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WGU-Organic Chem 12

Reactions, Part II

benzene an organic chemical compound with the molecular formula C6H6. It is sometimes abbreviated Ph–H. It is a colorless and highly flammable liquid with a sweet smell and a relatively high melting point
aromaticity chemical property in which a conjugated ring exhibit a stabilization stronger than would be expected by the stabilization of conjugation alone. It can also be considered a manifestation of cyclic delocalization and of resonance
huckel's rule A cyclic ring molecule follows this rule when the number of its π-electrons equals 4n+2 where n is zero or any positive integer
molecular orbital theory is a method for determining molecular structure in which electrons are not assigned to individual bonds between atoms, but are treated as moving under the influence of the nuclei in the whole molecule.
most characteristic aromatic compound reaction Electrophilic aromatic substitution or Ar-H in Halogenation, Nitration, Sulfonation, Alkylation, and Acylation reactions
three general steps to electrophilic aromatic substitution 1. Generation of electrophile(E+)2.Attack of electrophile on ring to give Carbocation intermediate(C+) 3. Proton transfer to a base(Base-H)
intermediate during chlorination and bromination of aromatic compounds resonance stablized cation intermediate where C+ moves around the ring and H + Cl bonded to same carbon of the ring
reagents for the nitration of benzene HNO3 with H2SO4 where the electrophile is NO2+ formed by treating HNO3 with H2SO4
reagents for the sulfonation of benzene H2SO4 where electrophile is HSO3+
why is the order for electrophilic substitution important because there are three isomeric products possible that may be ortho, meta, or para position to the first group substituted not only orientation is affected but so is the rate of further substitution
most activating substituents to further electrophilic aromatic substitution Ortho-Para(strongly activating)-NH2,-NHR,-NR2,-OH,-OR Meta(strongly deactivating)-NO2,-NH3+,-CF3,-CCl3
addition of grignard reagents in aldehydes and ketone grignard reagent R-MgBr + formaldehyde H(C=O)H in ether gives a magnesium alkoxide R-CH2(O-MgBr+) then reacts with HCl and H2O to create R-CH2OH(primary alcohol)plus Mg(2+)Other aldehydes create secondary alcohols and ketones create tertiary alcohols
grignard reagent a compound with a carbon-magnesium bromide bond or RMgBr
formaldehyde + grignard reagent plus hydrolysis in aqueous acid yields primary alcohol
carbonyl carbon + what makes hemiacetal alcohol oxygen adds to carbonyl carbon and Hydrogen adds to carbonyl oxygen
carbonyl oxygen + what makes hemiacetal alcohol oxygen adds to carbonyl carbon and Hydrogen adds to carbonyl oxygen
hemiacetal formation versus acetal formation acetal formation is done by excess alcohol used as reagent and solvent or by dehydration of H2O
addition of ammonia to aldehydes and ketone ammonia NH3 creates R-CH=NH and H2O
addition of amines to aldehydes and ketones creates an imine(Schiff base) and water where R-(C=O)H + H2N-R' create R-CH=N-R' plus H2O
addition of alpha-halogenation to aldehydes and ketones
common oxidizing agents for aldehydes to carboxylic acids chromic acid(H2CrO4),molecular oxygen(O2),Silver Ion(Ag2O with THF,H2O,NaOH),Tollens' reagent(AgNO3 H2O + NaOH to create Ag2O then add NH3 H2O to create Ag(NH3)2+NO3-, Hydrogen Peroxide(H2O2)
comman reactants and catalysts during a catalytic reduction of aldehydes and ketones into alcohols primary and secondary transition metal catalyst of Palladium, Platinum, nickel, or rhodium 25-100 degrees celsius and 1-5 atm pressure C=C are also reduced
comman reactants and catalysts during a metal hybride reduction NaBH4(only aldehydes and ketones carbonyl groups) and LiAlH4(also carboxylic acid carbonyl groups) Where H2 and Rh only do C=C solvent includes Ch3OH methanol CH3CH2OH ethanol
reagents used to oxidize aldehydes and ketones to carboxylic acids
reactants to reduce aldehydes and ketones to alcohols
reactants to oxidize alcohols to aldehydes and ketones
important characteristics of PCC pyridinium chlorchromate reagent during the oxidation of alcohols
Decarboxylation reactions Beta-Ketoacids yields elimination of -COOH plus CO2;Beta-Dicarboxylic acids yields carboxylic acid and CO2
soap hydrophobic and hydrophillic
Oxidation at a Benzylic Position a benzylic carbon bonded to at least one hydrogen is oxidized to a carboxyl group
Oxidition of benzene yields aromatic dicarboxylic acid using K2Cr2O7 and H2SO4
Chlorination/Bromination of Benzene the electrophile is a halonium ion, Cl+ or Br+, formed by treating Cl2 or Br2 with AlCl3 or FeCl3
Chlorination/Bromination of Benzene yields Halobenzene plus HX using AlCl3 or FeCl3
Nitration of HaloBenzene the electrophile is the nitronium ion, NO2+, formed by treaing nitric acid with sulfuric acid
Nitration of HaloBenzene yields -NO2 at ortho and para positions plus H2O
Sulfonation of Benzene the electrophile is HSO3+
Sulfonation of Benzene yields Ar-SO3H plus H2O using H2SO4
Friedel-Crafts Alkylation of Benzene the electrophile is an alkyl carbocation formed by treating an alkyl halide with a Lewis Aci
Friedel-Crafts Alkylation of Benzene R-Cl yields Ar-R plus HCl using AlCl3
Freidel-Crafts Acylation The electrophile is an acyl cation formed by treating an anyl halide with a Lewis acid
Freidel-Crafts Acylation Benzene plus chlorinated aldehyde (CH3C=OCl)with AlCl3
Benzene plus chlorinated aldehyde (CH3C=OCl)with AlCl3 yields ArC=OCH3 plus HCl
Alkylation using an alkene on benzene the electrophile is a carbocation formed by treating an alkene with H2SO4 or H3PO4
para-Methyl-phenol plus 2 (CH3)2C=CH2 with H3PO4 yields diortho isopropyl(C(CH3)3) para-methyl phenol
Alkylation using an alcohol on benzene the electrophile is a carbocatio formed by treating an alcohol with H2SO4 or H3PO4
benzene plus isopropylalcohol with H2SO4 yields isopropyl benzene plus water
acidity of phenols phenols are weak acids
phenol plus water yields phenoxide ion ArO- plus H3O+ pka=9.95
phenol plus water substitution by electron-withdrawing groups, such as teh halogens and the nitro group, increases the acidity of phenols
phenols with strong bases water-insoluble phenols react quantitatively with stron bases to form water-soluble salts
phenols with strong bases(NaOH) yield Sodium phenoxide(ArO-Na+) and water
formaldehyde with grignard reagent(C6H5MgBr) followed by hydrolysis(H2O) in aqueous acid(HCl)yields primary alcohol C6H5C(OH)HCH3
treatment of any aldehyde besides formaldehyde with Grignard reagent, hydrolysis, and aqueous acid yields secondary alcohol
Treatment of ketone with a grignard reagent yields tertiary alcohol
Ketone(CH3(C=O)CH3) plus grignard reagent(C6H5MgBr)+ H2O with HCl yields C6H5(COH)(CH3)2 or another way of saying it as (Ar-COH(CH3)2)
Addition of Alcohols to Form Hemiacetals Hemiacetals are only minor components of an equilibrium mixture of aldehyde or ketone and alcohol, except where the -OH and C=O groups are parts of the same molecule and a five- or sic-membered ring can form
Addition of Alcohols to form hemiacetals 4-hydroxypentanal CH3C(OH)HCH2CH2(C=O)H forms equilibrium more towards hemiacetal with methyl group on one end and alcohol on the other and an oxygen conecting the 4 rings of carbon between the methyl and alcohol groups
addition of alcohols to form acetals cyclopentane=O plus HOCH2CH2OH catalyzed by acid H+ equilibrium yield to cyclopentane with two oxygens connecting two CH2 in a cyclical manner plus water
Addition of Ammonia and Amines the addition of ammonnia or a primary amine to the carbonyl group of an aldehyde or a ketone forms a tetrahedral caronyl addition intermediate. Loss of water from this intermediate gives and imine(schiff base)
cyclopentane=O plus H2NCH3 catalyzed with acid(H+) equilibrium yields cyclopentane=NCH3 plus H2O
Reductive Amination to Amines the carbon nitrogen double bond of an imine can be reduced by hydrogen in the presence of a transition metal catalyst to a carbon-nitrogen single bond
cyclohexane=O plus H2N-cyclohexane dehyrates(-H2O) into cyclohexane=N-cyclohexane intermediate
cyclohexane=N-cyclohexane intermediate adding H2/Ni to form cyclohexane-NH-cyclohexane
Keto-Enol tautomerism the keto form generally predominates at equilibrium
Oxidation of aldehyde to a carboxylic acid the aldehyde group is among the most easily oxidized functional groups. Oxidizing agens include H2CrO4, tollens' reagent, and O2
Benzene ring with -C(=O)H and adjacent -OH group plus Ag2O with THF,H2O, NaOH then H2O, HCl yields benzene ring with carboxylic acid and adjacent alcohol plus Ag
Catalytic Reduction of a carbonyl group in an aldehyde or ketone to a hydroxyl group is simple to carry out and yields of alcohols are high
cyclohexane=O plus H2 with Pt at 25 degrees celsius and 2 atm yields cyclohexane-OH
Metal hydride reduction or carbonyl group both LiAlH4 and NaBH4 reduce the carbonyl group of an aldehyde or a ketone to an hydroxyl group. They are selective in that neither reduces isolated C=C only C=O
cyclohexene=O with NaBH4 and H2O yields cyclohexene-OH C=C in not reduced on C=O
acidity of Carboxylic acids values of pka for most unsubstituted aliphatic and aromatic carboxylic acis are within the range from 4 to 5.
Substitution by electron-withdrawing groups to carboxylic acids acidity is increased pka decreases
Reaction of Carboxylic Acids with Bases forms water-soluble salts with alkali metal hydroxides, carbonates, bicarbonates, ammonia, and amine bases
Ar-COOH + NaOH with H2O yields Ar-COO-Na+ plus H2O
Reduction of Carboxylic Acid with LiAlH4 and H2O reduces carboxyl group to a primary alcohol basically hydrogenating the carbonyl group
cyclopentene-COOH plus LiAlH4 and H2O yields cyclopentene-CH2OH
Reversible Fischer-Esterification Carboxylic Acid + Alcohol and H2SO4 yields ester and H2O
CH3COOH + HOCH2CH2CH3 equilibrium with H2SO4 environment yields CH3COOCH2CH2CH3 + H2O
Making Fischer-Esterification yield ester by adding excess alcohol reagent
Conversion of Carboxylic Acid to Acid Chloride by treating carboxylic acid with thionly chloride SOCl2
CH3CH2CH2COOH plus SOCl2 yields CH3CH2CH2C=OCL + SO2 + HCl
Decarboxylation of Beta-Ketoacids involves redistribution of bonding electrons in a cyclic, six-membered transition state
Cyclohexane(C=O)with adjacent(COOH) warmed yields Cyclohexane(C=O) changing COOH to CO2
Decarboxylation of Beta-Dicarboxylic Acids is similar to Decarboxylation of B-Ketoacids
HOOCCH2COOH plus heat yields CH3COOH plus CO2
common oxidizing agents for ketones to dicarboxylic acids oxidative cleavage via their enol form where C=O gets made into beta-double bonding and C-OH
common oxidizing agents for ketones to cyclo-COOH to aliphatic HOOC-R-COOH potassion dichromate and potassium permanganate at higher temps and high concentration of HNO3 nitric acid
Created by: elainero