Organic Chemistry

Problem # 304

Draw the conjugate base form of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

Explain your reasoning.

Solution

The ammonium species is the most acidic because its conjugate base is the most stable (because its neutral).

Neutral amines aren't acidic because their conjugate bases are very unstable- a nitrogen with a negative formal charge is a very strong base.

Problem Details

MendelSet practice problem # 304 submitted by Matt on June 7, 2011.

Subject: Organic Chemistry

Subject Topic(s): Acid Strength Trends and Conjugate Base Stability

Question Type: Concept (explain why this is so..)

Keyword(s): acid strength

Problem # 303

Draw the conjugate base form of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

Explain your reasoning.

Solution

Perchlorate (ClO₄^-) has the most resonance forms and therefore has the most electron delocalization, so it is the most stable and weakest base, which makes its conjugate acid (HClO₄) the strongest acid.

Problem Details

MendelSet practice problem # 303 submitted by Matt on June 7, 2011.

Subject: Organic Chemistry

Subject Topic(s): Acid Strength Trends and Conjugate Base Stability

Question Type: Concept (explain why this is so..)

Keyword(s): resonance, acid strength

Problem # 288

Draw the conjugate base form of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

Explain your reasoning.

Solution

Size increases as you go down the periodic table, so iodine is the larger than bromine, which is larger than chlorine, etc.

Because I^- is the largest anion, it is best able to "handle" its negative charge (due to its small charge:size ratio), and so is the most stable conjugate base, and therefore the weakest conjugate base. So HI is the strongest acid.

Problem Details

MendelSet practice problem # 288 submitted by Matt on June 6, 2011.

Subject: Organic Chemistry

Subject Topic(s): Acid Strength Trends and Conjugate Base Stability

Question Type: Concept (explain why this is so..)

Keyword(s): resonance, acid strength

Problem # 286

Draw the conjugate base forms of each acid listed below, then rank the acids in order or decreasing acidity (1 = most acidic).

Explain your reasoning.

Solution

Electronegativity increases as you travel from left to right along the periodic table, so the fluorine anion is more stable than a negative oxygen, which is more stable than a negative nitrogen, etc.

Because F^- is the most stable, it is the weakest base, and its conjugate acid (HF) is the most acidic.