Recognizing Strong/Weak Nucleophiles/bases

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Last updated 5:15 PM on 12/7/24
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23 Terms

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I⁻ (Iodide ion)

A strong nucleophile.

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HS⁻ (Hydrosulfide ion)

A strong nucleophile.

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RS⁻ (Thiolate ion)

A strong nucleophile.

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CN⁻ (Cyanide ion)

A strong nucleophile.

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N₃⁻ (Azide ion)

A strong nucleophile.

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OH⁻ (Hydroxide ion)

A strong base.

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RO⁻ (Alkoxide ion, e.g., CH₃O⁻)

A strong base.

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NH₂⁻ (Amide ion)

A strong base.

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LiAlH₄ (Lithium aluminum hydride)

A strong base.

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NaH (Sodium hydride)

A strong base.

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t-BuO⁻ (tert-Butoxide ion)

A bulky base.

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LDA (Lithium diisopropylamide)

A bulky base.

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

A bulky base.

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H₂O (Water)

A weak nucleophile.

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ROH (Alcohols)

A weak nucleophile.

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RCOOH (Carboxylic acids)

A weak nucleophile.

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NH₃ (Ammonia)

A weak base.

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C₅H₅N (Pyridine)

A weak base.

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CH₃NH₂ (Methylamine)

A weak base.

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NaHCO₃ (Sodium bicarbonate)

A weak base.

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Mg(OH)₂ (Magnesium hydroxide)

A weak base.

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What characterizes OH⁻ in terms of nucleophilicity and basicity?

It is both a strong nucleophile and a strong base.

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Why are some strong bases like t-BuO⁻ considered poor nucleophiles?

Due to steric hindrance.