Synthesize (Z)-hept-5-en-2-one from ethyl acetoacetate (CH3COCH₂CO₂Et) and the given starting material. Br (z)-hept-5-en-2-one Draw four organic reaction intermediates, and select the single best set of reagents for each of the six reaction steps. CH3COCH₂CO₂Et draw structure ... draw structure ... O [1] NaOEt, [2] HC=CCH₂Br [1] HCI, [2] HC=CCH₂Br [1] Mg, [2] HC=CCH₂Br [1] H₂O, Cl₂, [2] HC=CCH₂Br 0000 O O H₂SO4 OH₂0¹, A OOO OOOO H₂ (2 equiv), Pd-C OOOO mCPBA HOCH2CH2OH, TSOH [1] LDA, THF; [2] BrCH₂CH₂Br OLIAIH4 KMnO4, H₂O, HO™ [1] NaH; [2] CH ₂1 H₂O, Br₂ H₂O, NaOH KMnO4, H₂O, HO™

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...
icon
Related questions
icon
Concept explainers
Question

HW9 #14

Be sure to answer all parts.
Synthesize
material.
(Z)-hept-5-en-2-one from ethyl acetoacetate (CH3COCH₂CO₂Et) and the given starting
Br
CH3COCH₂CO₂Et
Draw four organic reaction intermediates, and select the single best set of reagents for each of the six
reaction steps.
draw structure ...
draw structure ...
O
O O
OOOO
لد
OOOO
(z)-hept-5-en-2-one
H₂SO4
OH30¹, A
O O O O
[1] NaOEt, [2] HC=CCH₂Br
[1] HCI, [2] HC=CCH₂Br
[1] Mg, [2] HC=CCH₂Br
[1] H₂O, Cl₂, [2] HC=CCH₂Br
H₂ (2 equiv), Pd-C
mCPBA
HOCH₂CH₂OH, TSOH
[1] LDA, THF; [2] BrCH₂CH₂Br
OLIAIH4
OKMnO4, H₂O, HO™
[1] NaH; [2] CH₂I
H₂O, Br₂
H₂O, NaOH
KMnO4, H₂O, HO™
Transcribed Image Text:Be sure to answer all parts. Synthesize material. (Z)-hept-5-en-2-one from ethyl acetoacetate (CH3COCH₂CO₂Et) and the given starting Br CH3COCH₂CO₂Et Draw four organic reaction intermediates, and select the single best set of reagents for each of the six reaction steps. draw structure ... draw structure ... O O O OOOO لد OOOO (z)-hept-5-en-2-one H₂SO4 OH30¹, A O O O O [1] NaOEt, [2] HC=CCH₂Br [1] HCI, [2] HC=CCH₂Br [1] Mg, [2] HC=CCH₂Br [1] H₂O, Cl₂, [2] HC=CCH₂Br H₂ (2 equiv), Pd-C mCPBA HOCH₂CH₂OH, TSOH [1] LDA, THF; [2] BrCH₂CH₂Br OLIAIH4 OKMnO4, H₂O, HO™ [1] NaH; [2] CH₂I H₂O, Br₂ H₂O, NaOH KMnO4, H₂O, HO™
I
I
I
draw structure...
draw structure...
H₂, Lindlar catalyst
NaBH4
Na or Li, NH3
H₂, Pd-C
H3O+
HO™
H₂O
NaBH4
Transcribed Image Text:I I I draw structure... draw structure... H₂, Lindlar catalyst NaBH4 Na or Li, NH3 H₂, Pd-C H3O+ HO™ H₂O NaBH4
Expert Solution
trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 5 steps with 3 images

Blurred answer
Knowledge Booster
Ethers
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Chemistry
Chemistry
Chemistry
ISBN:
9781305957404
Author:
Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:
Cengage Learning
Chemistry
Chemistry
Chemistry
ISBN:
9781259911156
Author:
Raymond Chang Dr., Jason Overby Professor
Publisher:
McGraw-Hill Education
Principles of Instrumental Analysis
Principles of Instrumental Analysis
Chemistry
ISBN:
9781305577213
Author:
Douglas A. Skoog, F. James Holler, Stanley R. Crouch
Publisher:
Cengage Learning
Organic Chemistry
Organic Chemistry
Chemistry
ISBN:
9780078021558
Author:
Janice Gorzynski Smith Dr.
Publisher:
McGraw-Hill Education
Chemistry: Principles and Reactions
Chemistry: Principles and Reactions
Chemistry
ISBN:
9781305079373
Author:
William L. Masterton, Cecile N. Hurley
Publisher:
Cengage Learning
Elementary Principles of Chemical Processes, Bind…
Elementary Principles of Chemical Processes, Bind…
Chemistry
ISBN:
9781118431221
Author:
Richard M. Felder, Ronald W. Rousseau, Lisa G. Bullard
Publisher:
WILEY