alkenes and alkynes chapter #3
DESCRIPTION
Alkenes and Alkynes Chapter #3. Alkene Introduction. Hydrocarbon with carbon-carbon double bonds Sometimes called olefins , “oil-forming gas” General formula C n H 2n n≥2 Examples n=2 C 2 H 4. Common Names. Usually used for small molecules. Examples:. CH 3. - PowerPoint PPT PresentationTRANSCRIPT
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Alkenes and AlkynesChapter #3
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Alkene Introduction• Hydrocarbon with carbon-carbon double bonds• Sometimes called olefins, “oil-forming gas”• General formula CnH2n n≥2• Examples
n=2 C2H4
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Common NamesUsually used for small molecules.Examples:
Vinyl carbons are the carbons sharing a double bond in blue
Vinyl hydrogens are the hydrogens bonded to vinyl carbons in red
CH2=CH2 CH2=CH-CH3 CH2=C-CH3
ethylene propylene isobutylene
CH3
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IUPAC Nomenclature
• Parent is longest chain containing the double or triple bond.• -ane changes to –ene (or -diene, -triene) for double bonds, or –yne (or –diyne, -triyne).• Number the chain so that the double bond, or triple bond has the lowest possible number.• In a ring, the double bond is assumed to be between carbon 1 and carbon 2.
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Name These Alkenes
CH2 CH CH2 CH3
CH3 C
CH3
CH CH3
CH3
CHCH2CH3H3C
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Name These Alkenes
CH2 CH CH2 CH3
CH3 C
CH3
CH CH3
CH3
CHCH2CH3H3C1-butene
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Name These Alkenes
CH2 CH CH2 CH3
CH3 C
CH3
CH CH3
CH3
CHCH2CH3H3C
1-butene
2-methyl-2-butene
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Name These Alkenes
CH2 CH CH2 CH3
CH3 C
CH3
CH CH3
CH3
CHCH2CH3H3C
1-butene
2-methyl-2-butene
3-methylcyclopentene
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Name These Alkenes
CH2 CH CH2 CH3
CH3 C
CH3
CH CH3
CH3
CHCH2CH3H3C
1-butene
2-methyl-2-butene
3-methylcyclopentene
2-sec-butyl-1,3-cyclohexadiene
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Name These Alkenes
CH2 CH CH2 CH3
CH3 C
CH3
CH CH3
CH3
CHCH2CH3H3C
1-butene
2-methyl-2-butene
3-methylcyclopentene
2-sec-butyl-1,3-cyclohexadiene
3-n-propyl-1-heptene
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Alkene Substituents= CH2
methylene
- CH = CH2
vinyl
- CH2 - CH = CH2
allyl
- CH2 - CH = CH2
allyl
Name = ?
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Alkene Substituents= CH2
methylene
- CH = CH2
vinyl
- CH2 - CH = CH2
allyl
- CH2 - CH = CH2
allyl
Name = Methylenecyclohexane Name =
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Alkene Substituents= CH2
methylene
- CH = CH2
vinyl
- CH2 - CH = CH2
allyl
Name = Methylenecyclohexane Name = vinylcyclohexane
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Alkyne Common Names
• Acetylene is the common name for the two carbon alkyne.
• To give common names to alkynes having more than two carbons, give alkyl names to the carbon groups attached to the vinyl carbons followed by acetylene.
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Alkyne Examples
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Alkyne Examples
Isopropyl methyl acetylene
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Alkyne Examples
Isopropyl methyl acetylene sec-butyl Cyclopropyl acetylene
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Cis-trans Isomerism• Similar groups on same side of double bond, alkene is cis.
• Similar groups on opposite sides of double bond, alkene is trans.
• Cycloalkenes are assumed to be cis.
• Trans cycloalkenes are not stable unless the ring has at least 8 carbons.
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Name these:
C CCH3
H
H
CH3CH2
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Name these:
C CCH3
H
H
CH3CH2
trans-2-pentene
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Name these:
C CCH3
H
H
CH3CH2
trans-2-pentene
C CBr
H
Br
H
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Name these:
C CCH3
H
H
CH3CH2
trans-2-pentene
C CBr
H
Br
H
cis-1,2-dibromoethene
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Which of the following show cis/trans isomers?
a. 1-penteneb. 2-pentenec. 1-chloro-1-pentened. 2-chloro-1-pentenee. 2-chloro-2-pentene
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Solution to the Question
H
H
H
Hydrogens cannon be both cis and trans. Reversing the hydrogens on the first carbon produces the same compound.
H
H
H
1-Pentene
H
2-Pentene does show cis/trans isomerism
H
H
2-Pentene
H
H
1-Chloro-1-pentene does show cis/trans isomerism
H
1-chloro-1-pentene
Cl
H
H
Cl cis trans
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Solution to the QuestionCl
2-Chloro-1-pentene does not show cis/trans isomerism, since flipping the hydrogen atoms in C-1 produces the same compound
Cl
2-chloro-1-pentene
H
H
H
H
Cl
2-Chloro-2-pentene does show cis/trans isomerism, since since the colored atoms on the vinyl carbons are on the same side in cis and opposite sides on the trans isomer.
Cl
2-chloro-2-pentene
H
Htrans cis
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Which of the following show cis/trans isomers?
a. 1-pentene-Nob. 2-pentene- Yesc. 1-chloro-1-pentene- Yesd. 2-chloro-1-pentene- Noe. 2-chloro-2-pentene- yes
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E-Z Nomenclature• Use the Cahn-Ingold-Prelog rules to assign priorities to groups attached to each carbon in the double bond. Highest priority is #1 and is the element with the largest atomic number.• If high priority groups are on the same side, the name is Z (for zusammen).• If high priority groups are on opposite sides, the name is E (for entgegen).
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Example, E-Z
C C
H3C
H
Cl
CH2C C
H
H
CH CH3
Cl1
2
1
2
2
1
1
2
2Z 5E
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Example, E-Z
C C
H3C
H
Cl
CH2C C
H
H
CH CH3
Cl1
2
1
2
2
1
1
2
2Z 5E
3,7-dichloro-(2Z, 5E)-2,5-octadiene
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Physical Properties• Low boiling points, increasing with mass.
• Branched alkenes have lower boiling points.
• Less dense than water.
•Nonpolar (Hydrophobic)
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Alkene Synthesis
• Dehydrohalogenation (-HX)• Dehydration of alcohols (-H2O)
OHH + H2O
minor major
Examples:Cl
NaOHminor major
+ + + NaCl + HOH
Zaitsev’s rule: The major product contains the most substituted double bond
Elimination Reactions:
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Alkene ReactionsI. Addition Reactions
C=C
a. Hydration
C-C+ H-O-H
C=C
C=C
H O-H
b. Hydrogenation
C-C+ H-H
HH
c. Halogenation
+ X-X
Catalyst
H+
Catalyst = Ni, Pt, Pd
C-C
X X
Alcohol
Alkane
X = Cl, Br, IDihalide
Follows Markovnikov’s Rule
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RegiospecificityMarkovnikov’s Rule: The proton (H+) of an acid adds to the carbon in the double bond that already has the most H’s. “Rich get richer.”
C=C
Examples:
CH3H
H
HH
C=CH CH3
H
+ H-O-HH+
+ H-Cl
H
C-CH
H Cl
H
H
C-CH
H O-H
H
CH3
CH3Major Products
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Alkene Reactions (2)I. Addition Reactions (cont.)
d. Hydrohalogenation
C=C C-C+ H-X
C=C
H X
e. Glycol Formation
+ H-O-O-H C-C
H-O O-H
Alkyl halide
Glycol
Follows Markovnikov’s Rule
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Alkene ReactionsStep 1: Pi electrons attack the electrophile.
Step 2: Nucleophile attacks the carbocation
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Terpenes• Composed of 5-carbon isopentyl groups.• Isolated from plants’ essential oils.• C:H ratio of 5:8, or close to that.• Pleasant taste or fragrant aroma.• Examples:
Myrcene (From bay or myrcia plants)α-Pinene (From pine trees)Β-Selinene (From celery)Menthol (From peppermint oil)Camphor (From evergreen trees)R-Carvone (From spearmint)
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Classification
• Terpenes are classified by the number of carbons they contain, in groups of 10.• A monoterpene has 10 C’s, 2 isoprenes. • A diterpene has 20 C’s, 4 isoprenes.• A sesquiterpene has 15 C’s, 3 isoprenes.
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Terpenes
2-methyl-1,3-butadieneIsoprene
headtail
head
tail
head
Geraniol (roses)Head to tail link of two isoprenesCalled diterpene
OH
head
tail
head
tail
Menthol (pepermint)Head to tail link of two isoprenes another diterpene
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Structure of Terpenes
Two or more isoprene units, 2-methyl-1,3-butadiene with some modification of the double bonds.
myrcene, frombay leaves
oCamphor (monoterpene)
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ALKENE REVIEW
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Describe the geometry around the carbon–carbon double bond.
a. Tetrahedralb.Trigonal pyramidalc. Trigonal planard.Bente.Linear
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Answer
a. Tetrahedralb.Trigonal pyramidalc. Trigonal planard.Bente.Linear
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Give the formula for an alkene.
a. CnH2n-4
b.CnH2n-2
c. CnH2n
d.CnH2n+2
e.CnH2n+4
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Answer
a. CnH2n-4
b.CnH2n-2
c. CnH2n
d.CnH2n+2
e.CnH2n+4
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Name CH3CH=CHCH=CH2.
a. 2,4-butadieneb.1,3-butadienec. 2,4-pentadiened.1,3-pentadienee.1,4-pentadiene
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Answer
a. 2,4-butadieneb.1,3-butadienec. 2,4-pentadiened.1,3-pentadienee.1,4-pentadiene
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Calculate the unsaturation number for C6H10BrCl.
a. 0b.1c. 2d.3
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Answer
a. 0b.1c. 2d.3
U = 0.5 [2(6) + 2 – (12)] = 1
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Name .
a. Trans-2-penteneb. Cis-2-pentenec. Trans-3-methyl-2-pentened. Cis-3-methyl-2-pentene
CC
H
H3C CH3
CH2CH3
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Name
a. Trans-2-penteneb. Cis-2-pentenec. Trans-3-methyl-2-pentened. Cis-3-methyl-2-pentene
CC
H
H3C CH3
CH2CH3
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Name
a. E-2-penteneb. Z-2-pentenec. E-3-methyl-2-pentened. Z-3-methyl-2-pentenee. Z-2-methyl-2-pentene
CC
H
H3C CH3
CH2CH3
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Name
a. E-2-penteneb. Z-2-pentenec. E-3-methyl-2-pentened. Z-3-methyl-2-pentenee. Z-2-methyl-2-pentene
CC
H
H3C CH3
CH2CH3
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a. ClCH2CH2Cl
b.ClCH=CHClc. CH2=CH2
d.CH2=CHCl
CC
H
H H
H
Cl2 NaOH
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Answer
a. ClCH2CH2Cl
b.ClCH=CHClc. CH2=CH2
d.CH2=CHCl
Chlorine is added across the double bond, then HCl is lost.
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a. (CH3)2CHOH
b.CH3CH2CH2OH
c. HOCH2CH2CH2OH
d.CH3CH(OH)CH2OH
CC
H
H CH3
H
H2O
catalyst
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Answer
a. (CH3)2CHOH
b.CH3CH2CH2OH
c. HOCH2CH2CH2OH
d.CH3CH(OH)CH2OH
Water adds by Markovnikov’s orientation across the double bond.
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Identify the product formed from the polymerization of tetrafluoroethylene.
a. Polypropyleneb.Poly(vinyl chloride), (PVC)c. Polyethylened.Poly(tetrafluoroethylene), Teflon
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Answer
a. Polypropyleneb.Poly(vinyl chloride), (PVC)c. Polyethylened.Poly(tetrafluoroethylene), Teflon
Teflon is formed from the polymerization of tetrafluoroethylene.
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a. CH3CCCH3
b.CH2=CHCH=CH2
c. CH3CH=CHCH3
d.CH3CH2CH2CH3
CC
H
H3C CH3
H
H2
Pd
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Answer
a. CH3CCCH3
b.CH2=CHCH=CH2
c. CH3CH=CHCH3
d.CH3CH2CH2CH3
Hydrogen adds across the double bond to form an alkane.
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a. (CH3)2CHOSO3H
b.CH3CH=CH2
c. (CH3)2C=O
d.CH3CH2COOH
HCH3C
OH
CH3
H2SO4
heat
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7.15 Answer
a. (CH3)2CHOSO3H
b.CH3CH=CH2
c. (CH3)2C=O
d.CH3CH2COOH
Acid dehydrates alcohols to form alkenes.
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Give the products from the catalytic cracking of alkanes.
a. Alkanesb.Alkenesc. Alkynesd.Alkanes + alkenese.Alkanes + alkynes
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Answer
a. Alkanesb.Alkenesc. Alkynesd.Alkanes + alkenese.Alkanes + alkynes
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Give the products from the dehydrogenation of alkanes.
a. Alkanesb.Alkenesc. Alkynesd.Alkanes + alkenese.Alkanes + alkynes
![Page 66: Alkenes and Alkynes Chapter #3](https://reader033.vdocuments.net/reader033/viewer/2022061610/56813fd0550346895daab188/html5/thumbnails/66.jpg)
Give the products from the dehydrogenation of alkanes.
a. Alkanesb.Alkenesc. Alkynesd.Alkanes + alkenese.Alkanes + alkynes
![Page 67: Alkenes and Alkynes Chapter #3](https://reader033.vdocuments.net/reader033/viewer/2022061610/56813fd0550346895daab188/html5/thumbnails/67.jpg)
End Chapter #3