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6. Haworth Synthesis Friedel Crafts FIRST Clemensen acylation Anhydrous AICI, A reduction CH2 +soCI, CH2 CH2 Zn[Hg), conc. HCI Wolff-Kishner Reduction NH,-NH, & KOH in ethane-1,2-diol 4-phenyl butanoic acid (1-phenyl butyric acid) benzene succinie 4-oxo-4-phenyl solvent butanoic acid (B-benzoyl propionic acid) Dehydration / Cyclization 4-phenyl butanoyl chloride (r-phenyl butyryl chloride) anhydride -Hat Conc H,SO, IPPA /P,0s/-H,0 HF I Conc H,PO, Friedel Crafts Intramolecular acylation Anhydrous AICI, I Sncl, A SECOND Clemensen Dehydrogenation / Oridation/ Aromatization Palladised Charcoal (Pd-C)/Selenium A reduction Zn(Hg),HCI Wolf-Kishner Reduction NH,-NH, & KOH in ethane-1,2-diol naphthalene 1.2,3,4-tetrahydro naphthalene (tetralin) 3,4-dihydro naphthalen-1(2H)-one (a-tetralone) solvent

6. Haworth Synthesis Friedel Crafts FIRST Clemensen acylation Anhydrous AICI, A reduction CH2 +soCI, CH2 CH2 Zn[Hg), conc. HCI Wolff-Kishner Reduction NH,-NH, & KOH in ethane-1,2-diol 4-phenyl butanoic acid (1-phenyl butyric acid) benzene succinie 4-oxo-4-phenyl solvent butanoic acid (B-benzoyl propionic acid) Dehydration / Cyclization 4-phenyl butanoyl chloride (r-phenyl butyryl chloride) anhydride -Hat Conc H,SO, IPPA /P,0s/-H,0 HF I Conc H,PO, Friedel Crafts Intramolecular acylation Anhydrous AICI, I Sncl, A SECOND Clemensen Dehydrogenation / Oridation/ Aromatization Palladised Charcoal (Pd-C)/Selenium A reduction Zn(Hg),HCI Wolf-Kishner Reduction NH,-NH, & KOH in ethane-1,2-diol naphthalene 1.2,3,4-tetrahydro naphthalene (tetralin) 3,4-dihydro naphthalen-1(2H)-one (a-tetralone) solvent

Chemistry
Chemistry
10th Edition
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
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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Make an electron-flow-mechanism for this synthetic scheme. This involves predicting major and by-products using electronic and structural effects. The arrow push mechanism must be shows. (BENZENE -> NAPHTHALENE)

6. Haworth Synthesis Friedel Crafts FIRST Clemensen acylation Anhydrous AICI, A reduction CH2 Zn(Hg), conc. HCI Wolf-Kishner CH2 CH2 +soci, -so, -HCit Reduction NH,-NH, & KOH in ethane-1,2-diol 4-oxo-4-phenyl solvent 4-phenyl butanoic acid 4-phenyl butanoyl chloride (r-phenyl butyryl chloride) benzene succinic anhydride butanoic acid (B-benzoyl (r-phenyl butyric acid) propionic acid) Dehydration / Cyclization Conc H,SO, IPPA / P,0;/-H,0 HF I Conc H,PO, -HCit Friedel Crafts intramolecular acylation Anhydrous AICI, I Sncl, A SECOND Clemensen reduction Dehydrogenation / Oxidation/ Aromatization Palladised Charcoal (Pd-C)/ Selenium A -2H, Zn(Hg).HCI Wolf-Kishner Reduction NH, NH, & KOH in ethane-1,2-diol naphthalene 1,2,3,4-tetrahydro naphthalene (tetralin) 3,4-dihydro naphthalen-1(2H)-one (a-tetralone) solvent
Transcribed Image Text:6. Haworth Synthesis Friedel Crafts FIRST Clemensen acylation Anhydrous AICI, A reduction CH2 Zn(Hg), conc. HCI Wolf-Kishner CH2 CH2 +soci, -so, -HCit Reduction NH,-NH, & KOH in ethane-1,2-diol 4-oxo-4-phenyl solvent 4-phenyl butanoic acid 4-phenyl butanoyl chloride (r-phenyl butyryl chloride) benzene succinic anhydride butanoic acid (B-benzoyl (r-phenyl butyric acid) propionic acid) Dehydration / Cyclization Conc H,SO, IPPA / P,0;/-H,0 HF I Conc H,PO, -HCit Friedel Crafts intramolecular acylation Anhydrous AICI, I Sncl, A SECOND Clemensen reduction Dehydrogenation / Oxidation/ Aromatization Palladised Charcoal (Pd-C)/ Selenium A -2H, Zn(Hg).HCI Wolf-Kishner Reduction NH, NH, & KOH in ethane-1,2-diol naphthalene 1,2,3,4-tetrahydro naphthalene (tetralin) 3,4-dihydro naphthalen-1(2H)-one (a-tetralone) solvent
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