Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter13: Substitution
Section: Chapter Questions
Problem 29CTQ
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Question
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The second page is an example how it suppose to be done.
(Hex-4-en-3-one+CH3CH2MgBR). It's complete. Please follow directions.
![bb. acetyl chloride + 2 equivalents of methylamine
1. React the carbonyl compound:
It is (circle one) CONJUGATED
NON-CONJUGATED
The Nucleophile is
Potential to Establish a Resonance System
Option 1: Almost all reactions
Option 2: When Nu is a strong base (OH or OR),
1 (Preferred)
and the leaving group is identical to the Nu
(option 1 is react the electron-rich nucleophile
with the electron- deficient carbonyl carbon)
(option 2 is remove the alpha hydrogen and
create a resonance-stabilized carbanion that can
act as a nucleophile.)
Circle the option and reason for reacting with a
particular site of the carbonyl compound
Option 1: Always use UNLESS
Option 2: The Nu matches Y AND is -OR
2. Take care of the negative formal charge of the oxygen in the tetrahedral complex
Option 1 (Preferred): All cases except Option 2
1 (Preferred)
Option 2: If there are no leaving groups,
or if the only potential leaving group is
the Nu that was just added and it
is not a very good leaving group (N or O).
(option 1 is reform the double bond)
(option 2 is add a hydrogen ion)
Circle the option and reason
* if you reform the Double bond
Whats the
Reason?
Option 1: Always use UNLESS
- LeGuing group?
- Shells ?
- elec tronegativity?
Ew A/ Reasomaue?
charge ?
Option 2: There is no leaving group (there are
carbons and hydrogens), OR there are only
carbons and hydrogens except for the Nu that
just added, AND it is N or O.
3. Check to see if the reaction continues
(xs Nu, or C with 4 single bonds, 2 electron-withdrawing atoms with non-bonded electron pairs.)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8229ea5b-aafe-4a8a-8035-6fec5bb42fe1%2Fd4c75df3-546a-4530-8282-6db3ce3d6e54%2Fqzbqq_processed.jpeg&w=3840&q=75)
Transcribed Image Text:bb. acetyl chloride + 2 equivalents of methylamine
1. React the carbonyl compound:
It is (circle one) CONJUGATED
NON-CONJUGATED
The Nucleophile is
Potential to Establish a Resonance System
Option 1: Almost all reactions
Option 2: When Nu is a strong base (OH or OR),
1 (Preferred)
and the leaving group is identical to the Nu
(option 1 is react the electron-rich nucleophile
with the electron- deficient carbonyl carbon)
(option 2 is remove the alpha hydrogen and
create a resonance-stabilized carbanion that can
act as a nucleophile.)
Circle the option and reason for reacting with a
particular site of the carbonyl compound
Option 1: Always use UNLESS
Option 2: The Nu matches Y AND is -OR
2. Take care of the negative formal charge of the oxygen in the tetrahedral complex
Option 1 (Preferred): All cases except Option 2
1 (Preferred)
Option 2: If there are no leaving groups,
or if the only potential leaving group is
the Nu that was just added and it
is not a very good leaving group (N or O).
(option 1 is reform the double bond)
(option 2 is add a hydrogen ion)
Circle the option and reason
* if you reform the Double bond
Whats the
Reason?
Option 1: Always use UNLESS
- LeGuing group?
- Shells ?
- elec tronegativity?
Ew A/ Reasomaue?
charge ?
Option 2: There is no leaving group (there are
carbons and hydrogens), OR there are only
carbons and hydrogens except for the Nu that
just added, AND it is N or O.
3. Check to see if the reaction continues
(xs Nu, or C with 4 single bonds, 2 electron-withdrawing atoms with non-bonded electron pairs.)
![CH3 -CH 2CH=cH-CHz
z. hex-4-en-3-one + CH3CH2MgBr
1. React the carbonyl compound:
It is (circle one) CONJUGATED NON-CONJUGATED
CH- CH2
The Nucleophile is
CH3- CH
= ě - cH = CH;-CHts
Resonance System
Option 1: Only the Nu created
from RMgBr, NaBH or LIAIH, sticks
R
R-CH CH
8+
Option 2 All other Nu end up here eventually
1 (Preferred)
NUB
CHg-CH,
(option 1 is react the electron-rich nucleophile
with the electron- deficient carbonyl carbon)
(option 2 is to react the electron-rich nucleophile
with the slightly electron-deficient carbon at the
end of the resonance system.)
Circle the option and reason for reacting with a
particular site of the carbonyl compound
Option 1: RMgBr, LIAIH4, or NaBH4
Option 2: All other Nu end up sticking here
2. Take care of the negative formal charge of the oxygen in the tetrahedral complex
:0:a Ht
- CH-CH-CH3
CH2-CH3
Option 1 (Prefered). All cases except Option 2
1 (Preferred)
Option 2: If there are no leaving groups,
or if the only potential leaving group is
the Nu that was just added and it
is not a very good leaving group (N or O).
(option 1 is reform the double bond)
(option 2 is add a hydrogen ion)
Circle the option and reason
Option 1: Always use UNLESS
* if u reform the DOuble bond
you
Option 2: There is no leaving group (there are
whots tle
Reason?
carbons and hydrogens), OR there are only
carbons and hydrogens except for the Nu that
Ew A/ ReaSonae?
- LeGuing group?
- Shells ?
elec trinegativity?
just added, AND it is N or O.
|
charge
3. Check to see if the reaction continues (xs Nu, or C with 4 single bonds, 2 electron-withdrawing atoms with non-bonded electron
pairs.)](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2F8229ea5b-aafe-4a8a-8035-6fec5bb42fe1%2Fd4c75df3-546a-4530-8282-6db3ce3d6e54%2Ffl0p20l_processed.jpeg&w=3840&q=75)
Transcribed Image Text:CH3 -CH 2CH=cH-CHz
z. hex-4-en-3-one + CH3CH2MgBr
1. React the carbonyl compound:
It is (circle one) CONJUGATED NON-CONJUGATED
CH- CH2
The Nucleophile is
CH3- CH
= ě - cH = CH;-CHts
Resonance System
Option 1: Only the Nu created
from RMgBr, NaBH or LIAIH, sticks
R
R-CH CH
8+
Option 2 All other Nu end up here eventually
1 (Preferred)
NUB
CHg-CH,
(option 1 is react the electron-rich nucleophile
with the electron- deficient carbonyl carbon)
(option 2 is to react the electron-rich nucleophile
with the slightly electron-deficient carbon at the
end of the resonance system.)
Circle the option and reason for reacting with a
particular site of the carbonyl compound
Option 1: RMgBr, LIAIH4, or NaBH4
Option 2: All other Nu end up sticking here
2. Take care of the negative formal charge of the oxygen in the tetrahedral complex
:0:a Ht
- CH-CH-CH3
CH2-CH3
Option 1 (Prefered). All cases except Option 2
1 (Preferred)
Option 2: If there are no leaving groups,
or if the only potential leaving group is
the Nu that was just added and it
is not a very good leaving group (N or O).
(option 1 is reform the double bond)
(option 2 is add a hydrogen ion)
Circle the option and reason
Option 1: Always use UNLESS
* if u reform the DOuble bond
you
Option 2: There is no leaving group (there are
whots tle
Reason?
carbons and hydrogens), OR there are only
carbons and hydrogens except for the Nu that
Ew A/ ReaSonae?
- LeGuing group?
- Shells ?
elec trinegativity?
just added, AND it is N or O.
|
charge
3. Check to see if the reaction continues (xs Nu, or C with 4 single bonds, 2 electron-withdrawing atoms with non-bonded electron
pairs.)
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