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& Answers 2025
conc. H₂SO₄, heat - CORRECT ANSWER ✅E Alcohol --> Alkene regioselective - more substituted double bond stereoselective - trans(E)>cis(Z) Rearrangement around tertiary alcohol HCl - CORRECT ANSWER ✅Sn Alcohol --> Alkyl halide regioselective - tertiary alcohol HBr (3) - CORRECT ANSWER ✅Sn1/Sn2: Alcohol --> Alkyl halide Sn1- secondary and tertiary, Sn2 - primary Free Radical: Alkene --> alkyl bromide markovnikov HBr Addition: Alkyne --> alkene markovnikov, anti-addition
& Answers 2025
SOCl₂, base - CORRECT ANSWER ✅Sn Alcohol --> Alkyl chloride primary and secondary alcohols PBr₃ - CORRECT ANSWER ✅Sn Alcohol --> alkyl bromide primary and secondary alcohol Na₂Cr₂O₇ or CrO₃, H₂SO₄ ** - CORRECT ANSWER ✅oxidation alcohol --> carbonyl produces carboxylic acid in the presence of water when primary H₂CrO₄ - CORRECT ANSWER ✅oxidation alcohol --> carbonyl produces carboxylic acid in the presence of water when primary PCC or PDC, CH₂Cl₂ - CORRECT ANSWER ✅oxidation alcohol --> carbonyl HIO₄ - CORRECT ANSWER ✅oxidation
& Answers 2025
1. BH₃, THF
- H₂O₂, NaOH - CORRECT ANSWER ✅Hydrobroration alkene --> alcohol anti-markovnikov, syn-addition H: hydride shift, OH: water dilute H₂SO₄ - CORRECT ANSWER ✅Acid-Catalyzed alkene --> alcohol markovnikov OsO₄, catalyst - CORRECT ANSWER ✅Hydroxylation Alkene --> Alcohol (2) syn-addition Br₂ or Cl₂, H₂O, CH₂Cl₂, cold/dark - CORRECT ANSWER ✅Electrophilic addition alkene --> alcohol/alkyl halide Alcohol: Markovnikov Halide: anti-Markovnikov
& Answers 2025
anti-addition Br₂ or Cl₂, CH₂Cl₂, cold/dark - CORRECT ANSWER ✅Electrophilic addition alkene --> alkyl halide (2) anti-addition H₂, metal catalyst (2) - CORRECT ANSWER ✅Hydrogenation... Alkene --> alkane syn-addition Hydrogenation... carbonyl --> alcohol Peroxyacetic Acid (RC(=O)OOH) - CORRECT ANSWER ✅Epoxidation Alkene --> Epoxide Same side of DB = same side of ring
- O₃
- H₂O, Zn or S(CH₃)₂ - CORRECT ANSWER ✅Oxidative Cleavage Alkene --> Ketone or Aldehyde
& Answers 2025
NaOH - CORRECT ANSWER ✅Sn vicinal halohydrin--> epoxide Backside attack Halide and oxygen must be anti inversion of configuration H₂SO₄, HOCH₂CH₃ - CORRECT ANSWER ✅ring-opening Epoxide --> alcohol markovnikov
- NaOCH₂CH₃, HOCH₂CH₃
- Aqueous Acid - CORRECT ANSWER ✅ring-opening Epoxide --> alcohol anit-markovnikov
- Organometallic (Grignard)
- Acid Workup - CORRECT ANSWER ✅Grignard Carbonyl --> Alcohol anion attacks C; hydrogen on oxygen results from acid workup
& Answers 2025
- LiAlH₄
- Acid Workup - CORRECT ANSWER ✅LiAH Carbonyl --> alcohol hydrogen attacks C; hydrogen on oxygen results from acid workup NaI, acetone - CORRECT ANSWER ✅Sn bromide --> iodide inversion of configuration NaNH₂, NH₃ - CORRECT ANSWER ✅Alkyne --> Alkyne (-) Excess of H₂, Pd - CORRECT ANSWER ✅Hydrogenation Alkyne --> alkane H₂, Lindlar Pd - CORRECT ANSWER ✅Semi-Hydrogenation Alkyne --> Alkene Cis Na, NH₃ - CORRECT ANSWER ✅Semi-Hydrogenation alkyne --> alkene
& Answers 2025
Alkene --> alkyl bromide anti-markovnikov HBr Addition: alkyne --> alkene anti-markovnikov
- BH₃-THF
- NaOH, H₂O₂ - CORRECT ANSWER ✅alkene --> alcohol anti-markovnikov syn-addition H₂SO₄, heat - CORRECT ANSWER ✅ether synthesis 2 alcohols --> ether only works with symmetrical, primary alcohols
