Reactions and Reagent Structures of Chp. 16

Important: 
* IDENTIFICATION method; causes decolorization, but SLOWLY
* SUBSTITUTION not addition
* all THREE double bonds are retained
* only works with BROMINE
Important:
* IDENTIFICATION method; causes decolorization, but SLOWLY
* SUBSTITUTION not addition
* all THREE double bonds are retained
* only works with BROMINE
benzene + bromine + carbon tetracholoride + ferric bromide –> hyrobromic acid (gas) + bromobenzene
Important: 
* NO decolorization (red to clear)
Important:
* NO decolorization (red to clear)
benzene + bromine + carbon tetrachloride –> no reaction
Important: 
* NO decolorization (purple to brown)
Important:
* NO decolorization (purple to brown)
benzene + potassium permanganate + water –> no reaction
Name the compound (it has two names).
Name the compound (it has two names).
ferric bromide
iron (III) bromide
Important: 
* requires MORE ACTIVE CATALYST than just Pt, Pd, etc.
* requires HIGHER PRESSURES of H2
* ∆H < ∆Hº of conjugated DIENE; resonance energy/double bond is amazingly low
Important:
* requires MORE ACTIVE CATALYST than just Pt, Pd, etc.
* requires HIGHER PRESSURES of H2
* ∆H < ∆Hº of conjugated DIENE; resonance energy/double bond is amazingly low
catalytic hydrogenation of benzene
benzene + 3H2 –> cyclohexane
Important:
* occurs by extremely FAST DIELS-ALDER reaction
* reason why cyclobutadiene has NEVER been isolated and purified
Important:
* occurs by extremely FAST DIELS-ALDER reaction
* reason why cyclobutadiene has NEVER been isolated and purified
dimerization of cyclobutadiene monomer
Name the annulene.
Name the annulene.
[4]annulene
cyclobutadiene
Name the annulene compound.
Name the annulene compound.
[8]annulene
cyclooctatetraene
Name the annulene shown in the picture.
Name the annulene shown in the picture.
[10]annulene
cyclodecapentaene
Draw phenylalanine.
Draw phenylalanine.
Name the aliphatic polyene.
Name the aliphatic polyene.
hexa-1,3,5-triene
Name the aliphatic polyene shown in the picture.
Name the aliphatic polyene shown in the picture.
buta-1,3-diene
Draw and name the acyclic counterpart of cyclohexa-1,3-diene.
Draw and name the acyclic counterpart of cyclohexa-1,3-diene.
cis,cis-hexa-2,4-diene
Give BOTH names of the cyclic polyene shown in its two most common conformations.
Give BOTH names of the cyclic polyene shown in its two most common conformations.
cyclotetradecaheptaene
[14]annulene
LEFT: antiaromatic
RIGHT: aromatic
Name the polycyclic compound.
Name the polycyclic compound.
pyrene
Name the aromatic polycylic compound.
Name the aromatic polycylic compound.
napthalene (C10H8)
IMPORTANT:
* simplest poylnuclear aromatic hydrocarbon (PAH or PNA)
* lower resonance energy than benzene
* 10 electrons in resonance system
* has three Kekulé structures
* MOTHBALLS
Give BOTH names of the cyclic polyene shown in four of its conformations.
Give BOTH names of the cyclic polyene shown in four of its conformations.
cyclodecapentaene
[10]annulene
Give two names for the compound shown.
Give two names for the compound shown.
cyclooctadecanonaene
[18]annulene
Give the name of the molecule.
Give the name of the molecule.
heptalene
Give the name of the molecule in the image.
Give the name of the molecule in the image.
azulene (an constitutional isomer of naphthalene)
Give the name of the compound in the image.
Give the name of the compound in the image.
pentalene
IMPORTANT:
* cyclopentadiene has a pKa of 16, near that of water!
* must use a really strong base (hydroxide ion wouldn't deprotonate because water is a stronger acid)
* note how the cyclopentadienyl anion can be written in shorthand
IMPORTANT:
* cyclopentadiene has a pKa of 16, near that of water!
* must use a really strong base (hydroxide ion wouldn’t deprotonate because water is a stronger acid)
* note how the cyclopentadienyl anion can be written in shorthand
cyclopentadiene + tert-butoxide ion –> tert-butanol + cyclopentadienyl anion (aromatic)
IMPORTANT:
* the cyclopenta-2,4-dien-1-ol cation is too unstable for the hydronium to act as a leaving group because the ion is antiaromatic
IMPORTANT:
* the cyclopenta-2,4-dien-1-ol cation is too unstable for the hydronium to act as a leaving group because the ion is antiaromatic
cyclopenta-2,4-dien-1-ol + conc. H2SO4 –> protonated cyclopenta-2,4-dien-1-ol [FINAL PRODUCT]
Name the cation; it has two names.
Name the cation; it has two names.
tropylium ion
cycloheptatrienyl cation
IMPORTANT:
* the tropylium ion is a more stable base than the hydroxide ion
IMPORTANT:
* the tropylium ion is a more stable base than the hydroxide ion
cycloheptatrienol + aqueous solution of pH<3 --> tropylium ion
IMPORTANT:
* sp3 hydrogen taken
* reaction not favored 
* barely more acidic than propene
* gains only one electron
IMPORTANT:
* sp3 hydrogen taken
* reaction not favored
* barely more acidic than propene
* gains only one electron
cycloheptatriene + very strong base –> cycloheptatrienyl anion + B-H
IMPORTANT:
* forms a hydrocarbon dianion (rare)
* cyclooctatetraene gains TWO electrons via the reaction
* the hydrogens leave and do not retain any electrons
* potassium donates two electrons to the hydrogen cations
IMPORTANT:
* forms a hydrocarbon dianion (rare)
* cyclooctatetraene gains TWO electrons via the reaction
* the hydrogens leave and do not retain any electrons
* potassium donates two electrons to the hydrogen cations
cyclooctatetraene + 2 potassium metal –> cyclooctatetranyl DIANION + 2K+ + H2 (gas)
Draw the structure of pyridine.
Draw the structure of pyridine.
IMPORTANT:
* aromatic
* pKb = 8.8
* usually undergoes substitution rather than addition
Draw the pyridinium ion.
Draw the pyridinium ion.
IMPORTANT:
* It is still aromatic.
* pKa = 5.2
Draw the structure of pyrrole
Draw the structure of pyrrole
* pKb = 13.6
* strong acid usually protonates at C2
* when protonated at nitrogen, denoted “N-protonated pyrrole”
* N-protonated pyrrole pKa = 0.4
Draw the structure of pyrimidine.
Draw the structure of pyrimidine.
Draw the structure of pyrimidazole.
Draw the structure of pyrimidazole.
IMPORTANT:
* when imidazole becomes protonated, the nitrogens become chemically equivalent (isoelectronic) due to resonance
IMPORTANT:
* when imidazole becomes protonated, the nitrogens become chemically equivalent (isoelectronic) due to resonance
imidazole + acid –> protonated imidazole [resonance] <---> equilibrium
Draw the structure of purine.
Draw the structure of purine.
IMPORTANT:
* four nitrogens total
* three basic nitrogens
* one nonbasic nitrogen
* imidazole ring and pyrimidine ring fused together
Draw the structure of furan.
Draw the structure of furan.
IMPORTANT:
* once it’s hydrogenated, it’s known as tetrahydrofuran
* the oxygen atom is sp2 hybridized, with one lone pair in a 2p orbital and one lone pair in an sp2 orbital
* aromatic
Draw the structure of thiophene.
Draw the structure of thiophene.
IMPORTANT:
* also known as THIOFURAN
* sulfur is sp2 hybridized with one lone pair in a 3p orbital and the other lone pair in an sp2 orbital
* aromatic
Give both names of the compound shown.
Give both names of the compound shown.
ammonia
azane
Is the compound shown aromatic, nonaromatic, or antiaromatic?
Is the compound shown aromatic, nonaromatic, or antiaromatic?
Name the PAH.
Name the PAH.
anthracene (C14H10)
IMPORTANT:
* can undergo addition reactions
* 4 resonance structures
Name the PNA.
Name the PNA.
phenanthrene (C14H10)
* can undergo addition reactions
* 5 resonance structures
IMPORTANT:
* goes by 1,4-addition to maintain integrity of two isolated, aromatic benzene rings
IMPORTANT:
* goes by 1,4-addition to maintain integrity of two isolated, aromatic benzene rings
anthracene + Br2 in carbon tetrachloride (nonpolar solvent) –> 9,10-dibromo compound
IMPORTANT:
* goes by 1,2-addition to maintain integrity of two isolated, aromatic benzene rings
IMPORTANT:
* goes by 1,2-addition to maintain integrity of two isolated, aromatic benzene rings
phenanthrene + Br2 in carbon tetrachloride (nonpolar solvent) –> 9,10-dibromo compound
Name the large polynuclear aromatic hydrocarbon.
Name the large polynuclear aromatic hydrocarbon.
benzo[a]pyrene
IMPORTANT:
* one of the most thoroughly studied carcinogens
* found in cigarette smoke
* formed whenever organic compounds undergo incomplete combustion
* epoxides form and react with DNA
Name the six-ringed polynuclear aromatic hydrocarbon.
Name the six-ringed polynuclear aromatic hydrocarbon.
dibenzopyrene
pyrimidine + imidazole =
pyrimidine + imidazole =
purine
benzene + imidazole =
benzene + imidazole =
benzimidazole
benzene + pyrrole =
benzene + pyrrole =
indole
benzene + pyridine =
benzene + pyridine =
quinoline
benzene + furan =
benzene + furan =
benzofuran
benzene + thiophene =
benzene + thiophene =
benzothiophene
Please name the compound; give both its common name and IUPAC name.
Please name the compound; give both its common name and IUPAC name.
IMPORTANT: it’s found in licorice
Name the compound; give both its common name and IUPAC name.
Name the compound; give both its common name and IUPAC name.
IMPORTANT: it’s found in Maraschino cherries
Give three names for the compound.
Give three names for the compound.
propanone, dimethyl ketone, and acetone
Give both the common and IUPAC names for the compound.
Give both the common and IUPAC names for the compound.
Give the common name and the IUPAC name for the compound.
Give the common name and the IUPAC name for the compound.
Give both the common name and the IUPAC name for the compound.
Give both the common name and the IUPAC name for the compound.
Give the common and systematic names for the compound.
Give the common and systematic names for the compound.
Give both names for the compound.
Give both names for the compound.
Give both names for the compound shown.
Give both names for the compound shown.
Name the benzene derivative.
Name the benzene derivative.
Name the derivative of benzene.
Name the derivative of benzene.
Name the benzene derivative in the image.
Name the benzene derivative in the image.
Name the derivative of benzene in the image.
Name the derivative of benzene in the image.
Give two names for the compound.
Give two names for the compound.
Give two names for the compound in the picture.
Give two names for the compound in the picture.
Name the compound in the picture; it has two names.
Name the compound in the picture; it has two names.
three methyls + benzene
three methyls + benzene
mesitylene
1,3,5-trimethylbenzene
two methyls + benzene; meta positioning
two methyls + benzene; meta positioning
m-xylene
1,3-dimethylbenzene
one methyl + one hydroxy group + benzene; para positioning
one methyl + one hydroxy group + benzene; para positioning
p-cresol
4-methylphenol
toluene + acetyl group; ortho positioning
toluene + acetyl group; ortho positioning
o-toluic acid
2-methylbenzoic acid
Give four names for the compound, tricky little bastard.
Give four names for the compound, tricky little bastard.
benzyl ethyl ether
(ethoxymethyl)benzene
α-ethoxytoluene
benzoxyethane

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