Chem 2211 Synthesis Reactions

NaNH₂ , THF

Ketone/Aldehyde + ROH + H₂O

Ketal/Acetal

Ketone/Aldehyde + ROH + RO^-

Hemiketal/Hemiacetal

H₂CrO₄, H₂O

NaBH₄, CH₃OH or 1.) LiAlH₄, Et₂O 2.) HCl, H₂O

H₂, Rh

H₂, Pd

NaBH₄, CH₃OH or 1.) LiAlH₄, Et₂O 2.) HCl, H₂O

Acidic conditions

HCl, Zn(Hg)

Basic conditions

N₂H₄, KOH

NaBH₃CN, CH₃OH, HCO₂H

X₂, CH₃CO₂H (Acidic conditions)

X₂, aq. NaOH (Basic conditions)

Grignard Reagant + CO_{2, then acidic workup}

Carboxylic acid functional group

1.) LiAlH₄, Et₂O 2.) HCl, H₂O (NaBH₄ +etc. not reactive enough)

H₂SO₄ (cat.)

SOCl₂

H₂O (pyridine can be added as “HCl Sink”

H₂O (Can be acid catalyzed, ex: HCl)

H₂O, H₂SO₄ (cat.) (or other catalytic acid)

HCl or NaOH (acidic or basic conditions), H₂O, heat

1.) H₂O, HCl, warm 2.) H₂O, HCl, heat

NaOH, H₂O, heat

CH₃OH, pyridine

acid or base catalyst (acid ex: H₂SO₄) (base ex: NaOH)

dry HCl catalyst

CHCl₃, KO-t-Bu (trans becomes trans, cis becomes cis) (can use other halogens)

CH₂I₂, Zn(Cu), Et₂O (stereospecific, trans to trans, cis to cis)