aund= ney, churge Na O NH2 attack Tonic c) CH3CH2CH2CH,Li + NH3 (acid CH 3 CH2 CH2-CHz t WH2 (Conj acud) (base) (ca bu 2. The equilibrium idea means that if the reaction is reversible there will be four species in solution at one time, the acid, the base, the conjugate acid, and the conjugate base. Sometimes this is what is required, but at other times we need to choose bases that will completely deprotonate every molecule of acid, i.e. send the reaction completely to the right. These bases will include CH3CH,CH2CH;Li, NaNH2, and LiN(i-Pr)2. Weaker bases will include NaOH, NAOCH3, KOtBu, and NaOCH2CH3. For each of these bases, give the products formed when they react with H2O, then use pKa values to get an idea of the relative base strengths of these compounds. You will provided 7 separate reactions. 3. In CHEM 3112, we will study reactions based on the deprotonation of ketones such as acetone, (CH3)2C=0, which has a pKa of 19. Given the bases LiN(i-Pr)2 and NaOCH3, decide which one will be useful to completely deprotonate acetone, and which one will be useful for setting up an equilibrium. Explain your choices.

Introduction to General, Organic and Biochemistry
11th Edition
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Chapter7: Reaction Rates And Chemical Equilibrium
Section: Chapter Questions
Problem 7.81P
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aund=
ney, churge
Na O NH2
attack
Tonic
c) CH3CH2CH2CH,Li + NH3
(acid
CH 3 CH2 CH2-CHz t WH2
(Conj acud)
(base)
(ca bu
2. The equilibrium idea means that if the reaction is reversible there will be four species in solution at one time,
the acid, the base, the conjugate acid, and the conjugate base. Sometimes this is what is required, but at other
times we need to choose bases that will completely deprotonate every molecule of acid, i.e. send the reaction
completely to the right. These bases will include CH3CH,CH2CH;Li, NaNH2, and LiN(i-Pr)2. Weaker bases will
include NaOH, NAOCH3, KOtBu, and NaOCH2CH3. For each of these bases, give the products formed when
they react with H2O, then use pKa values to get an idea of the relative base strengths of these compounds.
You will provided 7 separate reactions.
3. In CHEM 3112, we will study reactions based on the deprotonation of ketones such as acetone, (CH3)2C=0,
which has a pKa of 19. Given the bases LiN(i-Pr)2 and NaOCH3, decide which one will be useful to completely
deprotonate acetone, and which one will be useful for setting up an equilibrium. Explain your choices.
Transcribed Image Text:aund= ney, churge Na O NH2 attack Tonic c) CH3CH2CH2CH,Li + NH3 (acid CH 3 CH2 CH2-CHz t WH2 (Conj acud) (base) (ca bu 2. The equilibrium idea means that if the reaction is reversible there will be four species in solution at one time, the acid, the base, the conjugate acid, and the conjugate base. Sometimes this is what is required, but at other times we need to choose bases that will completely deprotonate every molecule of acid, i.e. send the reaction completely to the right. These bases will include CH3CH,CH2CH;Li, NaNH2, and LiN(i-Pr)2. Weaker bases will include NaOH, NAOCH3, KOtBu, and NaOCH2CH3. For each of these bases, give the products formed when they react with H2O, then use pKa values to get an idea of the relative base strengths of these compounds. You will provided 7 separate reactions. 3. In CHEM 3112, we will study reactions based on the deprotonation of ketones such as acetone, (CH3)2C=0, which has a pKa of 19. Given the bases LiN(i-Pr)2 and NaOCH3, decide which one will be useful to completely deprotonate acetone, and which one will be useful for setting up an equilibrium. Explain your choices.
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