1. Predict the products of the following reactions. In some cases it will be necessary to show the stable intermediates. 1. LDA diethyl malonate 2. n-PrBr . methyl 3-oxopentanoate 1. OMe, MeOH 2. benzoyl bromide 3. H₂0 A 1. base 2. benzoic anhydride 3. H30 A

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Chapter1: Chemical Foundations
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1. Predict the products of the following reactions. In some cases it will be necessary to show
the stable intermediates.
diethyl malonate
. methyl 3-oxopentanoate
OTS
+
diethyl malonate
1. LDA
2. n-PrBr
ethyl acetoacetate
diethyl malonate
NaCH(CO₂R)2
8⁰
1. base
2. benzoic anhydride
3. H₂0 A
1. OMe, MeOH
2. benzoyl bromide
3. H₂0, A
1.9OEt
2. isobutylene epoxide
CH2(CO,Me)
LiH (XS)
3. H30, A
1. (XS) NaOEt
2. Br(CH₂)4Br
3. H30, A
1. OET, HOEt
2. butanoyl chloride
3. H30, A
benzaldehyde + acetophenone
95%
1. OH, (-H₂O)
2. NaCH(CO₂R)2
3. H30Ⓡ
+CHO
OH
1. methyl vinyl ketone
2. H30Ⓡ
3. NaOH (aldol)
1. KOH, EtOH
2. Δ
2 CO₂
OEt, EtOH
(C7H12O)
+
91%
1. SOCI₂
2. Me,NH
3. m-chloroperbenzoic acid
cis-jasmone (a perfume)
Transcribed Image Text:1. Predict the products of the following reactions. In some cases it will be necessary to show the stable intermediates. diethyl malonate . methyl 3-oxopentanoate OTS + diethyl malonate 1. LDA 2. n-PrBr ethyl acetoacetate diethyl malonate NaCH(CO₂R)2 8⁰ 1. base 2. benzoic anhydride 3. H₂0 A 1. OMe, MeOH 2. benzoyl bromide 3. H₂0, A 1.9OEt 2. isobutylene epoxide CH2(CO,Me) LiH (XS) 3. H30, A 1. (XS) NaOEt 2. Br(CH₂)4Br 3. H30, A 1. OET, HOEt 2. butanoyl chloride 3. H30, A benzaldehyde + acetophenone 95% 1. OH, (-H₂O) 2. NaCH(CO₂R)2 3. H30Ⓡ +CHO OH 1. methyl vinyl ketone 2. H30Ⓡ 3. NaOH (aldol) 1. KOH, EtOH 2. Δ 2 CO₂ OEt, EtOH (C7H12O) + 91% 1. SOCI₂ 2. Me,NH 3. m-chloroperbenzoic acid cis-jasmone (a perfume)
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