Chapter 2: Acids + Bases
pka = -
log(ka) &
stronger acid will behave as the acid
& Ea favors formation of weaker acid &
↳ acid
smaller
pla =
stronger
pkoni
< 8 s ~
以B ⼀⽀ S =
고5 -
BS =
나나 msg ∞
⑦ ‰ θ
SP sp
?
S☆
}
ROHz RNH EH 니
-Old BNISS ROH HC ≡ C6 Ha C CHr CHsCH3
=
로
,
0.
, 7
( -
p ⑩.
⾅⼀町 x
H 2
O
stable
H 300 resorance base more
pstability
∞ = weaker !:
_
p Keq
=
pKa (reactant) pKa (product) acid strength is determined by stability of base
ㅣ
-
con.
< I reactants favored
,
A
.
Electronegativity
:
strongest add has It attached
> 182 , products favered to Most ent atom
electrophile Frsmosew
Lewis acid :
7 with
_
CENC 84
accepts a share in
: ~>
strongest se
Lewis base : donates share inè <
NAS < 1620 < HE
paircleophile CHu
a :
- most
sp3
\
EN
ex
>
- : Lone pair <
sp2 <
Sp H Y BRIDIZATION
Nuclesphile e HOMO < > ti
E stronges
-
←
Electrophile => LUMO-
-
eX : avail . Mo like sorb
or
*
Orbital
attached to
strongest acid
⼀
绍 ,
Size : has I
largest atom
A R J ㅇ rostrongest
HI )
휼 뮴
훔 5 UFC ICI /Br < in COLUMN
흖 . Inductive
2 electron withdrawal : EWG pulls e-
through Sigma bonds ,
making Con base
.
more
if : stable
- has an Ho to give
↑ <
pKa = acidic form
Ht
pl >
plat basic form - wants to
accept an
more EN the sub >
-
more inductive power
s
☆ ‰ closer the sub to i more inductive power
j -0
"
163
'
→
H=
6
pka ns D
. Electron delocalization stabilizes con base by
喈
= :
pHt
pka lowering density through
<
resonance
pka > pl b
b basic form
acidic
'
, Ch . 3 : Intro to Organic Compounds
methyl
-
3V1 butyl
constitutional isomers : same molecular formula
s
Λ
atnge
* isobutyl
connected
but atoms
differently
↳
#V propyl xX-sec-butyl
2C 2 H X + N
first
+ -
-
determine DoV =
↳ j = doub.
고
* isopropyl 5k tert-butyl
bond or
ring
IUPAC
Naming Rules : Newman projection : there are different "spatial
1
.
Longest cont .
chain (containing func grps) arrangements" of the atoms that result from rotation
conformational isomers
2
2 Name
alkyl subs w/ number, order so subs have about
single bond
a -
lowest# possible
"
H
H
-
H
chains hyperconjugation
-
.
3 If2 same length parent chain w
⇌
=
,
짐 的\ staggered
Stabilizes
greatest# subs " "
*
Corbs parallel)
4
4. Chly alkane staggered eclipsed
↳
ring w/2 subs gives 1 in alpha order +
next more stable
lowest # possible
steric strain : repulsion btw . e cloude
Chair conformation:
⇌
axia up (60%
Gauche
in
ex : butane
* ea
T \
down
OH3 H C
.
s
-
jeg up plsts
D
1. d cls Gl4s ,
It
↑↓ 1
axial down more each C
clockwise 1 pos .
4
8"
,
t 16 歩 "
10
明
) ↓ 成 ↓10 λ
↓
。
* subsituents more stable ~
eclipsea
position
Lea
in EQUATORIAL ANTI
,
이≈〜.
↳ each axial substituent has I_
1 3-diaxial interactions
℃
↳
ㅇ
can also see gauche interactions in chairs
most
stable
barrier to rotation diff btw of each
energies
=
℃ conformation
ル TJanm
'
H
me
,Yin 可 - i "
×
↓
more stable
pka = -
log(ka) &
stronger acid will behave as the acid
& Ea favors formation of weaker acid &
↳ acid
smaller
pla =
stronger
pkoni
< 8 s ~
以B ⼀⽀ S =
고5 -
BS =
나나 msg ∞
⑦ ‰ θ
SP sp
?
S☆
}
ROHz RNH EH 니
-Old BNISS ROH HC ≡ C6 Ha C CHr CHsCH3
=
로
,
0.
, 7
( -
p ⑩.
⾅⼀町 x
H 2
O
stable
H 300 resorance base more
pstability
∞ = weaker !:
_
p Keq
=
pKa (reactant) pKa (product) acid strength is determined by stability of base
ㅣ
-
con.
< I reactants favored
,
A
.
Electronegativity
:
strongest add has It attached
> 182 , products favered to Most ent atom
electrophile Frsmosew
Lewis acid :
7 with
_
CENC 84
accepts a share in
: ~>
strongest se
Lewis base : donates share inè <
NAS < 1620 < HE
paircleophile CHu
a :
- most
sp3
\
EN
ex
>
- : Lone pair <
sp2 <
Sp H Y BRIDIZATION
Nuclesphile e HOMO < > ti
E stronges
-
←
Electrophile => LUMO-
-
eX : avail . Mo like sorb
or
*
Orbital
attached to
strongest acid
⼀
绍 ,
Size : has I
largest atom
A R J ㅇ rostrongest
HI )
휼 뮴
훔 5 UFC ICI /Br < in COLUMN
흖 . Inductive
2 electron withdrawal : EWG pulls e-
through Sigma bonds ,
making Con base
.
more
if : stable
- has an Ho to give
↑ <
pKa = acidic form
Ht
pl >
plat basic form - wants to
accept an
more EN the sub >
-
more inductive power
s
☆ ‰ closer the sub to i more inductive power
j -0
"
163
'
→
H=
6
pka ns D
. Electron delocalization stabilizes con base by
喈
= :
pHt
pka lowering density through
<
resonance
pka > pl b
b basic form
acidic
'
, Ch . 3 : Intro to Organic Compounds
methyl
-
3V1 butyl
constitutional isomers : same molecular formula
s
Λ
atnge
* isobutyl
connected
but atoms
differently
↳
#V propyl xX-sec-butyl
2C 2 H X + N
first
+ -
-
determine DoV =
↳ j = doub.
고
* isopropyl 5k tert-butyl
bond or
ring
IUPAC
Naming Rules : Newman projection : there are different "spatial
1
.
Longest cont .
chain (containing func grps) arrangements" of the atoms that result from rotation
conformational isomers
2
2 Name
alkyl subs w/ number, order so subs have about
single bond
a -
lowest# possible
"
H
H
-
H
chains hyperconjugation
-
.
3 If2 same length parent chain w
⇌
=
,
짐 的\ staggered
Stabilizes
greatest# subs " "
*
Corbs parallel)
4
4. Chly alkane staggered eclipsed
↳
ring w/2 subs gives 1 in alpha order +
next more stable
lowest # possible
steric strain : repulsion btw . e cloude
Chair conformation:
⇌
axia up (60%
Gauche
in
ex : butane
* ea
T \
down
OH3 H C
.
s
-
jeg up plsts
D
1. d cls Gl4s ,
It
↑↓ 1
axial down more each C
clockwise 1 pos .
4
8"
,
t 16 歩 "
10
明
) ↓ 成 ↓10 λ
↓
。
* subsituents more stable ~
eclipsea
position
Lea
in EQUATORIAL ANTI
,
이≈〜.
↳ each axial substituent has I_
1 3-diaxial interactions
℃
↳
ㅇ
can also see gauche interactions in chairs
most
stable
barrier to rotation diff btw of each
energies
=
℃ conformation
ル TJanm
'
H
me
,Yin 可 - i "
×
↓
more stable
