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An in-depth exploration of alkenes, their structure, nomenclature, and reactivity. It covers topics such as the naming of alkenes, their physical properties, the formation of cis and trans isomers, and their reactions with various electrophiles and nucleophiles. The document also discusses the role of electrophilic and nucleophilic reagents in the addition reactions of alkenes.
Typology: Schemes and Mind Maps
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: Find the longest chain containing the double bond and name the Rule
1: Find the longest chain containing the double bond and name thecompound by replacing the alkane suffix –ane with –ene. Rule 2: Number carbons in the chain so that double bond carbons have the
lowest possible numbers; if the double bond is equidistant from twoends, begin at the end nearer the first substituent.
8-
vinylic carbons
Hex-2-ene
2-Methylhex-3-ene
allylic carbons
vinyl
2 Eth l
t
1
2 - Methyl
buta
- 1 3-
diene
_____ group
gro p vinyl allyl
2 -Ethylpent-1-ene
2-Methylbuta-1,3-diene- diene
and -
triene
allyl _____ group
m.p. -
o C b.p. 4
o C
m.p. -
o C b.p. 1
o C
-^ E^
hi^ h
l
higher
lower
lower
higher
higher
higher
lower
lower
g
lower
lower
8-
more hyperconjugation
o ∆ H
follows Zaitsev’s rule
Elimination Reactions:
An E2 reaction that generatesthe thermodynamically lessfavored isomer is said tofollow the
Hofmann rule follow the
Hofmann
rule.
Dehydration of Alcohols:
8-
Reactivity in dehydration:o^1
o< 2 < 3
o^ alcohols
This atom has ____________from
(^2) sp to^ sp
3
re-hybridized
The brackets denote
This carbon now has an empty
The
brackets denote an ___________ alongthe reaction pathway
intermediate
p orbital; its incomplete octet(6 electrons) makes it electrondeficient
Product Distribution and
the Reaction Coordinate Diagramthe Reaction Coordinate Diagram
For this step the TS
≠^ is
For^
this step, the TS
is
late. Thus, we orderedthe energies of the TS
≠s
according to the energiesaccording to the energiesof the intermediates.
8-
Electrophilic Addition: Alkyl Halide Preparation^ •
(CH
)C=CH 3 2
2
CH
CH=CHCH 3
3
CH
CH=CH 3
2
CH
=CH 2
2
(CH
)C=CH 3 2
CH 2
CH=CHCH 3
CH 3
CH=CH 3
CH 2
=CH 2
2
Rearrangement of Carbocations
8-
Electrophilic Hydration of Alkenes
Alkene hydration and alcohol dehydration are equilibrium processes.
catalytic^ H
+
catalytic H
+^
more stable; major componentin isomeric product mixture
Electrophilic Addition of Halogen to Alkenes
8-
a racemic mixture (
± )
Stereochemistry Elucidates the Mechanism
- Br
a carbocation wouldbe trigonal planar
Bromonium Trapped by Other Nucleophiles
( ± )
Br^2 CH^ OH^3
( ± ) ( ± )
8-
Regioselectivity in Halonium Ion Opening
Carbene and Carbenenoid Reactions
bicyclo[4.1.0]heptane
cis -diethylcyclopropane
Simmons-Smith reagent
: (iodomethyl)zinc iodide
“^ b
id
” (^
b^
lik^
b t^
)
“ carbenoid
”^ (a carbene-like substance)
8-
92%
Reduction of Alkenes: Catalytic Hydrogenation
syn-
addition
1
diastereoselective diastereoselective
Oxidation and Reduction in Organic
ChemistryChemistry
8-
an epoxide
Epoxide Synthesis electrophilic
via halohydrin:
Diol Formation: Epoxide Ring-Opening
vicinal
anti dihydroxylation
8-
Vicinal
Syn
Dihydroxylation of Alkenes
Not very useful forsynthesis: easily over-oxidized into ketones
cold, dilute(w/ NaOH)
oxidized into ketonesand/or carboxylic acids.
Use of OsO
or NaHSO
3
Use
of OsO
+ OsO+^ OsO
3
3
8-
a^ syn
vicinal diol
OsO
: expensive and toxic 4
Oxidative Cleavage: Ozonolysis
( or^ CH
SCH 3
) 3
mechanism:
8-
More Oxidative Cleavages to Carbonyl
CompoundsCompounds
KMnO
4
+ H
4
4
or NaHSO
3
8-