Remove- Ic Acid and Add -Yl Chloride) O

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Chapter 22 Naming Acid hadides (Remove- ic acid and add -yl chloride) O Cl acetyl chloride or ethanoyl chloride (see also benzoyl chloride) Anhydrides Symmetrical (Remove acid and add ahydride) O O O Acetic anhydride or ethanoic anhydride Mixed Anhydride (Use both acid names, out in alphabetical order) O O O Acetic benzoic anhydride or Benzoic ethanoic anhydride Esters (The acid part becomes the root. Remove- ic acid and use –ate as the ending. The alkyl group on the oxygen becomes the first part of the name.) O Cl O O O Ethyl Acetate 2-Chloroethyl benzoate Amides (Remove- ic acid, oic acid or ylic acid and add -amide) O N N-ethyl-N-methylbenzamide Nitriles ( Use alyl name and add nitrile or remove- ic acid and add-onitrile) N C N C H C Benzonitrile 3 Acetonitile (ethanenitrile) Lactones and Lactams & other strange examples O O O NH 4-Butanolactone or γ-Butyrolactone 4-Butanolactam or γ-Butyrolactam O OEt EtO O Diethylsuccinate O O O NH O sucinnic anhydride O succinamide Reactions of acids halides. Preparation O O SOCl2 OH Cl Sample Mechanism: Acetyl chloride plus dimethyl amine. O O 2 eq. (CH3)2NH CH N 3 Cl H C 3 CH N 3 H C 3 H O : O : Cl Cl H C H C + 3 3 N N H3C H CH3 .. CH NH 3 Other acid halide reactions: O O CH 3 OMe O OH H2O Me2CuLi MeOH (pyr) (pyr) O OH O CH3 Li(tBuO)3AlH H CH3 1. 2eq MeMgBr Cl + O 2. H3O wkup Et2NH O O O (2 eq) O 2 eq NH3 O O NEt2 NH2 +NH Cl 4 Anhydrides Made from the acid chloride. Reacts in a similar way to the acid halide. A cyclic anhydride can be made from the diacid. O O OH heat O OH O O O O O H2O OH O pyridine O O O CH3OH OMe O pyridine O O O CH3NH2 (2 eq) NHCH3 O Carboxyllic acids O CH3OH O OH H2SO4 OMe O 1. NH3 O OH 2. heat NH2 O CH3NH2 O OH DCC NHCH 3 see mechanism on page 803 Fisher esterification/transesterification mechanism. H+ O CH3OH O OH H2SO4 OMe :OH2 H + O OMe H .. H H + O : O O + H O OH OH H .. + O O H C H C H 3 CH3OH 3 CH3OH H O OH O H H3C + H C O H 3 Esters O O HO OH O H H+, H O 2 OH H O 1. LiAlH 4 + + H , H2O 2. H , H2O wkup - OH , H2O O 1. CH3Li O HO 2. H+, H O O HO 2 OCH CH wkup 2 3 H+ CH3 CH3 NH3 CH3NH2 1. EtMgBr O 2. H+, H O 2 NH wkup 2 O HO Et NHCH3 Et Amides 1. LiAlH 4 O 2. H+, H O + H2N 2 O H , H O H 2 wkup OH + + NH4 H NH2 DIBAL-H 2. water OH-, H O O 2 H O O H+, H O 2 OH O O CH3 1. CH3MgBr 2. water 1. LiAlH 4 O 2. H+, H O + H2N 2 H , H O H N 2 wkup C OH H goes through amide DIBAL-H OH-, H O 2. water 2 O O O H H+, H O 2 OH O goes through amide Acid catalyzed hydrolysis of a nitrile (Compare to the base catalyzed hydrolysis on page 818.) H+ :NH3 O H2O H H3C C N + H+ O H O O H O + H C C N 3 H N H H H O H H2O + N H H O H H H N + H N H + H O + O O H O N H N H + H H H O H H H O H 2 .

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Acetic Anhydride
ACETIC ANHYDRIDE Method number: 102 Matrix: Air Target concentration: 5 ppm (20 mg/m3) OSHA PEL: 5 ppm (20 mg/m3) TWA ACGIH TLV: 5 ppm (20 mg/m3) ceiling Procedure: Samples are collected open face on glass fiber filters coated with veratrylamine and di-n-octyl phthalate. Samples are extracted with 50/50 (v/v) 2-propanol/toluene and analyzed by GC using a nitrogen- phosphorus detector (NPD). Recommended air volume and sampling rate: 7.5 L at 0.5 L/min ceiling 7.5 L at 0.05 L/min TWA Reliable quantitation limit: 0.094 ppm (0.39 mg/m3) Standard error of estimate at the target concentration: 6.4% Special caution: Ketene and acetyl chloride produce the same derivative as acetic anhydride. Coated filters should be used within a month of preparation. Status of method: Evaluated method. This method has been subjected to the established evaluation procedures of the Organic Methods Evaluation Branch. Date: October 1993 Chemist: Yihlin Chan Organic Methods Evaluation Branch OSHA Salt Lake Technical Center Salt Lake City, UT 84165-0200 1. General Discussion 1.1 Background 1.1.1 History In OSHA Method 82, acetic anhydride is collected on a glass fiber filter impregnated with 1-(2-pyridyl)piperazine, which reacts with the anhydride to form a derivative (Ref. 5.1). Attempts at using 1-(2-pyridyl)piperazine for the derivatization of maleic, phthalic, and trimellitic anhydrides failed, however, because the resulting derivatives of these anhydrides were found to be unstable. These anhydrides were derivatized with veratrylamine instead (Refs. 5.2-5.4).
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Title the Reaction of Methyl Chloride with Carbon Monoxide Author(S
Title The reaction of methyl chloride with carbon monoxide Author(s) Osugi, Jiro; Mizukami, Tetuo Citation The Review of Physical Chemistry of Japan (1964), 34(1): 7-18 Issue Date 1964-11-05 URL http://hdl.handle.net/2433/46843 Right Type Departmental Bulletin Paper Textversion publisher Kyoto University The Review of Physical Chemistry of Japan Vol. 34 No. 1 (1964) TftE REVIEW OF PHYSICAL CHE'HISTRY OF IAPA~, VDL. 34, No. 1, 1964 THE REACTION OF METHYL CHLORIDE WITH CARBON MONOXIDE BY ]IRD ~stlf,l ANDTETUO IVIIEUI:A]II* The reaction of methyl chloride witb carbon monoxide in the presence of pumice•anhydrous sodium borate catalyst yields mainly hydrogen chloride, methane, acetyl chloride and phosgene, and deposits carbon. Moreover, hydro• gen, methylene chloride, ethyl chloride and ethylene dichloride are obtained in a trace. From [he stand point of chemical kinetics the reaction is studied. From the initial rates of the products, the values of 13.1, I8.5, 23.2 and 27.Okcal/mole are obtained as the apparent activation energies {or the formation of acetyl chloride, phosgene, hydrogen chloride and methane respectively. Furthermore, the rates of formation of acetyl chloride and pbosgene are discussed. From the apparent rate constants, the apparent activation energies are obtained. The values are 19.0 kcal/male for acetyl chloride and 17.6 kcal/mole for phosgene. The reaction mechanism is discussed. Introduction Since a few years ago, carhop monoxide has been considered as one of the important materials for organic chemical industry, so there are some utilizations, such as s}•nthetic petroleum, Reppe's carhoxy- Iation reaction and oxo reaction etc.
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Prohibited and Restricted Chemical List
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Process for Preparing a Stabilized Chromium \III\ Propionate Solution
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United States Patent (19) 11 Patent Number: 5,672,749
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Chem263 Nov 25 Notes 2010
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