Recognizing Strong/Weak Nucleophiles/bases

Here's a list of common reagents to recognize for reactions, categorized by their nucleophilicity and basicity:

Strong Nucleophiles

• I⁻ (Iodide ion)

• HS⁻ (Hydrosulfide ion)

• RS⁻ (Thiolate ion)

• CN⁻ (Cyanide ion)

• N₃⁻ (Azide ion)

Strong Bases

• OH⁻ (Hydroxide ion)

• RO⁻ (Alkoxide ion, e.g., CH₃O⁻)

• NH₂⁻ (Amide ion)

• LiAlH₄ (Lithium aluminum hydride)

• NaH (Sodium hydride)

Bulky Bases

• t-BuO⁻ (tert-Butoxide ion)

• LDA (Lithium diisopropylamide)

• ((CH₃)₃Si)₂NLi (Lithium bis(trimethylsilyl)amide)

Weak Nucleophiles

• H₂O (Water)

• ROH (Alcohols)

• RCOOH (Carboxylic acids)

Weak Bases

• NH₃ (Ammonia)

• C₅H₅N (Pyridine)

• CH₃NH₂ (Methylamine)

• NaHCO₃ (Sodium bicarbonate)

• Mg(OH)₂ (Magnesium hydroxide)

Remember that some species can fall into multiple categories. For example, OH⁻ is both a strong nucleophile and a strong base[1][2]. Additionally, some strong bases like t-BuO⁻ are poor nucleophiles due to steric hindrance[4].