EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
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Chapter 29.SE, Problem 22MP
Interpretation Introduction

Interpretation:

The pentose phosphate pathway for degrading sugars (see Problem 29-21) is the conversion of ribose 5-phosphate to glyceraldehyde 3-phosphate.

EBK <x-custom-btb-me data-me-id='1631' class='microExplainerHighlight'>ORGANIC CHEMISTRY</x-custom-btb-me>, Chapter 29.SE, Problem 22MP , additional homework tip  1

Concept introduction:

Reactions that make and break C-C-Bonds

Reactions that make and break carbon-carbon bonds form the basis of both degradative and biosynthetic metabolism.

The breakdown of glucose to CO2 involves give such cleavages where as its synthesis involves the reverse process such reactions, considered from the synthetic direction involve addition of a nucleophilic carbanion to an electrophilic carbon atom. The most common electrophilic carbon atoms in such reactions are the sp2 hybridized carbonyl atoms of aldehydes, ketones, etc. and CO2

EBK ORGANIC CHEMISTRY, Chapter 29.SE, Problem 22MP , additional homework tip  2

Stabilized carbanions must be generated to add to these electrophilic centres. Three examples are the aldol condensation (catalyzed eg by aldolase) claisen ester condensation (citrate synthase) and the decarboxylation of β-keto acids. (isocitrate dehydrogenase and fatly acid synthase).

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19.78 Write the products of the following sequences of reactions. Refer to your reaction road- maps to see how the combined reactions allow you to "navigate" between the different functional groups. Note that you will need your old Chapters 6-11 and Chapters 15-18 roadmaps along with your new Chapter 19 roadmap for these. (a) 1. BHS 2. H₂O₂ 3. H₂CrO4 4. SOCI₂ (b) 1. Cl₂/hv 2. KOLBU 3. H₂O, catalytic H₂SO4 4. H₂CrO4 Reaction Roadmap An alkene 5. EtOH 6.0.5 Equiv. NaOEt/EtOH 7. Mild H₂O An alkane 1.0 2. (CH3)₂S 3. H₂CrO (d) (c) 4. Excess EtOH, catalytic H₂SO OH 4. Mild H₂O* 5.0.5 Equiv. NaOEt/EtOH An alkene 6. Mild H₂O* A carboxylic acid 7. Mild H₂O* 1. SOC₁₂ 2. EtOH 3.0.5 Equiv. NaOEt/E:OH 5.1.0 Equiv. NaOEt 6. NH₂ (e) 1. 0.5 Equiv. NaOEt/EtOH 2. Mild H₂O* Br (f) i H An aldehyde 1. Catalytic NaOE/EtOH 2. H₂O*, heat 3. (CH,CH₂)₂Culi 4. Mild H₂O* 5.1.0 Equiv. LDA Br An ester 4. NaOH, H₂O 5. Mild H₂O* 6. Heat 7. MgBr 8. Mild H₂O* 7. Mild H₂O+

Chapter 29 Solutions

EBK ORGANIC CHEMISTRY

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