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(c) With reference to the following reaction scheme: Me Mé N Boc 20 OMe DIBAL, toluene, -78 °C then H30Ⓡ w/up Me- Mé N Boc 21 H Useful structure: DIBAL= H. AI (i) Provide a curved arrow mechanism for the reduction of ester 20 to aldehyde 21. (ii) Explain why the reduction of ester 20 selectively affords aldehyde 21 in the of DIBAL, whereas treatment of 20 with LiAlH4 leads to over-reduction. presence

(c) With reference to the following reaction scheme: Me Mé N Boc 20 OMe DIBAL, toluene, -78 °C then H30Ⓡ w/up Me- Mé N Boc 21 H Useful structure: DIBAL= H. AI (i) Provide a curved arrow mechanism for the reduction of ester 20 to aldehyde 21. (ii) Explain why the reduction of ester 20 selectively affords aldehyde 21 in the of DIBAL, whereas treatment of 20 with LiAlH4 leads to over-reduction. presence

Chemistry
Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
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Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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(c) With reference to the following reaction scheme: Met N Me Boc 20 OMe DIBAL, toluene, -78 °C then H₂O w/up Me+N Mé Boc 21 H Useful structure: DIBAL= H₂ Al Y Bary (i) Provide a curved arrow mechanism for the reduction of ester 20 to aldehyde 21. (ii) Explain why the reduction of ester 20 selectively affords aldehyde 21 in the presence of DIBAL, whereas treatment of 20 with LiAlH4 leads to over-reduction.
Transcribed Image Text:(c) With reference to the following reaction scheme: Met N Me Boc 20 OMe DIBAL, toluene, -78 °C then H₂O w/up Me+N Mé Boc 21 H Useful structure: DIBAL= H₂ Al Y Bary (i) Provide a curved arrow mechanism for the reduction of ester 20 to aldehyde 21. (ii) Explain why the reduction of ester 20 selectively affords aldehyde 21 in the presence of DIBAL, whereas treatment of 20 with LiAlH4 leads to over-reduction.
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