Synthesis Of alcohols Flashcards
General method for preparing alcohols
Reduction of a carbonyl compound
What do carbonyl compound add to a C=O bond and what does it give
Adds hydrogen giving alcohol
True or false: all kinds of carbonyl compounds can be reduced, including aldehydes, ketones, carboxylic acids, and esters
True
In a carbonyl compounds H is the
Reducing agent
What do aldehydes reduce
To give primary alcohols, and ketones to give secondary alcohols
Esters and carboxylic acids are reduced to give
Primary alcohols
Carboxylic reduction is not as rapid as the reductions of aldehydes and ketones so
More powerful reducing agent lithium aluminum hydride (LiAlH4) is used rather than NaBH4
More powerful, less specific, and very reactive with water
(LiAlH4)
Also reduce aldehydes and ketones
LiAlH4
Both __ and __ add the equivalent of the hydride ion “H-“
NaBH4; LiAlH4
Only one H added to carbonyl carbon during the reduction of aldehyde or ketone but two for
An ester or carboxylic acid
Grignard reagents (RMgX) involves addition of carbanion (R:-+MgX)
Grignard reaction
Prepared by reaction of organihalides with magnesium, react with carbonyl compounds to yield alcohols
Grignard reagents (RMgX)
Formaldehyde, H2C=O reacts with grignard reagents giving
Primary alcohols, aldehydes give secondary alcohols, and ketone give tertiary alcohols
Sters react with grignard it yields
Tertiary alcohols in which two substituents bonded to hydroxyl -bearing carbon