Mechanisms

CH4

CHHHHCHHHHCHHHHHHHHCCHHHH

SN2

Nu
LG
LG
HHH
Nu
LG
H
Nu
δ+
δ
δ
State 1State 2State 3
Nu
Nu
LG
HHH
Nucleophile attacks an sp3 hybridized carbon.
δ+
δ
δ
Nu–C bond forms as CLG bond breaks through a single transition state.
Nu
LG
LG
HHH
δ+
δ
δ
Nu–C bond forms as CLG bond breaks through a single transition state.
Product forms with inverted stereochemistry. The leaving group departs with the bonding electrons.
Nu
LG
Nucleophile attacks an sp3 hybridized carbon.

Acetal Formation

OH
CH3O
HOHOHClHO+HOHCH3OHOHOHHHO+HHOHOHHOHO+HOHO+HCH3ClCH3OHO+HOHH
HCl
CH3OH
State 1State 2State 3State 4State 5State 6State 7State 8State 9State 10State 11State 12State 13State 14State 15
HOHOOH
CH3O
HCl
CH3OH
OHHOHClHOHO+ClHHOHOO+HClHHOO+HHOHCH3OHOHHOHCH3HO+HHO+HOHHO+HHO+HOHHHOHO+HO+HHHO+HOHCH3OHO+HCH3O+HOHO+HCH3ClCH3O+OHHClOHCH3
CH3O
OClH
HOHOOH
CH3O
HCl
CH3OH