Tertiary alcohol carbon

Both the Bogert and Cook groups continued to develop the scope and limitations of these cyclizations and other groups joined the task. During this work, two different spirocycles were reported to be formed. The first at the tertiary alcohol carbon, derived from the point of attachment of the phenylpropanyl moiety. For example, closure to form the six-membered spirocyclic ring for two compounds was reported to occur in about 90% yield from alcohols 12 and 14. 

The following tertiary alcohols may be prepared from the appropriate Grignard reagent and diethyl carbonate in yields of 75-80 per cent. 

Alcohols and alkyl halides are classified as primary secondary or tertiary according to the degree of substitution of the carbon that bears the functional group (Section 2 13) Thus primary alcohols and primary alkyl halides are compounds of the type RCH2G (where G is the functional group) secondary alcohols and secondary alkyl halides are compounds of the type R2CHG and tertiary alcohols and tertiary alkyl halides are com pounds of the type R3CG... 

Because tertiary alcohols are so readily converted to chlorides with hydrogen chlo nde thionyl chlonde is used mainly to prepare pnmary and secondary alkyl chlondes Reactions with thionyl chlonde are normally carried out m the presence of potassium carbonate or the weak organic base pyndme... 

Primary alcohols do not dehydrate as readily as secondary or tertiary alcohols and their dehydration does not involve a primary carbocation A proton is lost from the (3 carbon m the same step m which carbon-oxygen bond cleavage occurs The mechanism is E2... 

The type of alcohol produced depends on the carbonyl compound Substituents present on the carbonyl group of an aldehyde or ketone stay there—they become sub stituents on the carbon that bears the hydroxyl group m the product Thus as shown m Table 14 3 (following page) formaldehyde reacts with Grignard reagents to yield pri mary alcohols aldehydes yield secondary alcohols and ketones yield tertiary alcohols... 

Reaction of Grignard reagents with es ters (Section 14 10) Tertiary alcohols in which two of the substituents on the hy droxyl carbon are the same may be pre pared by the reaction of an ester with two equivalents of a Grignard reagent... 

A method that allows for alcohol preparation with formation of new carbon-carbon bonds Primary sec ondary and tertiary alcohols can all be prepared... 

Tertiary alcohols have no hydrogen on their hydroxyl bearing carbon and do not undergo oxidation readily... 

In the presence of strong oxidizing agents at elevated temperatures oxidation of tertiary alcohols leads to cleavage of the various carbon-carbon bonds at the hydroxyl bearing carbon atom and a complex mixture of products results... 

Amyl alcohol describes any saturated aliphatic alcohol containing five carbon atoms. This class consists of three pentanols, four substituted butanols, and a disubstituted propanol, ie, eight stmctural isomers four primary, three secondary, and one tertiary alcohol. In addition, 2-pentanol,... 

Esters react with two equivalents of a Grignard reagent to produce tertiary alcohols. Two of the groups bonded to the carbon that bears the hydroxyl group in the tertiary alcohol are derived from the Grignard reagent. 

Citrate itself poses a problem it is a poor candidate for further oxidation because it contains a tertiary alcohol, which could be oxidized only by breaking a carbon-carbon bond. An obvious solution to this problem is to isomer-ize the tertiary alcohol to a secondary alcohol, which the cycle proceeds to do in the next step. 

Sm, I2, MeOH, it, 3-60 min, 95-100% yield. Tertiary alcohols were not affected. As the reaction time and temperature are increased, benzoates and carbonates can also be cleaved. ... 

The behavior of unsaturated azlactones with organometallic reagents has been studied in detail. Arylmagnesium halides and phenyllithium attack 4-arylidene-5-oxazolones at the carbonyl carbon to give ring-opened amido tertiary alcohols (26) and oxazolines (27) (by ring closure), usually as mixtures [Eq. (17)]. The nature of the... 

The substitution of the lone proton on the benzhydryl carbon by a methyl group again affords compounds with antihistamine activity. Reaction of an appropriate acetophenone (21) with phenyl-magnesium bromide affords the desired tertiary alcohols (22). 

The terms primary- secondary, tertiary, and quaternary are routinely used in organic chemistry, and their meanings need to become second nature. For example, it we were to say, "Citric acid is a tertiary alcohol," we would mean that it has an alcohol functional group (-OH) bonded to a carbon atom that is itself bonded to three other carbons. (These other carbons may in turn connect to other functional groups). 

Esters react with Grignard reagents to yield tertiary alcohols in which two of the substituents bonded to the hydroxyl-bearing carbon have come from the Grignard reagent, just as LiAlH4 reduction of an ester adds two hydrogens. 

Mass 59 for tertiary alcohols with two methyl groups on the a-carbon,... 

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