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CA (620,000)
McGill (30,000)
Chemistry (1,000)
CHEM 222 (100)
Lecture

carboxylic acids.pdf


Department
Chemistry
Course Code
CHEM 222
Professor
David Harpp

This preview shows pages 1-3. to view the full 12 pages of the document.
CARBOXYLIC*ACIDS*
!"#$%&'()*+$,
!
IUPAC&
name&
common&
name&
salts&or&ester&
IUPAC&
name&
!
formic!
acid!
methanoic!
acid!
!
methanoate!
!
acetic!
acid!
ethanoic!
acid!
!
ethanoate!
!
propionic!
acid!
propanoic!
acid!
!
propanoate!
!
butyric!
acid!
butanoic!
acid!
!
butanoate!
!
valeric!
acid!
pentanoic!
acid!
!
pentanoate!
!
-+".$+,/0-12,%(#3%4,
The!preferred!system!of!nomenclature!is!the!IUPAC!system.!!
longest!chain!carrying!the!carboxyl!group!is!the!parent!structure!
“‐e”!of!alkane!becomes!!
o carboxylic!acids:!“‐oic!acid”!!
o salts!and!esters:!“‐oate”!
2"##"%,%(#$5,
Greek!letters!are!used!to!indicate!the!positions!of!substituents.!!
!
63(&375,
A!good!trick!to!remember!the!names!of!diacids!is!“oh!my,!such!good!apple!pie”.!!

Only pages 1-3 are available for preview. Some parts have been intentionally blurred.

!
2!
!
-+".$+)3$5,
897+"4$%,:"%73%4,
It!is!possible!for!carboxylic!acids!to!H‐bond!to!each!other.!This!dramatically!
increases!the!boiling!point.!!
;)+$%4)<,"=,(&37,
An!acid!is!a!stronger!acid!if!a!proton!can!easily!be!removed.!!
electronegative!groups!pull!electrons!from!surrounding!O!
o O!doesn’t!have!enough!electrons!and!will!pull!from!H!
H!is!more!positive!and!more!acidic!
the!more!electron‐withdrawing!groups!there!are!on!the!α‐C,!the!more!acidic!
the!acid!is!
o strongly!deactivating!pull!electrons!through!double!bonds!
NO2!
COOH!
COH!
COR!
o weakly!deactivating!donate!electrons!through!double!bonds!and!take!
electrons!through!single!bonds!
Cl!
Br!
I!
F!
-+$.(+()3"%,
>? @A37()3"%,"=,('&"<"'5B,('C$%$5,(%7,('C9':$%D$%$5,
Oxidation!is!either!adding!an!O!or!removing!an!H!from!the!C!being!oxidized.!!

Only pages 1-3 are available for preview. Some parts have been intentionally blurred.

!
3!
!
@A37()3"%,"=,.+3#(+9,('&"<"'5,
Primary!alcohols!have!2!hydrogens,!so!they!can!be!oxidized!twice.!!
PCC&will&oxidize&only&to&aldehydes.&&
!
Hot&KMnO4&and&H2CrO4&(called!Jones!reagent)!are&both&strong&oxidizing&
reagents,&and&will&oxidize&all&the&way&to&carboxylic&acids.&&
!
@A37()3"%,"=,5$&"%7(+9,('&"<"'5,
Secondary!alcohols!only!have!1!hydrogen,!so!they!can!only!be!oxidized!once.!The!
product!will!always!be!a!ketone.!!
PCC&and&hot&KMNO4&will&oxidize&secondary&alcohols&to&ketones.&&
!
@A37()3"%,"=,)$+)3(+9,('&"<"'5,
Tertiary!alcohols!do!not!have!a!hydrogen!available,!so!there!is!no!oxidation!possible.!!
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