




























































































Study with the several resources on Docsity
Earn points by helping other students or get them with a premium plan
Prepare for your exams
Study with the several resources on Docsity
Earn points to download
Earn points by helping other students or get them with a premium plan
Community
Ask the community for help and clear up your study doubts
Discover the best universities in your country according to Docsity users
Free resources
Download our free guides on studying techniques, anxiety management strategies, and thesis advice from Docsity tutors
Complete and schematic organic chemistry notes
Typology: Study notes
1 / 102
This page cannot be seen from the preview
Don't miss anything!
2
2
2
2
N
2
Na NHNa ONa ONa
2
Na NHNa ONa ONa
SeNa SNa ONa ONa
Br Cl
3
2
Na NHNa ONa ONa
3
3 < <
3 ° plus resonance
Br
Br
Br
Br
3 ° plus resonance
Br
Br
Br
Br
1° plus allylic
4
3
ethylene
oxide
1 º alcohol
R'MgBr
3
1 º alcohol
1 º alcohol
3
aldehyde
NaBH 4
3
or
ketone
2 º alcohol
3
H
NaBH 4
3
or
1 º alcohol
ester
3
2
Markovnikov
Markovnikov
2
R anti-Markovnikov
3
2
2
, NaOH
N
2 mech, needs 1 º or 2 º system
and an excellent leaving group
NaOH
Summary of Mechanisms, Ch. 10
For Test:
R Br + Mg
R + Br + Mg
Not for Test
3
aldehyde
or ketone
or formaldehyde
Z may be R (RMgBr)
or H (NaBH 4
or LiAlH 4
3
mech:
3
esters
or
acid chlorides
Z may be R (RMgBr)
or H (LiAlH 4 )
mech:
Cl
3
3
mech:
3
2
R Br RMgBr
Mg
R Br RLi + LiBr
2 Li
"Grignard Reagent"
R Br R MgBr
Mg Electrophile
R Electrophile
δ+
δ−
3
aldehyde
or ketone
or formaldehyde
3
mech: R'
acid chlorides
mech:
3
3
R Cl
esters or
acid chlorides
Addition Elimination
Addition
Protonation
fast
fast
O
R H
O
R R
O
R OR
Aldehyde Ketone Ester
Steric Advantage.
Transition-state less
crowded and more stable
Stablized for electronic reasons
Therefore less reactive
Relative
Reactivity:
H 2
O
or
ROH
Acid/Base
4
4
4
4
4
4
2
2
3
4
4
aldehyde
or ketone
or formaldehyde
3
mech: H
or
3
3
NaBH 4
3
or
NaBH 4
LiAlH 4
Addition Elimination
fast
3
Addition
Fast
ester
H
O
H
Addition
Elimination
H
O
H
H 3
O
H
O
O
O
O
O
O
H
OH
H
OH H 3
O
Double Protonation
H
Add
NaBH 4
= B H
H
H
H
H
B
H
H
Na + H LiAlH 4
= Al H
H
H
H
H
Al
H
H
Na
N
2
4
4
R OH R ONa
Acid-Base
R ONa
Na
Aldehydes
1 º Alcohols Only
2
CrO 4
= Na 2
Cr 2
7
2
4
or CrO 3
2
Ketones
2 º Alcohols Only
2
CrO 4
1 º Alcohols Only Acids
2
CrO 4
Acids Aldehydes
2
CrO 4
R Br
Mech: Be able to draw!
3 º alcohols
HBr
3
HBr
3 º mostly, sometimes 1 º
HBr Mech for 3 º ROH:
H Br
2
Br
R-Br
R-Br
2
HBr Mech for 1 º ROH: R OH
H Br
2
R-Br + H 2
PBr 3
Mech: R OH
Br
PBr 2
PBr 2
Br
Br R
HO-PBr 2
R-Br
R OH R ONa
Acid-Base
2
2
2
3
2
2
2
R OH
O
R O
O
OH
O
4
2
4
2
4
2
3
2
3
4
4
4
2
4
4
2
2
2
3
2
3
2
4
4
2
2
2
2 º alcohol
Aldehyde
Carboxylic
Acid
Ketone
or
1 º alcohol
or
oxidation
reduction
oxidation
reduction
Oxidation : The number of oxygen bonds to a carbon increases,
and the number of hydrogens bonded to a carbon decreases
Reduction : The number of oxygen bonds to a carbon is reduced,
and the number of hydrogens bonded to a carbon increases.
More General : # of bonds to heteroatoms versus to hydrogens
N
3
2
3
2
N
R Br
Mech: Be able to draw!
3 º alcohols
HBr
R Br
1 º or 2 º alcohols
PBr 3
or HBr
RMgBr
R Cl
1 º or 2 º alcohols
SOCl 2
HBr Mech for 3 º ROH:
H Br
2
Br
R-Br
2
HBr Mech for 1 º ROH:
H Br
2