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58 Cards in this Set

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  • Back
Elimination reactions commonly occur via the removal of ___ or ___?
alcohols, alkyl halides
What are the two types of elimination?
E1, E2
In the second step of E1, a proton on the beta carbon is removed by...?
a weak base
Higher temperatures tend to favor ___ over ___?
E1, Sn1
As a strong base removes a proton, a halide located ___ to the proton leaves, resulting in the formation of a double bond
anti
E2 reactions will often have ___ possible products, but the ___ substituted double bond will make up the larger percentage of the products
two, more
A ___base favors E2 over Sn2
stronger
Weak Lewis bases, aka ___ ___, favor ___ over ___
strong nucleophiles, Sn1, E2
T/F cyanide (CN-) and iodide (I-) are strong nucleophiles/ poor bases
true
A strong base will pull off a ___ hydrogen before it can reach the ___ carbon atom of the substrate, resulting in an E2 reaction
beta, alpha
With the help of a metal catalyst, alkenes can be reduced in a process known as ___ ___
catalytic hydrogenation
Typical metal catalysts include ___, ___, and ___
platinum, palladium, nickel
Catalytic hydrogenation has what type of addition?
syn
Reactions where only one stereoisomer is formed are called ___ reactions
stereospecific
A chemical reaction is ___ when a certain stereoisomer or set of stereoisomers predominate as products.
stereoselective
A reaction is ___ if different isomers lead to isomerically opposite products
stereospecific
The electrons in the double bond act as a Lewis ___ and react with the partially ___ hydrogen of HX molecules
base, positive
In an HX addition if the alkene is assymetrical the intitial protonation occurs at which carbon?
the least substituted/ the one with the most protons
To test for the presence of double bonds, sometimes a ___ ___ is used
diatomic halogen
The double bonds of alkenes can act as ___
nucleophiles (b/c the electrons of the pi bond are particularly reactive, so they are easily attacked by Lewis acids
The first step of the addition of the diatomic halogen results in ___ ___ ___
cyclic halonium ion
In diatomic halogen addition, the double bond attacks the ___ ___, with the ___ ___ acting as a ___ ___
diatomic halogen, second halogen, leaving group
The two halogens that are known to make cyclic halonium ions are...
chlorine and bromine
In diatomic halogen addition reactions the X- attacts the ion via ___ addition
anti
Water can added to alkenes under what kind of conditions?
acidic (most commonly H2SO4)
Addition of water must be completed at ___ temperatures
low
Hydration of the double bond can also be achieved under mild conditions with ___ ____
oxymercuration-reduction
Free-radical additions occure in the presence of ___, ___, or ___
peroxides, oxygen, UV light
Do free-radical additions obey or disobey Markovnikov's rule?
no
In free radical additions the halogen ends up on the ___ subsituted
least
In free radical additions the ___ adds first to the double bond
X "dot"
Free radical addition to alkenes is most useful for which halogen(s)?
bromine
Hydroboration occurs because ___ adds readily to double bonds
diborane (B2H6)/ borane (BH3)
The boron atom is a ___ ___ and attaches to the ___ sterically hindered carbon atom. At the same time, a ___ is transferred to the ___ carbon
Lewis acid, less, hydride, adjacent
The second step of hydroboration is an ___ ___ with ___ and ___ ___ that directly transfers ___ to the bond with boron producing an ___ with overall ___ ___, ___ orientation
oxidation-hydrolysis, peroxide, aqueous base, water, alcohol, anti-Markovnikov, syn
Alkenes can be oxidized with KMnO4, if it is ___, ___, and ___, the product has ___ added to ___. They have ___ addition.
cold, dilute, basic, -OH, each side of the double bond, syn
A ___, ___ solution of KMnO4 followed by ___ on nonterminal alkenes, they are cleaved to form ___ ___ ___ of ___. Terminal alkenes cleave to form a ___ and ___.
hot, basic, an acid wash, two molar equivalents, carboxylic acid, carboxylic acid, carbon dioxide
If the nonterminal double-bonded carbon is disubstituted, a ___ will be formed.
ketone
Ozonolysis will only cleave the double bond in half to become a ___ under reducing conditions. It will become a ___ is the starting molecule is disubstituted.
aldehyde, ketone
Ozonolysis under ___ conditions yields the same products as hot, acidic KMnO4
oxidizing
To obtain alcohols from ozonolysis, we have to ___ the aldehyde or ketone products with a mild ___ agent, such as NaBH4 (sodium borohydride) or the more potent LiAlH4
reduce, reducing
Alkenes can be oxidized with peroxycarboxylic acids such as peroxyacetic acid (CH3CO3H) and m-chloroperoxybenzoic acid (MCPBA). The products of these reactions are ___ aka ___. This reaction is an example of ___ addition
epoxides, oxiranes, syn
Polymerization requires ___ temperatures and ___. It usually occurs through a ___ mechanism.
high, pressure, radical
___ have larger dipole moments than ___.
alkynes, alkenes
Terminal alkynes are fairly ___. This means that terminal alkynes can stabilize ___ charge fairly well.
acidic, negative
One way to make triple bonds is through two rounds of ___ of a geminal or vicinal ___.
elimination, dihalide
A more useful method is to add an existing triple bond to a ___ carbon skeleton.
new
Terminal triple bonds can be converted to nucleophiles by removing its acidic proton with a ___ ___, such as ___ or ___
strong base, NaNH2, n-BuLi
What catalyst will stop an alkyne reduction from going to alkane? What is this catalyst made of?
Lindlar's, palladium on barium sulfate with quinoline
Lindlar's catalyst reactions have ___ addition because...
syn, they occur on a metal surface
Sodium in liquid ammonia is used to ___ alkynes to ___.
reduce, alkenes
Free radical addition to alkynes is also ___ ___, with the product usually being the ___ isomer
anti-Markovnikov, trans
Hydroboration of alkynes uses ___ addition, and what atom adds first?
syn, boron
When dealing with terminal alkynes, a ___ borane is used to prevent further boration of the vinylic intermediate to an ___.
alkane
Alkynes and alkens have the same products when reacted with what type of KMnO4?
hot, basic
When alkynes are reacted with ozone they yield ___ or ___. Terminal alkynes produce ___.
carboxylic acid, CO2, CO2
Cleavage of a primary double bonded carbon yields a ___. While cleavage of a secondary double bonded carbon results in a ___.
carboxylic acid, ketone
BH3/THF added to an terminal alkyne will produce ___ and ___ with internal alkynes.
aldehydes, ketones