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

Short Answer

Expert verified

The hydrogens of the C-8 methyl group are more acidic than those of the C-7 methyl group due to electron delocalization difference.

Step by step solution

01

Acidic hydrogen

The acidic hydrogen is the hydrogen atom that can be easily release from the compound and will make the solution acidic.

More the stability of conjugate base more easily proton is removed from molecule.

02

Proton removed from C-8 methyl group

In this case when the proton from methyl group at C-8 is removed then the electrons left are delocalized onto the oxygen at C-2 or C-4 position making the conjugate base more stable and hence the proton more acidic.

Proton removal from C-8 methyl group

03

Proton removed from C-7 methyl group

Here the electron left after proton removal are able to delocalize only on less electronegative atom that is carbon which have less ability to accommodate electron and hence making it less stable so hydrogen at C-7 methyl group are less acidic.

Proton removal from C-7 methyl group

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Most popular questions from this chapter

Question:When UMP is dissolved in T2O, exchange of T for H occurs at the 5-position. Propose a mechanism for this exchange.

Question: Answer the following:

a. What coenzyme transfers an acyl group from one substrate to another?

b. What is the function of FAD in the pyruvate dehydrogenase complex?

c. What is the function of NAD+ in the pyruvate dehydrogenase complex?

d. What reaction necessary for proper blood clotting is catalyzed by vitamin KH2?

e. What coenzymes are used for decarboxylation reactions?

f. What kinds of substrates do the decarboxylating coenzymes work on?

g. What coenzymes are used for carboxylation reactions?

h.What kinds of substrates do the carboxylating coenzymes work on?

Question: Name the coenzymes that

a. allow electrons to be delocalized.

b. are oxidizing agents.

c. provide a strong base.

d.donate one-carbon groups

a. What acyl group does pyruvate decarboxylase transfer to a proton?

b. What acyl group does the pyruvate dehydrogenase complex transfer to coenzyme A?

c. What acyl group does transketolase transfer to ribose-5-P?

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

glycine+THFglycinecleavagesystemN5,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.

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