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CC CC
AlkynesAlkynes
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Synthesis of AcetyleneSynthesis of Acetylene
Heating coke with lime in an electric furnace to Heating coke with lime in an electric furnace to forms calcium carbide.forms calcium carbide.
Then drip water on the calcium carbide.Then drip water on the calcium carbide.
H C C H Ca(OH)2CaC2 + 2 H2O +
C CaO3 + +CaC2 COcoke lime
*This reaction was used to produce light
for miners’ lamps and for the stage.
*
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The Structure of Alkynes
A triple bond is composed of a bond and two bonds
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QuestionQuestion
Arrange ethane, ethene, and ethyne in order of increasing C-C bond length.
A) ethane < ethene < ethyne
B) ethene < ethane < ethyne
C) ethyne < ethene < ethane
D) ethane < ethyne < ethene
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HH CC CC
Acidity of AcetyleneAcidity of Acetylene
and Terminal Alkynesand Terminal Alkynes
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In general, hydrocarbons are In general, hydrocarbons are very weak acidsvery weak acids
CompoundCompound ppKKaa
HFHF 3.23.2
HH22OO 1616
NHNH33 3636
4545
CHCH44 6060
HH22CC CHCH22
Acidity of HydrocarbonsAcidity of Hydrocarbons
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Acetylene is a weak acid, but not nearlyAcetylene is a weak acid, but not nearlyas weak as alkanes or alkenes.as weak as alkanes or alkenes.
CompoundCompound ppKKaa
HFHF 3.23.2
HH22OO 1616
NHNH33 3636
4545
CHCH44 6060
HH22CC CHCH22
HCHC CHCH 26
AcetyleneAcetylene
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QuestionQuestion
Which one of the following is the strongest acid?
A) water
B) ammonia
C) 1-butene
D) 1-butyne
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CC HH HH++ ++
HH++ ++
HH++ ++
1010-60-60
1010-45-45
1010-26-26
sp3CC :
sp2
sp
HH
CC CC
CC CC HH
CC CC
CC CC :
:
Electrons in an orbital with more Electrons in an orbital with more ss character are closer to the character are closer to the
nucleus and more strongly held.nucleus and more strongly held.
Carbon: Hybridization and ElectronegativityCarbon: Hybridization and Electronegativity
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QuestionQuestion
Which one of the following statements best explains the greater acidity of terminal alkynes (RCCH) compared with monosubstituted alkenes (RCH=CH2)?
A) The sp-hybridized carbons of the alkyne are less electronegative than the sp2 carbons of the alkene.B) The two bonds of the alkyne are better able to stabilize the negative charge of the anion by resonance.C) The sp-hybridized carbons of the alkyne are more electronegative than the sp2 carbons of the alkene.D) The question is incorrect - alkenes are more acidic
than alkynes.
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The stronger the acid, the weaker its conjugate base
top 252
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Solution: Use a stronger base. Sodium amideSolution: Use a stronger base. Sodium amideis a stronger base than sodium hydroxide.is a stronger base than sodium hydroxide.
NHNH33NaNaNHNH22 ++ HCHC CHCH NaCNaC CHCH ++
––HH22NN
....:: HH CC CHCH HH
....++ ++ CC CHCH::
––
stronger acidstronger acidppKKaa = 26 = 26
weaker acidweaker acidppKKaa = 36 = 36
Ammonia is a weaker acid than acetylene.Ammonia is a weaker acid than acetylene.The position of equilibrium lies to the right.The position of equilibrium lies to the right.
HH22NN
Sodium AcetylideSodium Acetylide
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QuestionQuestion
Which of the following bases is strong enough to completely deprotonate propyne?
A) NH3
B) CH3OH
C) NaNH2
D) NaOH
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Preparation of Various Alkynes Preparation of Various Alkynes
by alkylation reactions withby alkylation reactions with
Acetylide or Terminal AlkynesAcetylide or Terminal Alkynes
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Synthesis Using Acetylide Ions: Formation of C–C Bond
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H—C H—C C—HC—H
RR—C —C C—HC—H
RR—C —C C—C—RR
Alkylation of Acetylene and Terminal AlkynesAlkylation of Acetylene and Terminal Alkynes
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RR XXSSNN22
XX––::++CC––::H—C H—C C—RC—RH—C H—C ++
The alkylating agent is an alkyl halide, andThe alkylating agent is an alkyl halide, andthe reaction is nucleophilic substitution.the reaction is nucleophilic substitution.
The nucleophile is sodium acetylide or the The nucleophile is sodium acetylide or the sodium salt of a terminal (monosubstituted) sodium salt of a terminal (monosubstituted) alkyne.alkyne.
Alkylation of Acetylene and Terminal AlkynesAlkylation of Acetylene and Terminal Alkynes
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NaNHNaNH22
NHNH33
CHCH33CHCH22CHCH22CHCH22BrBr
(70-77%)(70-77%)
HCHC CHCH HCHC CCNaNa
HCHC CC CHCH22CHCH22CHCH22CHCH33
Example: Alkylation of AcetyleneExample: Alkylation of Acetylene
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QuestionQuestion
Which alkyl halide will react faster with the acetylide ion (HCCNa) in an SN2 reaction?
A) bromopropane
B) 2-bromopropane
C) tert-butyl iodide
D) 1-bromo-2-methylbutane
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NaNHNaNH22, NH, NH33
CHCH33BrBr
CCHH(CH(CH33))22CHCHCHCH22CC
CCNaNa(CH(CH33))22CHCHCHCH22CC
(81%)(81%)
C—CHC—CH33(CH(CH33))22CHCHCHCH22CC
Example: Alkylation of a Terminal AlkyneExample: Alkylation of a Terminal Alkyne
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1. NaNH1. NaNH22, NH, NH33
2. 2. CHCH33CHCH22BrBr
(81%)(81%)
H—C H—C C—HC—H
1. NaNH1. NaNH22, NH, NH33
2. 2. CHCH33BrBr
C—HC—HCHCH33CHCH22—C—C
C—C—CHCH33CHCH33CHCH22—C—C
Example: Dialkylation of AcetyleneExample: Dialkylation of Acetylene
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Effective only with primary alkyl halidesEffective only with primary alkyl halides
Secondary and tertiary alkyl halides Secondary and tertiary alkyl halides undergo eliminationundergo elimination
LimitationLimitation
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E2 predominates over SE2 predominates over SNN2 when alkyl 2 when alkyl
halide is secondary or tertiary.halide is secondary or tertiary.
CC––::H—C H—C
E2E2
++CCH—C H—C ——HH CC CC XX––::++
Acetylide Ion as a BaseAcetylide Ion as a Base
HH CC
CC XX
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QuestionQuestion
Consider the reaction of each of the following with cyclohexyl bromide. For which one is
the ratio of substitution to elimination highest?
A) NaOCH2CH3, ethanol, 60°C
B) NaSCH2CH3, ethanol-water, 25°C
C) NaNH2, NH3, -33°C
D) NaCCH, NH3, -33°C
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Preparation of AlkynesPreparation of Alkynes
by Elimination Reactionsby Elimination Reactions
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Geminal dihalideGeminal dihalide Vicinal dihalideVicinal dihalide
XX
CC CC
XX
HH
HH
XX XX
CC CC
HHHH
The most frequent applications are in preparation The most frequent applications are in preparation of terminal alkynes.of terminal alkynes.
Preparation of AlkynesPreparation of Alkynesby "Double Dehydrohalogenation"by "Double Dehydrohalogenation"
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(CH(CH33))33CCCCHH22—CH—CHClCl22
1. 3NaNH1. 3NaNH22, NH, NH33
2. H2. H22OO
(56-60%)(56-60%)
(CH(CH33))33CCCC CHCH
Geminal dihalide Geminal dihalide Alkyne Alkyne
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NaNHNaNH22, NH, NH33
HH22OO
(CH(CH33))33CCCCHH22—CH—CHClCl22
(CH(CH33))33CCCCHH CHCHClCl(slow)(slow)
NaNHNaNH22, NH, NH33
(CH(CH33))33CCCC CHCH
(slow)(slow)
NaNHNaNH22, NH, NH33
(CH(CH33))33CCCC CNaCNa(fast)(fast)
Geminal dihalide Geminal dihalide Alkyne Alkyne
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Question Question
In addition to NaNH2, what other base can be
used to convert 1,1-dichlorobutane into
1-butyne?
A) NaOCH3
B) NaOH
C) NaOCH2CH3
D) KOC(CH3)3
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CHCH33(CH(CH22))77CCHH—C—CHH22BrBr
BrBr
1. 3NaNH1. 3NaNH22, NH, NH33
2. H2. H22OO
(54%)(54%)
CHCH33(CH(CH22))77CC CHCH
Vicinal dihalide Vicinal dihalide Alkyne Alkyne
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QuestionQuestion
Which of the following compounds yield 1-heptyne on being treated with three moles of sodium amide (in liquid ammonia as the solvent) followed by adding water to the reaction mixture?
A) 1,1,2,2-tetrachloroheptaneB) 1-bromo-2-chloroheptaneC) 1,1,2-trichloropentaneD) all of the above
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Reactions of AlkynesReactions of Alkynes
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Acidity Acidity
Hydrogenation Hydrogenation
Metal-Ammonia Reduction Metal-Ammonia Reduction
Addition of Hydrogen HalidesAddition of Hydrogen Halides
HydrationHydration
Addition of HalogensAddition of Halogens
OzonolysisOzonolysis
Reactions of AlkynesReactions of Alkynes
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Hydrogenation of Alkynes Hydrogenation of Alkynes
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Atomic Force Microscopy of Acetylene Lawrence Berkeley Laboratory (LBL)
C
C
H
H
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C
C
H
H
Calculated image (Philippe Sautet)
orbital
pz
TIP
H
O+
Imaging: acetylene on Pd(111) at 28 K
Molecular Image Tip cruising altitude ~700 pmΔz = 20 pm
Surface atomic profile
Tip cruising altitude ~500 pm
Δz = 2 pm
1 cm(± 1 μm)
The STM image is a map of the pi-orbital of distorted acetylene
Why don’t we see the Pd atoms?Because the tip needs to be very close to image the Pd atoms and would knock the molecule away
If the tip was made as big as an airplane, it would be flying at 1 cm from the surface and waving up an down by 1 micrometer
M. Salmeron (LBL)
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Excitation of frustrated rotational modes in acetylene molecules on Pd(111) at T = 30 K
Tip
e-
((( ) ( )))
M. Salmeron (LBL)
QuickTime™ and aYUV420 codec decompressorare needed to see this picture.
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RCRCHH22CCHH22R'R'catcat
catalyst = Pt, Pd, Ni, or Rhcatalyst = Pt, Pd, Ni, or Rh
alkene is an intermediatealkene is an intermediate
RCRC CR'CR' ++ 22HH22
Hydrogenation of AlkynesHydrogenation of Alkynes
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RCHRCH22CHCH22R'R'
Alkenes could be used to prepare alkenes if aAlkenes could be used to prepare alkenes if acatalyst were available that is active enough to catalyst were available that is active enough to catalyze the hydrogenation of alkynes, but notcatalyze the hydrogenation of alkynes, but notactive enough for the hydrogenation of alkenes.active enough for the hydrogenation of alkenes.
catcat
HH22
RCRC CR'CR'catcat
HH22
RCHRCH CHR'CHR'
Partial HydrogenationPartial Hydrogenation
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There is a catalyst that will catalyze the hydrogenationThere is a catalyst that will catalyze the hydrogenation
of alkynes to alkenes, but not that of alkenes to alkanes.of alkynes to alkenes, but not that of alkenes to alkanes.
It is called the Lindlar catalyst and consists ofIt is called the Lindlar catalyst and consists ofpalladium supported on CaCOpalladium supported on CaCO33, which has been , which has been
poisoned with lead acetate and quinoline.poisoned with lead acetate and quinoline.
synsyn-Hydrogenation occurs; cis alkenes are formed.-Hydrogenation occurs; cis alkenes are formed.
RCHRCH22CHCH22R'R'catcat
HH22
RCRC CR'CR'catcat
HH22
RCHRCH CHR'CHR'
Lindlar PalladiumLindlar Palladium
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+ + H H22
Lindlar PdLindlar Pd
CHCH33(CH(CH22))33 (CH(CH22))33CHCH33
HH HH
(87%)(87%)
CHCH33(CH(CH22))33CC C(CHC(CH22))33CHCH33
CCCC
ExampleExample
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Alkynes Alkynes transtrans-Alkenes-Alkenes
Metal-Ammonia ReductionMetal-Ammonia Reduction
of Alkynesof Alkynes
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RCHRCH22CHCH22R'R'
Another way to convert alkynes to alkenes isAnother way to convert alkynes to alkenes is
by reduction with sodium (or lithium or potassium)by reduction with sodium (or lithium or potassium)
in ammonia.in ammonia.
transtrans-Alkenes are formed.-Alkenes are formed.
RCRC CR'CR' RCHRCH CHR'CHR'
Partial ReductionPartial Reduction
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CHCH33CHCH22
CHCH22CHCH33HH
HH
(82%)(82%)
CHCH33CHCH22CC CCHCCH22CHCH33
CCCC
Na, NHNa, NH33
ExampleExample
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QuestionQuestion
How would you accomplish the following How would you accomplish the following conversion?conversion?
A)A) NaNHNaNH22
B)B) HH22, Lindlar Pd, Lindlar Pd
C)C) Na, NHNa, NH33
D)D) either B or Ceither B or C
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four stepsfour steps
(1)(1) electron transferelectron transfer
(2)(2) proton transferproton transfer
(3)(3) electron transferelectron transfer
(4)(4) proton transferproton transfer
Metal (Li, Na, K) is reducing agent; Metal (Li, Na, K) is reducing agent; HH22 is not involved; proton comes from NH is not involved; proton comes from NH33
MechanismMechanism
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QuestionQuestion
Select the most effective way to synthesize Select the most effective way to synthesize ciscis--2-pentene from 1-propyne.2-pentene from 1-propyne.
A)A) 1) NaNH1) NaNH22 2) CH 2) CH33CHCH22Br 3) HBr 3) H22, Pd, Pd
B)B) 1) NaNH1) NaNH22 2) CH 2) CH33Br 3) HBr 3) H22, Lindlar Pd, Lindlar Pd
C)C) 1) NaNH1) NaNH22 2) CH 2) CH33CHCH22I 3) HI 3) H22, Lindlar , Lindlar
PdPd
D)D) 1) NaNH1) NaNH22 2) CH 2) CH33CHCH22Br 3) Na,NHBr 3) Na,NH33
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AnswerAnswer
Select the most effective way to synthesize Select the most effective way to synthesize ciscis--2-pentene from 1-propyne.2-pentene from 1-propyne.
A)A) 1) NaNH1) NaNH22 2) CH 2) CH33CHCH22Br 3) HBr 3) H22, Pd, Pd
B)B) 1) NaNH1) NaNH22 2) CH 2) CH33Br 3) HBr 3) H22, Lindlar Pd, Lindlar Pd
C)C) 1) NaNH1) NaNH22 2) CH 2) CH33CHCH22I 3) HI 3) H22, Lindlar , Lindlar
PdPd
D)D) 1) NaNH1) NaNH22 2) CH 2) CH33CHCH22Br 3) Na,NHBr 3) Na,NH33
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QuestionQuestion
Which reagent would accomplish the Which reagent would accomplish the transformation of 3-hexyne into transformation of 3-hexyne into transtrans-3--3-hexene?hexene?
A)A) HH22/Ni/Ni
B)B) HH22, Lindlar Pd, Lindlar Pd
C)C) Na, NHNa, NH33
D)D) NaNHNaNH22, NH, NH33
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AnswerAnswer
Which reagent would accomplish the Which reagent would accomplish the transformation of 3-hexyne into transformation of 3-hexyne into transtrans-3--3-hexene?hexene?
A)A) HH22/Ni/Ni
B)B) HH22, Lindlar Pd, Lindlar Pd
C)C) Na, NHNa, NH33
D)D) NaNHNaNH22, NH, NH33
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Suggest an efficient syntheses of (Suggest an efficient syntheses of (EE)- and ()- and (ZZ)-2-)-2-heptene from propyne and any necessary organicheptene from propyne and any necessary organic or inorganic reagents. or inorganic reagents.
ProblemProblem
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Problem Problem StrategyStrategy
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Problem Problem StrategyStrategy
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1. NaNH1. NaNH22
2. CH2. CH33CHCH22CHCH22CHCH22BrBr
Na, NHNa, NH33HH22, Lindlar Pd, Lindlar Pd
Problem Problem SynthesisSynthesis
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Question Question
Which would be the best sequence of reactions to use in order to prepare cis-3-nonenefrom 1-butyne?
A) 1. NaNH2 in NH3; 2. 1-bromopentane; 3. H2, Lindlar Pd
B) 1. NaNH2 in NH3; 2. 1-bromopentane; 3. Na, NH3
C) 1. H2, Lindlar Pd; 2. NaNH2 in NH3; 3. 1-bromopentane
D) 1. Na, NH3; 2. NaNH2 in NH3; 3. 1-bromopentane
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Addition of Hydrogen HalidesAddition of Hydrogen Halides
to Alkynesto Alkynes
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HBrHBr
BrBr
(60%)(60%)
Alkynes are slightly less reactive than alkenesAlkynes are slightly less reactive than alkenes
CHCH33(CH(CH22))33CC CHCH CHCH33(CH(CH22))33CC CHCH22
Follows Markovnikov's RuleFollows Markovnikov's Rule
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(76%)(76%)
CHCH33CHCH22CC CCHCCH22CHCH33
2 H2 HFF
FF
FF
CC CC
HH
HH
CHCH33CHCH22 CHCH22CHCH33
Two Molar Equivalents of Hydrogen HalideTwo Molar Equivalents of Hydrogen Halide
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HBrHBr
(79%)(79%)
regioselectivity opposite to Markovnikov's ruleregioselectivity opposite to Markovnikov's rule
CHCH33(CH(CH22))33CC CHCH CHCH33(CH(CH22))33CCHH CHCHBrBrperoxidesperoxides
Free-radical Addition of HBrFree-radical Addition of HBr
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expected reaction:expected reaction:
enolenolobserved reaction:observed reaction:
RCHRCH22CR'CR'
OO
HH++
RCRC CR'CR' HH22OO++
HH++
RCRC CR'CR' HH22OO++
OHOH
RCHRCH CR'CR'
ketoneketone
Hydration of AlkynesHydration of Alkynes
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enols are regioisomers of ketones, and exist enols are regioisomers of ketones, and exist in equilibrium with themin equilibrium with them
keto-enol equilibration is rapid in acidic mediaketo-enol equilibration is rapid in acidic media
ketones are more stable than enols andketones are more stable than enols andpredominate at equilibriumpredominate at equilibrium
enolenol
OHOH
RCHRCH CR'CR' RCHRCH22CR'CR'
OO
ketoneketone
EnolsEnols
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OO HH
CC CC
HH++OO
HH
HH
::
....::
Mechanism of conversion of enol to ketoneMechanism of conversion of enol to ketone
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OO HH
CC CC
HH++OO
HH
HH
::
....::
Mechanism of conversion of enol to ketoneMechanism of conversion of enol to ketone
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OO HH
CC CCHH++
OO
HH
HH
::
....::
::
Mechanism of conversion of enol to ketoneMechanism of conversion of enol to ketone
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OO HH
CC CC
HH
HH
OO:: ::
HH++
....::
Mechanism of conversion of enol to ketoneMechanism of conversion of enol to ketone
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Carbocation is stabilized by Carbocation is stabilized by electron delocalization (resonance).electron delocalization (resonance).
HH OO
CC CCHH
....HH++
Key Carbocation IntermediateKey Carbocation Intermediate
OO
CC CCHH++
....::
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OO HH
CC CC
HH
HH
OO:: ::
HH++
....::
Mechanism of conversion of enol to ketoneMechanism of conversion of enol to ketone
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Useful for symmetrical starting alkynesUseful for symmetrical starting alkynes
to produce a single product.to produce a single product.
Unsymmetrical starting alkynes that are Unsymmetrical starting alkynes that are not terminal produce a mixture of not terminal produce a mixture of ketones…non-regioselectively.ketones…non-regioselectively.
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HH22O, HO, H22SOSO44
HgSOHgSO44
CHCH33(CH(CH22))55CCHCCH33
(91%)(91%)viavia
Markovnikov's rule followed in formation of enol, Markovnikov's rule followed in formation of enol, Useful with terminal alkynes. Useful with terminal alkynes.
CHCH33(CH(CH22))55CC CHCH22
OHOH
CHCH33(CH(CH22))55CC CHCH
OO
RegioselectivityRegioselectivity
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Aldehyde vs. Ketone
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QuestionQuestion
What is the product of the acid catalyzed What is the product of the acid catalyzed hydration of 1-hexyne?hydration of 1-hexyne?
A) A) B)B)
C)C) D)D)
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Addition of Halogens to AlkynesAddition of Halogens to Alkynes
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+ 2 + 2 ClCl22
ClCl
ClCl
(63%)(63%)
CCClCl22CHCH CHCH33HCHC CCHCCH33
ExampleExample
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BrBr22
CHCH33CHCH22
CHCH22CHCH33BrBr
BrBr
(90%)(90%)
CHCH33CHCH22CC CCHCCH22CHCH33 CC CC
Addition is antiAddition is anti
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gives two carboxylic acids by cleavage gives two carboxylic acids by cleavage of triple bondof triple bond
Ozonolysis of AlkynesOzonolysis of Alkynes
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1. 1. OO33
2. H2. H22OO
CHCH33(CH(CH22))33CC CCHH
++CHCH33(CH(CH22))33CCOHOH
(51%)(51%)
OO
HOHOCCOHOH
OO
ExampleExample
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QuestionQuestion
What product is formed when 2-butyne is What product is formed when 2-butyne is subjected to ozonolysis?subjected to ozonolysis?
A)A) B)B)
C)C) D)D)
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AlkynesAlkynes
Synthesis & FunctionsSynthesis & Functions
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Can you identify and name the function?Can you identify and name the function?
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Example
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Question Question
What is the structure of What is the structure of Compound YCompound Y in the in the following synthetic sequence? following synthetic sequence?
A)A) pentanepentane
B)B) ciscis-2-pentene-2-pentene
C)C) transtrans-2-pentene-2-pentene
D)D) 2-pentyne2-pentyne