By Trost B.M., Fleming I., Pattenden G. (eds.)
Quantity three covers carbon-to-carbon unmarried bond forming reactions regarding sp 3, sp 2 and sp carbon facilities, yet purely these which don't contain additions to C-X &pgr;-bonds. the quantity first compares and contrasts the alkylation reactions of all kinds of sp 3 carbon nucleophiles and likewise covers vinyl and alkynyl carbanions. Following on from quantity 2, a separate part covers Friedel-Crafts alkylation reactions, that's complemented through discussions of polyene cyclizations and electrophilic transannular cyclizations in synthesis. Coupling reactions resulting in &agr;-bond formation, and regarding all kinds of mixtures of sp 3, sp 2 and sp carbon facilities are subsequent lined, together with these reactions in accordance with pinacol, acyloin and phenol oxidative coupling reactions, and in addition the Kolbe response. Rearrangement reactions, resulting in carbon-to-carbon &agr;-bond formation, are usually utilized in a smart demeanour in synthesis. the amount contains all these rearrangement reactions in keeping with intermediate carbonium ions and carbanions, and likewise contains the benzil-benzilic acid and the Wolff rearrangements. the quantity closes with insurance of carbonylation reactions, and using carbene insertion reactions into the C-H bond in synthesis.
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Additional resources for Comprehensive Organic Synthesis: Carbon-Carbon sigma-Bond Formation
CH3)3O+ e. CH3 C C H 4 groups (3 atoms, 1 lone pair) sp3, tetrahedral d. CH2Cl 4 groups (4 atoms) sp3, tetrahedral 2 groups (2 atoms) sp, linear f. CH2=NOCH3 3 groups (2 atoms, 1 lone pair) sp2, trigonal planar g. CH3CH=C=CH2 3 groups (3 atoms) sp2 trigonal planar 2 groups (2 atoms) sp, linear Smith: Study Guide/ Solutions Manual to accompany Organic Chemistry, Third Edition 1. 29. O Csp2–Csp3 H H : Csp2–Osp2 : Cp–Op Csp3–H1s a. c. Csp3–Csp3 Csp–Csp2 : Csp2–Csp2 : Cp–Cp H Csp2–H1s b. H C C C N CH3 d.
CH3)2CHOH + Li+ –N[CH(CH3)2]2 acid base + HN[CH(CH3)2]2 conjugate base (CH3)2CHOH2 + conjugate acid conjugate acid –OCOCH 3 conjugate base To cross a cell membrane, amphetamine must be in its neutral (not ionic) form. CH3 CH2 CH3 protonation CH2 C H C H NH2 by HCl in the stomach NH2 CH3 deprotonation CH2 C H in the intestines H amphetamine NH2 absorption here in the neutral form Lewis bases are electron pair donors: they contain a lone pair or a bond. a. 29 propranolol OH Draw the products of proton transfer from the acid to the base.
Csp3–Csp3 Csp–Csp2 : Csp2–Csp2 : Cp–Cp H Csp2–H1s b. H C C C N CH3 d. 29. Csp3–Osp3 Osp3–H1s H a. : Csp2–Osp2 : Cp–Op O Csp3–Osp3 CO2H O O O b. 73 CH2 CH sp2 sp : Csp2–Csp : Cp–Cp CH2 CH sp2 sp2 : Csp2–Csp2 : Cp–Cp C 27 28 Smith: Study Guide/ 1. 34. H H a. C C H C C H H H H C C CH2 C C C H H H H H double bond middle triple bond shortest b. 34. a. HO NH2 b. ) Cl Br c. 76 c. shortest, strongest C–C bond b. and d. bond (1) longest, weakest C–C bond (2) single bond H a. shortest C–C single bond e.
Comprehensive Organic Synthesis: Carbon-Carbon sigma-Bond Formation by Trost B.M., Fleming I., Pattenden G. (eds.)