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Chapter 17: Q3P (page 804)

Explain why a base can remove a proton from the α-carbon of N,N-dimethylethanamide but not from the -carbon of either N-methylethanamide or ethanamide.

N,N-dimethylethanamideN-methylethanamide Ethanamide

Short Answer

Expert verified

Due to the lack of N-H bond in N, N-dimethyl ethanamide, a base can remove a proton from the alpha carbon of N, N-dimethyl ethanamine.

Step by step solution

01

Acidic hydrogens

Hydrogen bonded to an α-carbon is more acidic than hydrogens bonded to other sp3 carbons because the base formed when a proton is removed from anα-carbon is relatively stable. And, as we have seen, the more stable the base, the stronger it’s the conjugate acid.

02

Removal of a proton by a base

The nitrogen atom is much more electronegative than carbon, nitrogen accepts a negative charge. Hence, the base can remove protons of nitrogen from N-methyl ethanamide and ethanamide.

Removal of proton

Whereas due to the lack of N-H bond in N, N-dimethyl ethanamide, a base can remove a proton from the alpha carbon of N, N-dimethyl ethanamine. The formed carbanion is a resonance stabilized anion.

Removal of proton

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Most popular questions from this chapter

Draw the products of the following reactions:

a. diethyl heptanedioate: (1) sodium ethoxide; (2) HCl

b. pentanoic acid + PBr3 + Br2, followed by hydrolysis

c. acetone + LDA/THF: (1) slow addition of ethyl acetate; (2) HCl

d. diethyl 2-ethylhexanedioate: (1) sodium ethoxide; (2) HCl

e. diethyl malonate: (1) sodium ethoxide; (2) isobutyl bromide; (3) HCl, H2O + ∆

f. acetophenone + LDA/THF: (1) slow addition of diethyl carbonate; (2) HCl

There are other condensation reactions similar to the aldol and claisen condensations:

a. The Perkin condensation is the condensation of an aromatic aldehyde and acetic anhydride. Draw the product obtained from the following Perkin condensation:

b. What compound is formed if water is added to the product of a Perkin condensation?

c. The Knoevenagel condensation is the condensation of an aldehyde or a ketone that has no alpha- hydrogens and a compound such as diethyl malonate that has an alpha-carbon flanked by two electron- withdrawing groups. Draw the product obtained from the following Knoevenagel condensation:

d. What product is obtained when the product of a Knoevenagel condensation is heated in an aqueous acidic solution?

Do a retrosynthetic analysis on each of the following compounds, ending with available starting materials.

(a)

(b)

(C)

(D)

(e)

Propose a mechanism for the formation of fructose-1, 6-bisphosphate from dihydroxyacetone phosphate and glyceraldehyde-3-phosphate, using hydroxide ion as the catalyst.

Show how the following compounds can be prepared from cyclohexanone:
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