#11 Be sure to answer all parts.Ethyl butanoate, CH3CH₂CH₂CO₂CH₂CH3, is one of the many organic compounds isolated frommangoes. Which hydrogen is most readily removed when ethyl butanoate is treated with base?Propose a reason for your choice, and using the data listed below, estimate its pka.CompoundCH3CONH₂CH3CHO(CH3)3COH(CH3)2C=OCH3CO₂CH₂CH3HC=CHCH3C=NCHCI3CH3CON(CH3)2The most readily removed type of hydrogen is on the:CH₂ bonded to C=0.CH₂ of the ethyl group.CH3 of the ethyl group.CH3 of the propyl group.The estimated pK₂ ispka16171819.224.525252530This type of hydrogen is most readily removed because:The conjugate base is stabilized by resonance.The conjugate base is stabilized by inductance.Loss of the proton deceases steric hindrance around the C=O.The conjugate base is stabilized by the high electronegativity of O.

Given:Ethyl butanoate, CH3CH2CH2CO2CH2CH3, is one of the many organic compounds isolated from…

Ethyl butanoate, CH3CH₂CH₂CO₂CH₂CH3, is one of the many organic compounds isolated from mangoes. Which hydrogen is most readily removed when ethyl butanoate is treated with base? Propose a reason for your choice, and using the data listed below, estimate its pK₂.

Ethyl butanoate, CH3CH₂CH₂CO₂CH₂CH3, is one of the many organic compounds isolated from mangoes. Which hydrogen is most readily removed when ethyl butanoate is treated with base? Propose a reason for your choice, and using the data listed below, estimate its pK₂.

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

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#11

Be sure to answer all parts.
Ethyl butanoate, CH3CH₂CH₂CO₂CH₂CH3, is one of the many organic compounds isolated from
mangoes. Which hydrogen is most readily removed when ethyl butanoate is treated with base?
Propose a reason for your choice, and using the data listed below, estimate its pka.
Compound
CH3CONH₂
CH3CHO
(CH3)3COH
(CH3)2C=O
CH3CO₂CH₂CH3
HC=CH
CH3C=N
CHCI3
CH3CON(CH3)2
The most readily removed type of hydrogen is on the:
CH₂ bonded to C=0.
CH₂ of the ethyl group.
CH3 of the ethyl group.
CH3 of the propyl group.
The estimated pK₂ is
pka
16
17
18
19.2
24.5
25
25
25
30
This type of hydrogen is most readily removed because:
The conjugate base is stabilized by resonance.
The conjugate base is stabilized by inductance.
Loss of the proton deceases steric hindrance around the C=O.
The conjugate base is stabilized by the high electronegativity of O.

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Step 2: Removal of H from CH3 of propyl group

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Step 3: Removal of H from CH2 and CH3 of ethyl group

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Step 4: Removal of H from CH2 bonded to C=O

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Step 5: Determine pKa

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