Reactions of Alkenes Flashcards
3 TYPES OF MAIN REACTIONS of alkenes
- Addition Reactions
- Hydroxylation and Oxidative Cleavage
- Epoxidation
4 types of ADDITION REACTIONS of alkenes
- Catalytic Hydrogenation
- Electrophilic Addition
- Free Radical Addition
- Free Radical
Polymerization
ADDITION RXN
- an ___ to a ____ process* wherein the ___ bond is DISRUPTED
- change of hybridization from ___ to ____
- change of electron geometry from ____ to ____
*difference between the 2
- unsaturated to saturated
- pi
- sp2
- sp3
- trigonal planar
- tetrahedral
🔹 Unsaturated → Contains at least one double (C=C) or triple (C≡C) bond
🔹 Saturated → Contains only single (C-C) bonds
ADDITION RXN - CATALYTIC HYDROGENATION
- addition of ____ to the ___ of alkene
- from double bond, it becomes ____ bond
- reaction with ____ ____ ____, usually… (3)
- stereochemistry?
- what type of heat rxn?
- releases a specific amount of _____ when ___ mole of ______ compound undergoes _____ to form a _____ compound (+ which is called?)
- wherein the lower its value, the _____ the stability of the alkene
- H2 -> C=C
- single
- solid metal particles
- PtO2
- Pd/C
- Pt/C
- syn addition
- exothermic reaction
△H, heat of hydrogenation
- amount of heat
- 1 mole of unsaturated
- hydrogenation
- saturated compound
- greater
ADDITION RXN - ELECTROPHILIC RXNS
5 types
- Addition of hydrogen halide (HX)
- Addition of H2O (hydration)
- Addition of cold concentrated H2SO4
- Addition of Halogens (X2)
- Halohydrin Formation
ADDITION RXN - ELECTROPHILIC RXNS
ADDITION OF HX
- intermediate?
- stereochemistry?
- regioselectivity?
- more stable carbocation
- syn and anti addition products
- markovnikov’s rule
ADDITION RXN - ELECTROPHILIC RXNS
ADDITION OF H2O
- POSSIBLE reagents (2)
- intermediate?
- stereochemistry?
- regioselectivity?
+ forms what in the products?
REAGENTS:
- H2O and H3O+
- dilute H2SO4
- more stable carbocation
- syn and anti addition products
- markovnikov’s rule
OH - more substituted C
H - less substituted C
ADDITION RXN - ELECTROPHILIC RXNS
ADDITION OF COLD CONCENTRATED H2SO4
- POSSIBLE reagents (1)
- intermediate?
- stereochemistry?
- regioselectivity?
+ forms what in the products?
- cold, conc. H2SO4
- more stable carbocation
- syn and anti addition products
- markovnikov’s rule
OSO3H - more substituted C
H - less substituted C
ADDITION RXN - ELECTROPHILIC RXNS
ADDITION OF HALOGENS (X2)
- what halogens can be used (2)?
- solvent (2)?
- intermediate?
- stereochemistry?
- regioselectivity?
+ chemical test used + process + results
- Cl2 or BR2
- CCl4 or CHCl2
- cyclic halonium ion
- anti-addition
- none
BROMINATION TEST
chemical test used to determine if what was reacted with the Br2 (with CCl4 solvent) is truly an unsaturated compound (alkene)
if it is an alkene, the orange color of bromine will disappear
ADDITION RXN - ELECTROPHILIC RXNS
HALOHYDRIN FORMATION
- reagents?
- intermediate?
- stereochemistry?
- regioselectivity?
- unique characteristic?
- products (2)
- Cl2 or Br2 + H2O
- cyclic halonium ion
- anti-addition
- Markovnikov’s Rule
OH - more substituted C
X - less substituted C
alkane w/ OH and X + HX
ADDITION RXN - FREE RADICAL ADDITION of HBr
- reagents?
- intermediate?
- regioselectivity?
- HBr and ROOR’ in presence of light
- free-radical
- Reverse Markovnikov
H - more substituted C
Br - less substituted C
ADDITION RXN - FREE RADICAL POLYMERIZATION
- general formula
- reagents?
- ____ bond of the _____ disappears and connects with the molecule’s ______ ______
- draw general formula
- ROOR
- π
- C=C
- repeating units
ADDITION RXN - FREE RADICAL POLYMERIZATION
if for example, the ff compounds underwent polymerization, what will be the name of their products?
- styrene
- ethylene
- propylene
- polystyrene
- polyethylene
- polypropylene
WHAT is used in the identification of the type of resin used in a manufactured article
RESIN ID CODES
HYDROXYLATION
- reagents + formal term for it?
- stereochemistry?
- products (2)?
+ chemical test + process + positive result
- cold, dilute, neutral KMnO4 (Baeyer’s Reagent)
- syn addition
- vicinal diol or 1,2-diol (contains 2 OH molecules) + MnO2
BAEYER’S TEST
- test if a compound is unsaturated (alkene)
- loss of purple color of KMnO4
- formation of brown MnO2 precipitate
OZONOLYSIS
- reagents?
- ozone is _____ and ____ _____ bonds ____
- 2 possible products
- O3 with Zn, H3O+
- non-selective
- cleaves all bonds simultaneously
- Ketone
- Aldehyde
OXIDATIVE CLEAVAGE RXNS w/ ACIDIC KMnO4
- reagents?
- 3 possible products?
- KMnO4, H3O+
- carboxylic acid
- carbon dioxide
- ketone
EPOXIDATION
- reagent?
- products (2)?
- m-chloroperoxybenzoic acid (MCPBA)
- epoxide (cyclic ether) + MCBA
RELATIONSHIP between stability and energy
INVERSE
the lower the energy, the higher the stability
PALATANDAAN on where reagents are added per C during a rxn?
PER C ng C=C or even C≡C makakakuha ng reagent
kunwari, sa addition of HBr, yung H and Br ay BAWAL sa same C mag-a-attach
