CHM 2211 Chapter Notes - Chapter 22: Trigonal Planar Molecular Geometry, Thioester, Stage Name
-Carboxylic Acids -
-Ch 22 focuses On Carbonyl compounds that contain an
acyl group bonded to an electronegative atom .
include : Carboxylic acids ,acid Chlorides
,
an hydrides ,
acyl phosphates ,esters
,
+ hio esters ,&amines
.
R-
CIN :
2°
,
30
et
-
-AND BONDING -
no
.gg#Po2hYbridi2ed .ae#roPwTarbon
=
"" "
•
to :
Trigonal planar
5'
S-
\
an crowded 1
the more
resonance
=
more
Stable
*The more basic Zis
,
the more it donates
its electron pair &the move resonance 3
contribute S
*More basic Z is -7 more stable 12=2
is
* like Carboxylic acid derivatives ,
nitriles contain an electro pnilic Carbon
=Susceptible to nucleophilic attack
-AND BONDING -
Problem 22.2 ; Draw the three sossibie resonance
Structures for thio ester &an ester . Then
, using pka
Values (table 22.1 )decide if a thioester is more or
less resonance stabilized than an ester .
:O
::O
:O .:O
:O
Hc- 1+0 -
l
/'&R
'/\ .sn/rN.s.E.
Th Th ..
Thi o ester
\
less basic
..-0
:O :io
:
io
:O
11 c- ,to c- ,
I
n/
RER th &R m/× .FR
\
ester more basic
P In a l S. S-18
= more resonance Stabilized
Problem 22.3 :
finish
Document Summary
Carbonyl compounds that contain an acyl group bonded to an electronegative atom include. Chlorides an hydrides , acyl phosphates esters hio esters amines. Z is the more it donates the move resonance. Carboxylic acid derivatives nitriles contain an electro pnilic. 22. 1 decide less resonance stabilized three sossibie resonance if an a ester. Then using pka thioester is more or than an ester. Anhydride symmetrical replace acid acid ending alphabetize with. To from acetic acid benzoic acid acetic benzoic anhydride. Amide replace ic acid or ylic oic acid acid with. H formic acid from acetic acid ethyl it. 2 must be a better leaving group than. Can"t if be use used to make acid. Rxns can be in acid or base hydrolyed with water p. %aa. at#9ohr%a0rfmo. +h - or. Ketone by an i mine which the reverse of. What reagents are needed to convert phenylacetonitrile (c6h5ch2cn) to each compound: (a) c6h5ch2coch3; (b) c6h5ch2coc(ch3)3; (c) c6h5ch2cho; (d) c6h5ch2cooh? a b.
