第11題
Ha is an aliphatic proton; its pKa > 50
Hb's carbon is alpha to a carbonyl group; its pKa ~20
Hc's carbon is alpha to 2 carbonyl group; its pKa ~10
Hd and He are aromatic proton, 40 > pKa >30
第12題
The leaving group is ethoxide (-OEt).
第15題
It is a Friedel-Craft's acylation reaction.
The E+ (acyl cation) would NOT rearrange. (textbook p.290 paragraph 1)
Therefore Friedel-Craft's acylation followed by Wolff-Kishner
reduction is a useful rxn sequence to synthesize n-alkyl benzene
derivatives.
第16題_
The first two reaction conditions would give double methylated product.
From F, hydrolysis followed by decarboxylation would occur to
give product G.
第20題
EWG would increase electron deficiency of carbonyl's carbon and
make it a better electrophile.
第22題
For the last reaction, a tertiary chloride would undergo solvolysis
reaction (SN1-like) and generate a tertiary carbocation (and also a
benzylic carbocation) intermediate. Therefore, a EDG at para position
would stabilize the intermediate and give negative rho value.
第24題
You should note that the nitrogen atom on pyridinium ring is also a
chirality center.
You may replace either Ha or Hb with D. You would find that the
two deuterated NADHs are diastereomers.
有其他問題歡迎繼續討論
助教 楊雲欽
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