Dimethyl-2-chloro-propanol

C5H10O2S 3-methyl sulfolane 872-93-5 549.15 52.851 1,2 5638 C5H11CIO 3-chloro-2,2-dimethyl-1-propanol 13401-56-4 418.07 36 071 2... 

O 18.58% liq, bp 79.5-80° obtd from 3-chloro-2,2-dimethyl-l-propanol by stirring with powd KOH in tert-amyl alcohol at 95°, and boiling at 48° to separate the oxetane (Ref 4)... 

Problem 17.47. Draw the stereoisomers, if any, of each of the following (a) 1,1-dimethyl-l-propanol, (b) 2-methyl-l-propanol, (c) 1-propanol, id) 1-methyl-1-propanol, (e) 3-chloro-2-butanol, (/) 2,3-butanediol. 

On prolonged heating with concentrated hydrochloric acid, 2,2-dimethyl-1-propanol, a primary alcohol, reacts to give 2-chloro-2-methylbutane. Provide a stepwise mechanism for this reaction, using curved arrows to symbolize the... 

For primary alcohols with extensive -branching, such as 2,2-dimethyl-l-propanol (neopentyl alcohol), it is difficult, if not impossible, for reaction to occur by direct displacement of H2O from the primary carbon. Furthermore, formation of a 1 ° car-bocation is also difficult, if not impossible. Instead, primary alcohols with extensive 8-branching react by a mechanism involving formation of a 3° carbocation intermediate by simultaneous loss of H2O and migration of an allgrl group, as illustrated by the conversion of 2,2-dimethyl-l-propanol to 2-chloro-2-methylbutane. Because the rate-determining step of this transformation involves only one reactant, namely the protonated alcohol, it is classified as an Sj. 1 reaction. 

Figure 12.12 THM GC/MS curves of a Winsor Newton lemon alkyd paint (a) and of an alkyd sample taken from Fontana s work Concetto spaziale (1961) (b). Peak assignments 1, 1,3 dimethoxy 2 propanol 2, 1,2,3 trimethoxy propane 3, 3 methoxy 1,2 propandiol 4, 4 chloro benzenamine 5, 3 methoxy 2,2 bis(methoxymethyl) 1 propanol 6, 3 chloro N methyl benzenamine 7, 3 methoxy 2 methoxymethyl 1 propanol 8, 4 chloro N methyl benzenamine 9, phthalic anhydride 10, 3 chloro 4 methoxy benzenamine 11, suberic acid dimethyl ester 12, dimethyl phthalate 13, azelaic acid dimethyl ester 14, sebacic acid dimethyl ester 15, palmitic acid methyl ester 16, oleic acid methyl ester 17, stearic acid methyl ester 18, 12 hydroxy stearic acid methyl ester 19, 12 methoxy stearic acid methyl ester 20, styrene 21, 2 (2 methoxyethoxy) ethanol 22, 1,1 oxybis(2 methoxy ethane) 23, benzoic acid methyl ester 24, adipic acid dimethyl ester 25, hexadecenoic acid methyl ester 26, dihydroisopimaric acid methyl ester 27, dehydroabietic acid methyl ester 28, 4 epidehydroabietol...

Propanol, titanium (4+) salt, 65, 230 2-Propanone, l-bromo-3-chloro-, dimethyl acetal, 65, 32 Propargyl bromide (106-96-7), 66, 77, 79, 86... 

If a diastereomeric mixture of (S,S)-2,5-dimethyl-3.4-hexanediol esters 2 and 3 reacts with methylmagnesium bromide, the result is kinetic resolution, as verified for R1 = Bn. The diastereomeric mixture was prepared from the racemic ethylene glycol a-chloro boronic ester via transesterification with chiral diol. The products isolated were (S,S)-2,5-dimethyl-3,4-hexanediol [(/ )-2-phcnyl-l-methylethyl]boronate, diastereomeric ratio >95 5 as indicated by the rotation of the (/ )- -phenyl-2-propanol derived by deboronation with hydrogen peroxide, and (S,S)-2,5-dimethyl-3.4-hexanediol methylboronate. Phenylacetaldehyde was identified by 1H NMR4. 

Propane, 2,2-dimethyl-l-phenyl-, 55, 112 Propane, 2-isocyano-2-methyl-, 55, 96 1.3-Propanedithiol, 56, 9 Propanesulfonyl cyanide, 57, 89 Propanoic acid, 2-chloro-, 56, 70 2-Propanol, 58, 133... 

Alkylated barbituric acids, 6-chloro-a-methylcarbazole-2-aceticacid, 1-phenylethanol, 1-phenyl-1-propanol, dimethyl, 3,4,5,6-pentafluoro-benzyl alcohol, l-(2-naphthyl)-ethanol, 1 -(p-biphenyl)-ethanol Chirasil-Dex coated column, 0.15 pm... 

Oxidation of Alcohols, Aldehydes, and Esters. Nitric acid oxidizes alcohols and aldehydes to the corresponding carboxylic acids. For example, l-chloro-3-propanol is oxidized to 3-chloropropanoic acid in 78-79% yield. 3-Chloropropional-dehyde affords the same product. Primary alcohols protected as esters are oxidized to the carboxylic acids (eq 11). In a two-phase solvent system (for example dimethyl ether and water), the oxidation of benzyl alcohols can be controlled so that aldehydes are obtained. ... 

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