Organic Chemistry Reagents
Formulas with Correct Reactions
dilute H₂SO₄ - Answer- Acid-Catalyzed
alkene --> alcohol
markovnikov
OsO₄, catalyst - Answer- Hydroxylation
Alkene --> Alcohol (2)
syn-addition
Br₂ or Cl₂, H₂O, CH₂Cl₂, cold/dark - Answer- Electrophilic addition
alkene --> alcohol/alkyl halide
Alcohol: Markovnikov
Halide: anti-Markovnikov
anti-addition
Br₂ or Cl₂, CH₂Cl₂, cold/dark - Answer- Electrophilic addition
alkene --> alkyl halide (2)
anti-addition
H₂, metal catalyst (2) - Answer- Hydrogenation...
Alkene --> alkane
syn-addition
Hydrogenation...
carbonyl --> alcohol
Peroxyacetic Acid (RC(=O)OOH) - Answer- Epoxidation
Alkene --> Epoxide
Same side of DB = same side of ring
1. O₃
2. H₂O, Zn or S(CH₃)₂ - Answer- Oxidative Cleavage
Alkene --> Ketone or Aldehyde
1. O₃
2. H₂O - Answer- Ozonolysis
Alkene --> Ketone or Carboxylic Acid
Oxonolysis
Alkyne --> Carboxylic Acids
, H₂O - Answer- Hydrolysis
Alkyl halide --> alcohol
Strong Base, Heat - Answer- E2
Alkyl halide --> alkene
more substituted double bond
trans (E)>cis(Z)
Beta hydrogen and halide MUST be anti
Williamson Ether Synthesis - Answer- Sn2
alkoxide ion + alkyl halide --> Ether
regioselective: primary alkyl halides
NaOH - Answer- Sn2
vicinal halohydrin--> epoxide
Backside attack
Halide and oxygen must be anti
inversion of configuration
H₂SO₄, HOCH₂CH₃ - Answer- ring-opening
Epoxide --> alcohol
markovnikov
1. NaOCH₂CH₃, HOCH₂CH₃
2. Aqueous Acid - Answer- ring-opening
Epoxide --> alcohol
anit-markovnikov
1. Organometallic (Grignard)
2. Acid Workup - Answer- Grignard
Carbonyl --> Alcohol
anion attacks C; hydrogen on oxygen results from acid workup
1. LiAlH₄
2. Acid Workup - Answer- LiAH
Carbonyl --> alcohol
hydrogen attacks C; hydrogen on oxygen results from acid workup
NaI, acetone - Answer- Sn2
bromide --> iodide
inversion of configuration
NaNH₂, NH₃ - Answer- Alkyne --> Alkyne (-)
Excess of H₂, Pd - Answer- Hydrogenation
Formulas with Correct Reactions
dilute H₂SO₄ - Answer- Acid-Catalyzed
alkene --> alcohol
markovnikov
OsO₄, catalyst - Answer- Hydroxylation
Alkene --> Alcohol (2)
syn-addition
Br₂ or Cl₂, H₂O, CH₂Cl₂, cold/dark - Answer- Electrophilic addition
alkene --> alcohol/alkyl halide
Alcohol: Markovnikov
Halide: anti-Markovnikov
anti-addition
Br₂ or Cl₂, CH₂Cl₂, cold/dark - Answer- Electrophilic addition
alkene --> alkyl halide (2)
anti-addition
H₂, metal catalyst (2) - Answer- Hydrogenation...
Alkene --> alkane
syn-addition
Hydrogenation...
carbonyl --> alcohol
Peroxyacetic Acid (RC(=O)OOH) - Answer- Epoxidation
Alkene --> Epoxide
Same side of DB = same side of ring
1. O₃
2. H₂O, Zn or S(CH₃)₂ - Answer- Oxidative Cleavage
Alkene --> Ketone or Aldehyde
1. O₃
2. H₂O - Answer- Ozonolysis
Alkene --> Ketone or Carboxylic Acid
Oxonolysis
Alkyne --> Carboxylic Acids
, H₂O - Answer- Hydrolysis
Alkyl halide --> alcohol
Strong Base, Heat - Answer- E2
Alkyl halide --> alkene
more substituted double bond
trans (E)>cis(Z)
Beta hydrogen and halide MUST be anti
Williamson Ether Synthesis - Answer- Sn2
alkoxide ion + alkyl halide --> Ether
regioselective: primary alkyl halides
NaOH - Answer- Sn2
vicinal halohydrin--> epoxide
Backside attack
Halide and oxygen must be anti
inversion of configuration
H₂SO₄, HOCH₂CH₃ - Answer- ring-opening
Epoxide --> alcohol
markovnikov
1. NaOCH₂CH₃, HOCH₂CH₃
2. Aqueous Acid - Answer- ring-opening
Epoxide --> alcohol
anit-markovnikov
1. Organometallic (Grignard)
2. Acid Workup - Answer- Grignard
Carbonyl --> Alcohol
anion attacks C; hydrogen on oxygen results from acid workup
1. LiAlH₄
2. Acid Workup - Answer- LiAH
Carbonyl --> alcohol
hydrogen attacks C; hydrogen on oxygen results from acid workup
NaI, acetone - Answer- Sn2
bromide --> iodide
inversion of configuration
NaNH₂, NH₃ - Answer- Alkyne --> Alkyne (-)
Excess of H₂, Pd - Answer- Hydrogenation
