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ALDEHYDES AND KETONES Chapter 9
Chemistry of the Carbonyl Group TAB I - Carbonyl Reactivity
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t i ‘The -H and -X in thes
0 comspomndls ca’ act 2
RH ORT R loaving groups in substitution
Aldehyde Ketone reactions
9 9 9
ae oe:
Ron RT oR RT a
Carboxylic Aster Acid chloride. ‘Pho -OH, -OR’, -C,
acid -NFp, and -OGOR’ in
these compounds.can act
as leaving groups in
q q t substitution reactions,
©. C6.
RO NT, oR OT “RF
Amide Acid auhydvide
Naming Aldehydes and Ketones
aldehyde - longest chain contains -CHO group, replace -e suffix of alkane with -al, numbering
begins with C of CHO; suffix -carbaldehyde used when CHO attached to a ring
EX 1. Give an IUPAC name for the following aldchydes:
CH,C(CH;),CH,CH,CHO CH, = CH(CH,);CHO HO(CH,),CHO
EX 2. Give an IUPAC name for the following common aldehydes:
HCHO (formaldehyde) CH;CHO (acetaldchyde) CHO (benzaldehyde)
ketone ~- longest chain contains carbonyl, replace alkane -e suffix with -one, numbering gives
carbonyl the lower number; can be named as a ketone; carbonyl oxygen is an -oxo substituent
EX 3, Draw structures for these molecules:
4-methylpentan-2-one methyl ethyl ketone 2-methyl-4-oxopentanal
EX 4. Give an JUPAC name for the following common ketones:
CH,COCH; (acetone) COCH; (acetophenone) &CO® (benzophenone)
2
Synthesis of Aldehydes and Ketones - oxidation of alcohols
formal oxidation of a primary alcohol
0
RCH, -OH 1, eRcHO
formal oxidation of a secondary alcohol
, [0] :
RRCH-OH ~-> RCOR
acidic permanganate oxidation of a secondary alcohol
{acidic permanganate oxidation of alkenes)
KMnO,
2H on one C=C carbon > CO,: CH;CH = CH, a or > CH,COOH + CO,
3
KMnO,
1H on one C = C carbon — COOH: CH,CH = CHCH, hor > 2CH;COOH
3
KMnO,
no Hon C=C carbon > ketone: (CH;).C = C(CHs)2 Tho" > 2CH;COCH;
3
Formal Oxidation and Reduction
CH,;-CH; <=> CH),=CH, <=> CH=CH
CH, <=> CH,0H <=> HCHO <=> HCOOH <=> CO,
CH,CH; <=> CH,CH,OH <=> CH;CHO <=> CH,COOH
CH,CH,CH, <=> CH;CHOHCH, <=> CH,COCH,
