Draw the Lewis structure of azidomethane (CH₃N₃) [Show two important resonance structures.]

Predict the K_eq for the following acid–base reaction.

Which of the following phenoxides should be a stronger nucleophile?

Would you expect the following substitution reaction to proceed with inversion or racemization? Why?

Give an acceptable name for each amine.

(a)

Give an acceptable name for each amine.

(b)

Give an acceptable name for each amine.

(c)

Given the following names, draw the structure of the molecule.

c. (S)-2-methyloctan-4-amine

Label the amines shown as a 1° amine, 2° amine, 3° amine, or 4° ammonium ion.

a.

b.

c.

d.

Draw a constitutional isomer for C₄H₁₁N containing a 1° amine at a

(a) 1° carbon,

(b) 2° carbon, and

(c) 3° carbon.

We usually calculate K_eq for acid–base reactions using pK_a values.

(a) Derive an equation to calculate K_eq using pK_b values, then

(b) use it to calculate the equilibrium constant for the following reaction.

Which would you expect to be a stronger nucleophile, ethyl amine or diethyl amine? Why?

Predict the product of the following reactions.

(c)

Given the starting reactant, suggest a method for synthesizing the amine on the right.

(b)

The nitro group directs electrophilic aromatic substitution to the meta position. After reduction by hydrogenation, to which carbon(s) does it direct?

Following a LiAlH₄ reduction, an IR spectrum suggested that the product was a mixture of the starting amide and the desired amine.

(b) Once separated, how could you distinguish between the amide and the amine using IR spectroscopy?

Given the pK_b, calculate the pK_a of the conjugate acid.

(b)

Given the pK_b, calculate the pK_a of the conjugate acid.

(c)

Calculate the equilibrium constant for each of the acid–base reactions shown.

b.

Despite the amino group being an ortho/para director, nitration of aniline gives the meta isomer predominantly. Explain this result.

Predict the product(s) of the reactions shown.

(b)

Predict the product(s) of the reactions shown.

(i)

Predict the product(s) of the reactions shown.

(j)

Suggest reagents to carry out the following transformations. Some may require more than one step.

(b)

The Gabriel synthesis is most frequently done with 1° alkyl halides. Why is it less successful with more substituted halides?

The final step in the synthesis of diazoxide, a drug used to treat low blood pressure, is shown here. Suggest a mechanism for this step.

The synthesis of ⍺-hydroxy acids can be done starting with amino acids. Suggest a mechanism of the two-step transformation shown. [The alcohol oxygen is the same in the reactant and product.