Chapter 10
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Acidity of Alchohols
The acidity decreases as the substitution on the alkyl group increases.
What solvent is needed for forming Grignard reagents?
An Ether R-O-R
In addition of a Grignard reagent, what other reactant should you use to form primary alcohols?
Formaldehyde
In addition of a Grignard reagent, what other reactant should you use to form secondary alcohols
Aldehydes
In addition of a Grignard reagent, what other reactant should you use to form tertiary alcohols?
Ketones
What does addition to acid chlorides and esters produce?
2 R-MgX + acid chloride/ester = tertiary alchohol
Groups that protonate the Grignard or organolithium
O-H N-H S-H C=-C-H
Groups that attack the Grignard or organolithium
C=O C=N C=-N S=O N=O
What is NaBH4 used for?
NaBH4 reduces: aldehydes —> primary alcohols ketones —> secondary alcohols
What solvents are used for NaBH4 reduction?
Acohols, ethers, and water.
What is LiAlH4 used for?
• Much stronger than sodium borohydride Reduces: ketones —> secondary alcohols aldehydes, acids, esters —> primary alcohols
What solvent is used for LiAlH4 reduction?
Dilute acid
When deciding at what end of the chain to start, which has more priority? OH or a double bond
Alcohol groups have higher priority than double bonds (chain begins closer to alcohols)
Naming diols
Indicate place where OHs are and leave the main carbon chain with “ane” ending - (1-phenylhexane-1,5-diol)
When is the term “glycol” used in naming?
Glycol is used when 2 alcohols are vicinal to each other
What is a “thiol” group?
HS
How do you transform a thiol (SH) into a sulfonic acid (SO3H)?
Use a strong oxidizing agent like: KMnO4, HNO3, or NaOCl
How many hydrogens do NaBH4and LiAlH4 add to ketones and aldehydes?
2 Hydrogens
How many hydrogens does LiAlH4 add to acids and esters?
3 Hydrogens
What is ethylene oxide?
