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Chapter 10 Alkynes

Terms in this set (30)

Alkynes can be COMPLETELY reduced to alkanes via ______________ combined with ANY one of the following catalysts ______, _______, _______.
excess H2 gas, PtO2, Pd, Ni
Alkynes can be reduced to Z alkenes by what process_________? This involves a catalyst called ________ and what other substance______?
Catalytic hydrogenation, lindlar's catalyst, 1 equivalent H2
Alkynes can be reduced to Z alkenes by what process_______? This process can involve labeled alkenes if there is branching next to the triple bond. The first reactant step of the reaction involves _______, followed by the second reactant __________.
hydroboration-protonolysis, 9-BBN, CH3CH2CO2H
If an alkyne undergoes hydroboration-protonolysis the hydrogen of 9-BBN will be delivered to the carbon by the ________ site.
branching
Alkynes can be reduced to E alkenes by a ____________. This reactant substance is condensed to a liquid _________. Either ______ or ______ are added and form a blue solution.
dissolving metal reduction, NH3(l), Li, Na
When adding one equivalent of bromine to an alkyne the _____ dihalide forms from _____ addition.
E, anti
If there is an enyne and one equivalent of bromine is added which multiple bond will be reduced?
alkene
2-butyne is reduced to 2,2,3,3-tetrabromobutyne via what reactant?
xs Br2
Hydrogen halides add to terminal alkynes in a _______ manner.
markovnikov
An alkyne needs to be reduced to an alkene. We want to add Cl in a Markovnikov manner. What are the reactants?
1 eq HCl, CuCl
An alkyne needs to be reduced to an alkene. We want to add Br in a Markovnikov manner. What are the reactants?
1 eq HBr, FeBr3
This reactant will provide a monoadditon of HBr to to an alkyne, thus producing an alkene.
Et4N+Br-/HBr
This reactant will provide a monoadditon of HCl to to an alkyne, thus producing an alkene.
Et4N+Cl-/HCl
If an alkyne is exposed to this reactant, 2 Cl will be added to the more substituted carbon, and an alkane will be produced.
xs HCl
If an alkyne is exposed to this reactant, 2 Br will be added to the more substituted carbon, and an alkane will be produced.
xs HBr
If an alkyne is exposed to this reactant, 2 I will be added to the more substituted carbon, and an alkane will be produced.
xs HI
Terminal alkynes react slowly with ______ and ______ to give ketones.
H2O, H2SO4
________ are isomers that readily interconvert by a net [1,3] migration of proton accompanied by positional interchange of a single and double bond.
tautomers
Terminal alkynes react quicker to turn into ketones with the presence of ________ (type it out) otherwise known as _______ (formula). What other two substances are involved as reactants in this hydration reaction?
mercury II sulfate, HgSO4, H2O, H2SO4
Hydration of internal alkynes leads to a mixture of ketones unless the alkyne is ________.
symmetrical
An unsymmetrical alkyne that is exposed to the reactants HgSO4, H2SO4, and H2O will have how many products _____. A symmetrical alkyne that is exposed to those same reactants will have how many products_____?
2, 1
When an alkyne is hydrated via H2SO4, H2O, and HgSO4 what product is formed before the carbonyl is created?
enol
Terminal alkynes will undergo __________ to give aldehydes. The product will be a _______ addition. The first step of this reaction has the reactants ________, _______. The second step of this reaction has the reactants _______, ________.
hydroboration-oxidation, anti-markovnikov, 9-BBN, THF, HOOH, NaOH
Internal alkynes that are unsymmetrical will give a mixture of ketones via this process_______. First step reactants: _______ , _______. Second step reactants:_______, _______.
hydroboration-oxidation, 9-BBN, THF, HOOH, NaOH
An internal alkyne with branching at the alpha carbon will result in regioselectivity anti-markovnikov style where the _______ is placed on the carbon furthest away from the branching. How many products will be formed_____? First step reactants: _______ , _______. Second step reactants:_______, _______.
carbonyl, 9-BBN, THF, HOOH, NaOH
A symmetrical internal alkyne that undergoes hydroboration-oxidation will have how many products_____? A terminal alkyne that undergoes this same process will produce what______?
1, aldehyde
These reactant substances causes oxidative cleavage of internal alkynes into carboxylic acids. The first step reactants are _____? The second step involves acidification and the reactant is _______?
KMnO4, NaOH, hot, H2SO4
Terminal alkynes can be turned into a carboxylic acid and carbon dioxide via this process_____? The first step reactants are _____? The second step involves acidification and the reactant is _______?
oxidative cleavage, KMnO4, NaOH, hot, H2SO4
Ozonolysis (O3) followed by water turns internal alkynes into ________.
carboxylic acids
Ozonolysis (O3) followed by water turns terminal alkynes into ________. This is different from using hot potassium permanganate which produces the following products from a terminal alkyne _______.
carboxylic acids, carboxylic acid, CO2
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