20 Questions
What is a characteristic of the nitrogen atom in the rightmost resonance form of an amine?
It has a positive charge
What is the result of the Hofmann elimination reaction?
Elimination of H2O and formation of an alkene
What is true about the smell of amines?
Low molecular weight amines smell fishy, while larger diamines smell rotten
What is the geometry of the nitrogen atom in an amine?
Trigonal pyramidal
What is the result of the reduction of amides?
Conversion of C=O to CH2
What is the primary reason why amines with 5 or more C atoms are not fully soluble in water?
Presence of a larger hydrophobic part
Which of the following statements is true about the strength of amines as bases?
Amines with lower conjugate acid pKa values are stronger bases
What is the primary reason why amides are not good bases?
Presence of a second resonance form with a positive charge on the N atom
What reaction mechanism is used to delete the C=O group from an amide, forming an amine?
Hofmann rearrangement
Which of the following is not a method of preparing amines?
Hofmann elimination
What is the primary reason for the water solubility of amines with fewer than 5 carbons?
The formation of strong hydrogen bonds between the nitrogen atom and water
Which of the following classifications of amines has a nitrogen atom with a lone pair and three single bonds?
Quaternary ammonium salt
What is the relationship between the pKb value and the strength of a base in amines?
Low pKb value means a strong base
Why do small amines smell fishy?
The specific odor is a characteristic of small amines
What is the effect of electron-donating alkyl groups on the nitrogen atom in amines?
They make the nitrogen atom more electron-rich
What is the trend in the strength of the base as we go from NH3 to primary amine to secondary amine?
The strength of the base increases
Why is the tertiary amine a weaker base compared to primary and secondary amines?
Due to the decrease in solubility in water
What is the relation between pKa and pKb of a conjugate acid and base pair?
pKa + pKb = 14
What is the effect of the F atom on the basicity of the compound in the middle and rightmost compounds?
Decreases the basicity
Why do primary and secondary amines have approximately equal strengths as bases?
Due to their high solubility in water
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