Practice_Quiz_19_blank

Practice_Quiz_19_blank - with diethyl adipate? CO 2 Et CO 2...

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(A) C 6 H 5 CH 2 COOEt (i) NaOEt/EtOH heat (ii) workup C 18 H 18 O 3 (B) CH 3 CCH 3 O = + CH 3 CH 2 CO 2 Et (i) NaOEt/EtOH heat (ii) workup C 6 H 10 O 2 Practice Quiz 19 (1) Provide the missing structures inside the boxes below. (C) EtO 2 CCH 2 CO 2 Et (i) 1.0 Eq NaOEt/EtOH (ii) 1.0 eq (CH 3 ) 2 CHCH 2 CH 2 Br
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(2) Provide the missing structures in the synthetic sequence below. C 6 H 5 CO 2 Et + C 6 H 5 CH 2 CO 2 Et (i)1.0 eq NaOEt (i) KOH, H 2 O, heat (ii) H 3 O + , heat C 18 H 20 O ethanol 1.0 eq NaOEt ethanol CH 3 CH 2 CH 2 CH 2 Br (ii) H 3 O +
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(3) Answer the following questions. O = COOH CH 3 CH 2 CHCOOH COOH =O COOH CH 3 CH 2 CH 2 CCOOH O I II III IV only II II, III I, II II,III,IV (A) Which of the following carboxylic acids will decarboxylate with vigorous heating? (B) What is the order of base strength (strongest to weakest) among the following anions? CH 3 CH 2 O - - CH 2 COCH 2 CH 3 O CH 3 CCHCOCH 2 CH 3 O O - I II III I>II>III III>I>II II>I>III I>III>II (C) What is the product of the following synthetic sequence starting
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Unformatted text preview: with diethyl adipate? CO 2 Et CO 2 Et (i) NaOEt/EtOH (ii) C 6 H 5 CH 2 Br (i) dil NaOH/H 2 O (ii) vigorous heat = O CH 2 C 6 H 5 = O C 6 H 5 CH 2 CO 2 Et CH 2 C 6 H 5 O CH 2 C 6 H 5 (4) Sketch mechanisms for the first part of the synthesis described in (3)(C) above that involves ring closure and alkylation. CO 2 Et CO 2 Et (i) NaOEt/EtOH (ii) C 6 H 5 CH 2 Br = O CH 2 C 6 H 5 EtOOC (5) Draw resonance structures for the enol (I) and enamine (II) that explain the nucleophilic character of the -carbons. CH 3 C=CHCH 3 OH CH 3 C=CHCH 3 N(CH 3 ) 2 I II (6) Design two syntheses of 2-methylcyclohexanone from cyclohexanone using direct alkyation methods recently discussed. O = O CH 3...
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Practice_Quiz_19_blank - with diethyl adipate? CO 2 Et CO 2...

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