TPR MCAT Organic Chemistry CH 4
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How are amides formed?
acid chloride + 1ry or 2ry amine in the precense of pyridine solvent
how are primary, secondary and tertiary amines formed? what type of reaction is this?
- Ammonia + 1)alkyl halide 2) NaOH
- SN2 reaction with inversion of configuration
to make react product subsequently in the same manner to make 2ary, and 3ry amines
- so NH3+R-X > RNH2 (in NaOH)
- RNH2 + R-X > R2NH2 etc.
What is product of an amide + Nitrous acid?
carboxylic acid + Nitrogen gas.
What is a hoffman elimination?
How is it performed?
what products are formed?
The elimination of a carbonyl group from an amide.
amide is reacted with NaOH, Br2 in H2O
the product is an amine + CO2 (g)
RCONH2 >(NaOH, Br2 in water)> R-NH2 + CO2 (g)
What do electron withdrawing groups do to arylamides?
What are some electron donating groups?
- Decrease basisity
- -Cl, -NO2, -CN
What do electron donating groups do to arylamines?
What are some of these groups?
-CH3, -NH2, -OCH3
How are aldehydes and ketones made?
Oxydation of 1ry or 2ary alcohols with PCC or O3, CrO3, or KMNO4
how are alcohols made from ketones or aldehydes?
reduction of ketones or aldehydes with strong reducing agents like NaBH4 or LiAlH4
How are acetals made?
reacting an aldehyde or ketone with 2eq of alcohol in acid
what is acetal overal reaction?
carbonyl d-bond gets replaced by to OR bonds to the 2eqs of alcohol
How are imines formed?
reacting aldehydes or ketones with 1ry or 2dary imines in precense of buffer.
what is imine overal reaction?
Carbonyl d-bond gets replaced by d-bond to Nitrogen, which retains alkyl substituents from original amine
What are aldol condensations used for?
to elongate molecules making carbon-carbon bonds
overal aldol condensation reaction
what are parent compounds?
What is the product?
d-bond of one of first carbonyl splits and bonds to an OH on one side, and to alpha carbon of other carbonyl on the other side.
Parent compounds are two carbonyls
What is the product of an aldol condensation dehydration?
How is it carried out?
product is: alpha,Beta-unsaturated carbonyl
What is the overal addition reaction to alpha, Beta-Unsaturated carbonyl compounds?
Acid catalized addition of a nucleophile to the unsaturated B carbon.
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