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™
Reactions of Ethers
Ethers (R-O-R’) are compounds formed by replacing hydrogen atoms of an alcohol (R-OH compound) or a phenol (C6H5OH) by an aryl/ acyl group (functional group after removing single hydrogen from an aromatic ring). In this section, reaction, preparation and behavior of ethers are discussed in the context of organic chemistry.
Epoxides
Epoxides are a special class of cyclic ethers which are an important functional group in organic chemistry and generate reactive centers due to their unusual high reactivity. Due to their high reactivity, epoxides are considered to be toxic and mutagenic.
Williamson Ether Synthesis
An organic reaction in which an organohalide and a deprotonated alcohol forms ether is known as Williamson ether synthesis. Alexander Williamson developed the Williamson ether synthesis in 1850. The formation of ether in this synthesis is an SN2 reaction.
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™](/v2/_next/image?url=https%3A%2F%2Fcontent.bartleby.com%2Fqna-images%2Fquestion%2Fcb45a7b7-d1aa-4ac7-ad98-90aa0325071f%2Fe45a9709-29f1-4b49-98ee-e31e2fa4b905%2Fmgu4nls_processed.png&w=3840&q=75)


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