phenyl groups, they already start with 18 C's - so Wittig reagents may have 20 total carbons, at most). a. Think Backwards: Imines come from ketones or aldehydes..... Need to build 2- butanone from two-carbon sources... O OH NH
phenyl groups, they already start with 18 C's - so Wittig reagents may have 20 total carbons, at most). a. Think Backwards: Imines come from ketones or aldehydes..... Need to build 2- butanone from two-carbon sources... O OH NH
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
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Question
Could you show the mechanism for Question 4, parts A-C?

Transcribed Image Text:phenyl groups, they already start with 18 C's - so Wittig reagents may have 20 total
carbons, at most).
a. Think Backwards: Imines come from ketones or aldehydes.... Need to build 2-
butanone from two-carbon sources...
MgBr
or
H
H H
PH3P=CHCH3
H
H
OH
e
MgBr
H
OH
1. BH3
2. NaOH,
H₂O₂
The alkene is symmetrical. Hydroboration, oxymercuration or acid-catalyzed hydration
all work for step two.
PCC
b. Enamines come from ketones or aldehydes. Need to add two carbons to both sides
of the ketone...
PCC
I
or in this version, just use a Wittig reagent...
O
OH
MgBr
OH
POCI 3
pyridine
PCC
PCC
X
c. Need to form 3-pentanone, then add two more carbons and institute the double
bond.... In this answer, we will dehydrate a symmetrical alcohol...
OH
MgBr
PCC
MgBr
OH
NH3
H*
MgBr
NH(CH3)2, H*
NH
I
MgBr
MgBr
Ph3P=CHCH3
NH3
H*
OH
PCC
OH
PCC
NH
çoğça fo
PCC

Transcribed Image Text:3. Construct the following compounds using only the following carbon sources and
whatever other inorganic reagents (oxidants, reducing agents, etc): formaldehyde,
acetaldehyde, acetone, 1-butanol.
a. 4 Carbons becoming 5 Carbons - Need to add one more carbon (must be using
formaldehyde)... Thinking backwards - Alcohols form from Grignards reacting with
aldehydes... Need to make a Grignard...
PBr3
H&H
OH
НО.
OH
Br
b. 4 Carbons becoming 6 Carbons - Need to add two more carbons (must be using
acetaldehyde). Thinking backwards - Chlorides come from alcohols, alcohols come from
Grignards with aldehydes... Need a four carbon Grignard...
PBr3
Mg
PBr3
Br
Mg
Br
MgBr
Mg
CI
c. 4 Carbons becoming 7 Carbons - Need to add three more carbons (must be using
acetone). Thinking backwards - Alkenes come from the dehydration of alcohols, alcohols
come from Grignards with ketones... Need a four carbon Grignard...
BrMg.
MgBr H
OH
OH
OH
SOCI₂,
pyridine
{d}
POCI3
pyridine
more than
4. For the following compounds, construct them from reagents containing no
two carbons (with the exception of any Wittig reagent you would like to use with three
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