Nitrile

kyne

Ester

Quaternary ammonium halide

Alkyl azide

Figure 6.13 Functional group interconversions of methyl, primary, and secondary
alkyl halides using SN2 reactions.