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Chapter 23: Q13 P (page 1085)

Which compound is more easily decarboxylated?

Short Answer

Expert verified

Compound 2 is much easier to decarboxylate than compound 1 because of resonance.

Step by step solution

01

Resonance

Resonance is the phenomenon of delocalization of pi-electron in a structure. Resonance provides more stability to a molecule.

02

Stability of compound 1

The first compoundis given below here it can be seen that on elimination the electron left behind are not present in resonance and are localized on carbon which is less electronegative atom and hence this makes the decarboxylation difficult to occur

Compound 1

03

Stability of compound 2

The second compoundis given below here it can be seen that on elimination the electron left behind are delocalized to positively charged nitrogen in ring by resonance and nitrogen is highly electronegative atom and hence this makes the decarboxylation easy to occur.

Compound 2

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Most popular questions from this chapter

Question:Five coenzymes are required by -ketoglutarate dehydrogenase, the enzyme in the citric acid cycle that converts -ketoglutarate to succinyl-CoA.

a. Identify the coenzymes.

b.Propose a mechanism for the reaction.

Question:The glycine cleavage system is a group of four enzymes that together catalyze the following reaction:

glycine+THF鈫�glycinecleavagesystemN5,N10-methylene-THF+CO2

Use the following information to determine the sequence of reactions carried out by the glycine cleavage system:

a. The first enzyme is a PLP-requiring decarboxylase.

b. The second enzyme is aminomethyltransferase. This enzyme has a lipoate coenzyme.

c. The third enzyme synthesizes N6,N10-methylene-THF and also forms NH4

d. The fourth enzyme is an FAD-requiring enzyme.

e.The cleavage system also requires NAD.

Question: For each of the following reactions, name both the enzyme that catalyzes the reaction and the required coenzyme:

Explain why the hydrogens of the C-8 methyl group are more acidic than those of the C-7 methyl group.

Explain why the ability of PLP to catalyze an amino acid transformation is greatly reduced if the OH substituent of pyridoxal phosphate is replaced by OCH3.
See all solutions

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