Organic Chemistry Reagent Flashcards

Alkyl Halides and Alcohol Reactions

• Alkyl halide (methyl/1° unhindered) reacts with NaOH to form alcohol via Sn2 mechanism.
• Alkyl halide (1° hindered/2°) undergoes reaction with NaOAc and NaOH, resulting in alcohol through Sn2 then SnAc processes.
• Alkyl halide (3°) treated with H2O yields alcohol via Sn1 or E1 pathways.

Alcohol to Alkene Conversion

• Alcohol to alkene reaction achieves the most stable Zaitsev product using H2SO4 and heat.
• Alcohol transforms into alkyl halide using HCl (H-X); primary alcohols follow Sn2, while secondary and tertiary follow Sn1.

Alcohol Halogenation Reactions

• Alcohol reacts with PBr3 or PCl3 to yield alkyl halide, involving Sn2 mechanism with inversion at alpha carbon.
• Using SOCl2 and pyridine produces alkyl halide along with protonated pyridine and Cl ion, involving SnAc and Sn2 (inversion).
• ClMs, ClTs, or TfOTf applications yield alkyl halide with no change at the alpha carbon through SnAc and acid/base reactions.

Ether Reactions

• Unhindered alkyl halide produces Williamson ether using a strong alkoxide nucleophile.
• Symmetric ether reacts with H2SO4 and H2O to yield alkyl halide via Sn1 mechanism.

Epoxide Reactions

• Epoxide converts to alcohol through Sn2, with nucleophile attacking the less substituted side using strong bases like RS-, RO-, or OH-.
• Using strong acid (HCl) facilitates conversion of epoxide to alcohol with nucleophile attacking the more substituted side.

Ester and Carboxylic Acid Reductions

• Ester reduction forms 1° alcohol with two equivalents of LiAlH4.
• To yield 3° alcohol from ester, two organometallic reagents are used.
• Carboxylic acid reduction to 1° alcohol also requires two equivalents of LiAlH4.
• Aldehyde reduces to 1° alcohol utilizing either LiAlH4 or NaBH4; conversion to 2° alcohol requires organometallic reagents.
• Ketone reduces to 2° alcohol with LiAlH4 or NaBH4, while producing a 3° alcohol involves organometallic reagents.

Alcohol Oxidation

• 1° alcohol oxidation results in carboxylic acid through the Jones oxidation process.
• PCC is utilized to oxidize 1° alcohol to aldehyde.
• Jones or PCC can oxidize 2° alcohol into a ketone.
• Aldehyde oxidizes to carboxylic acid using Jones or Tollen's reagent (more selective).

Organometallic Chemistry

• Organometallic compounds such as R-MgBr, R-Li, and R-C≡C-Na are key reagents in various reduction reactions.
• Carboxylic acid to carboxylate conversion requires organometallic reagents.

Reaction Mechanisms and Products

• b-Hydroxy carbonyl converts to a,b-unsaturated carbonyl catalyzed by NaOH, heat, and water.
• Two aldehydes/ketones yield b-hydroxy carbonyl under NaOH and water catalysis.
• Two aldehydes/ketones can produce a,b-unsaturated carbonyl with acidic conditions (H3O+, H2O).
• Conditions may lead to multiple messy products with two aldehydes/ketones treated with NaOH, heat, and water.
• If alpha H's on carbon attached to C=O are present, use nucleophiles; otherwise, participate as an electrophile under NaOH, heat, and water.

Addition Reactions of Enones

• Enone to carbonyl type conversion can occur via 1,2 addition yielding less stable alkene using LiAlH4, R-MgBr, or R-Li.
• For more stable alkene formation (1,4 addition), utilize good nucleophiles and weak bases such as RS-, -CN, R2NH, or HBr.