Are both of the glutamic acid’s carboxylic acid groups more acidic (i.e., have lower pKa’s) or...

Are both of the glutamic acid’s carboxylic acid groups more acidic (i.e., have lower pKa’s) or more basic (i.e., have higher pKa’s) than acetic acid’s carboxylic acid? (b) Which of glutamic acid’s two carboxylic acid groups, the side chain –COOH group on the left (named pKR) or the main chain –COOH group on the right (named pK1), has a pKa closer to that of acetic acid? Please explain you answer.

Expert Solution

a)

First, identify the values of the acids (COOH) present in the glutamic acid...

pKa1 = 2.19 pK2 = 4.25

For Acetic acid, pKa = 4.75

clearly, both are more acidic, this means that COOH groups in glutamic acid will be charged negatively before acetic acid'ds does.

b)

the one bonded to the side chain. Since it is far away, typically the Nitrogen/Oxygen interaciton on the main bond will make a very acidic group for the COOH (pKa1)

The side chain is actually pretty similar to acetic acid

R- CH2-CH2-COOH

recall that acetic acid is CH3-COOH

that is why the pKa of group 2 is similar to pka of acetic acid

queen_honey_blossom answered 2 years ago

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