dd. cyclohexanone + 2 equivalents of ethanol 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 (Preforred) 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 reform the Double bond you the whats Reason? Option 1: Always use UNLESS EwA/ REASonae? ouing group? hells ? lec trinegativity? Option 2: There is no leaving group (there are carbons and hydrogens), OR there are only - charge . 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.)

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dd. cyclohexanone + 2 equivalents of ethanol
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,
R
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
Whots tle
Reason?
Option 1: Always use UNLESS
- LeGuing group?
- Shells ?
elec tranegativity?
Option 2: There is no leaving group (there are
charge ?
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.)
Transcribed Image Text:dd. cyclohexanone + 2 equivalents of ethanol 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, R 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 Whots tle Reason? Option 1: Always use UNLESS - LeGuing group? - Shells ? elec tranegativity? Option 2: There is no leaving group (there are charge ? 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.)
z. hex-4-en-3-one + CH3CH2MBBR
1. React the carbonyl compound:
It is (circle one) CONJUGATED
NON-CONJUGATED
CH3 - CH2
The Nucleophile is
CH, - CH - ĕ - CH = CH;-Clls
- CH =CH;-CH3
Resonance System
Option 1: Only the Nu created
from RMgBr, NaBH , or LIAIH, sticks
CH3-CH E- CH=cH-CH3
R-
CH CH
FR
Option 2: All other Nu end up here eventually
1 (Preferred)
NUB
CH3-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
Option 1 (Preferred): All cases except Option 2
:0:7Ht
CHe-(- CH -CH-CH3
CH2-CH3
1 (Preferred)
Option 2: If there are no leaving groups,
R.
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
you reform the
DOuble bond
Option 2: There is no leaving group (there are
carbons and hydrogens), OR there are only
whats
the
Reason?
EWA/ ReASonae?
carbons and hydrogens except for the Nu that
just added, AND it is N or O.
- Leauing group?
- Shells ?
- electronegativity?
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.)
Transcribed Image Text:z. hex-4-en-3-one + CH3CH2MBBR 1. React the carbonyl compound: It is (circle one) CONJUGATED NON-CONJUGATED CH3 - CH2 The Nucleophile is CH, - CH - ĕ - CH = CH;-Clls - CH =CH;-CH3 Resonance System Option 1: Only the Nu created from RMgBr, NaBH , or LIAIH, sticks CH3-CH E- CH=cH-CH3 R- CH CH FR Option 2: All other Nu end up here eventually 1 (Preferred) NUB CH3-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 Option 1 (Preferred): All cases except Option 2 :0:7Ht CHe-(- CH -CH-CH3 CH2-CH3 1 (Preferred) Option 2: If there are no leaving groups, R. 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 you reform the DOuble bond Option 2: There is no leaving group (there are carbons and hydrogens), OR there are only whats the Reason? EWA/ ReASonae? carbons and hydrogens except for the Nu that just added, AND it is N or O. - Leauing group? - Shells ? - electronegativity? 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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