Be sure to answer all parts. Synthesize the following compound from cyclohexanone and organic halides having ≤ 4 C's. You may use any other inorganic reagents. Draw all reaction intermediates, and select the single best set of reagents for each of the four reaction steps. Cyclohexanone draw structure... draw structure ... draw structure ... OOOO H₂O, Cl₂ (2 equiv) LDA, THF HCI NaBH4 draw structure ... Organic bromide having ≤4 C's LDA, THF --OCH3 LIAIH H₂SO4

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Chapter1: Chemical Foundations
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HW9 #13

Be sure to answer all parts.
Synthesize the following compound from cyclohexanone and organic halides having ≤4 C's. You may
use any other inorganic reagents.
Draw all reaction intermediates, and select the single best set of reagents for each of the four reaction
steps.
Cyclohexanone
draw structure ...
draw structure ...
draw structure ...
000
O O O O
H₂O, C1₂ (2 equiv)
LDA, THE
HCI
NaBH4
draw structure ...
Organic bromide
having ≤4 C's
LDA, THF
-OCH3
LIAIH4
H₂SO4
Transcribed Image Text:Be sure to answer all parts. Synthesize the following compound from cyclohexanone and organic halides having ≤4 C's. You may use any other inorganic reagents. Draw all reaction intermediates, and select the single best set of reagents for each of the four reaction steps. Cyclohexanone draw structure ... draw structure ... draw structure ... 000 O O O O H₂O, C1₂ (2 equiv) LDA, THE HCI NaBH4 draw structure ... Organic bromide having ≤4 C's LDA, THF -OCH3 LIAIH4 H₂SO4
draw structure ...
draw structure...
I
draw structure...
Organic bromide
having ≤4 C's
NaOCH3
O H₂O, Cl₂
Br2, CH₂COOH
H₂O, NaOH
Li₂CO3, LIBr, DMF
KMnO4, H₂O, HO™
LDA, THE
O Br₂, CH₂COOH
Transcribed Image Text:draw structure ... draw structure... I draw structure... Organic bromide having ≤4 C's NaOCH3 O H₂O, Cl₂ Br2, CH₂COOH H₂O, NaOH Li₂CO3, LIBr, DMF KMnO4, H₂O, HO™ LDA, THE O Br₂, CH₂COOH
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