Organic Chemistry

Key Terms 177

c.Addition of halogen ( is the electrophile; Section 4.7)

d.Acid-catalyzed addition of water and alcohols ( is the electrophile; Section 4.5)

e.Addition of water and alcohols: oxymercuration–reduction and alkoxymercuration–reduction (Hg is the electrophile and is

replaced by H in the second step; Section 4.8)

f. Hydroboration–oxidation (B is the electrophile and is replaced in the second step by OH; Section 4.9)

2. Addition of hydrogen ( is the electrophile; Section 4.11)

RCH CH 2 + H 2 RCH 2 CH 3

Pd/C, Pt/C, or Ni

H–

RCH CH 2 RCH 2 CH 2 OH

1. BH 3 /THF


2. HO−, H 2 O 2 ,^ H 2 O

RCH CH 2 RCHCH 3

1. Hg(OAc) 2 , H 2 O,THF
   2. NaBH 4
   OH

RCH CH 2

1. Hg(O 2 CCF 3 ) 2 , CH 3 OH
   2. NaBH 4 RCHCH^3
   OCH 3

RCH CH 2 + H 2 O RCHCH 3

OH

RCH CH 2 CH 3 OH RCHCH 3

H+

+

OCH 3

H+

H+

RCH CH 2 Cl (^2) CH RCHCH 2 Cl
2 Cl 2
CH 2 Cl 2

• Cl
  RCH CH 2 + Br 2 RCHCH 2 Br
  Br
  RCH CH 2 + Br (^2) H 2 O RCHCH 2 Br
  OH
  Br+ or Cl+
  Key Terms
  acid-catalyzed reaction (p. 152)
  alkoxymercuration–reduction (p. 162)
  carbene (p. 167)
  carbocation rearrangement (p. 155)
  catalyst (p. 152)
  catalytic hydrogenation (p. 171)
  concerted reaction (p. 164)
  constitutional isomers (p. 148)
  dimer (p. 164)
  electrophilic addition reaction (p. 141)
  free radical (p. 168)
  halohydrin (p. 159)
  Hammond postulate (p. 145)
  heat of hydrogenation (p. 172)
  heterogeneous catalyst (p. 171)
  heterolysis (p. 168)
  heterolytic bond cleavage (p. 168)
  homolysis (p. 168)
  homolytic bond cleavage (p. 168)
  hydration (p. 151)
  hydroboration–oxidation (p. 163)
  hydrogenation (p. 171)
  hyperconjugation (p. 144)
  initiation step (p. 170)
  Markovnikov’s rule (p. 148)
  mechanism of the reaction (p. 142)
  1,2-hydride shift (p. 155)
  1,2-methyl shift (p. 155)
  oxymercuration–reduction (p. 161)
  pericyclic reaction (p. 164)
  peroxide effect (p. 170)
  primary alkyl radical (p. 168)
  primary carbocation (p. 143)
  propagation step (p. 170)
  radical (p. 168)
  radical addition reaction (p. 168)
  radical chain reaction (p. 170)
  radical inhibitor (p. 170)
  radical initiator (p. 170)
  reduction reaction (p. 162)
  regioselective reaction (p. 148)
  secondary alkyl radical (p. 168)
  secondary carbocation (p. 143)
  steric effects (p. 165)
  steric hindrance (p. 165)
  termination step (p. 170)
  tertiary alkyl radical (p. 168)
  tertiary carbocation (p. 143)