Question

Starting from acetoacetic ester, list in order (by letter, no period), the given reagents required to synthesize each of the following.
Note: not all steps may be necessary. If a step is not needed, type 'na'.

HO MeOH, H2SO4 (1)ONa (2) Mel OH (2) Br НА OEt (1) LDA (2) CH3l (1) Mg (2) H3o (1) HO, H2O, heat (2) H3ot (2) Mel (1)︿ONa (1)

(a) tert-Butyl methyl ketone Step #1 Step #2 Step #3 Step #4 Step #5 Step #6 (b) 2-Hexanone Step #1 Step #2 Step #3 Step #4

(c) 2,5-Hexanedione Step #1 Step #2 Step #3 Step #4 (d) 4-Hydroxypentanoic acid Step #1 Step #2 Step #3 Step #4

(E) 2-Ethyl-1,3-butanediol Step #1 Step #2 Step #3 Step #4 (f) 1-Phenyl-1,3-butanediol Step #1 Step #2 Step #3 Step #4

HO MeOH, H2SO4 (1)ONa (2) Mel OH (2) Br НА OEt (1) LDA (2) CH3l (1) Mg (2) H3o (1) HO, H2O, heat (2) H3ot (2) Mel (1)︿ONa (1) NaH heat (2) CcH5、 .cl NaBH4 CO2 ()ONa (1 ) LiAlH4 (2) H3Ot 1ONa PBr3
(a) tert-Butyl methyl ketone Step #1 Step #2 Step #3 Step #4 Step #5 Step #6 (b) 2-Hexanone Step #1 Step #2 Step #3 Step #4
(c) 2,5-Hexanedione Step #1 Step #2 Step #3 Step #4 (d) 4-Hydroxypentanoic acid Step #1 Step #2 Step #3 Step #4
(E) 2-Ethyl-1,3-butanediol Step #1 Step #2 Step #3 Step #4 (f) 1-Phenyl-1,3-butanediol Step #1 Step #2 Step #3 Step #4
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OEE oEt oEt う 丁 01イ 6

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