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• Carbonyl compounds


  Compounds containing a carbonyl group (the -C=O group)

  
• Carbonyl group


  • The most important functional group in organic chemistry
  • Part of most biological molecules
  • Part of most pharmaceutical agents
  • Part of many synthetic chemicals
• Class I carbonyl compounds

  • Acyl group is attached to an atom or a group that can be replaced by another group
  • Includes carboxylic acids, acyl halides, acid anhydrides, esters, amides

  
• Class II carbonyl compounds

  • Acyl group is attached to a group that cannot be readily replaced by another group
  • Includes aldehydes and ketones

  
• Properties of carbonyl compounds

  • Polar in nature
  • Insoluble in water but sometimes dissolve other polar molecules
  • Chemically reactive

  
• Carbonyl reduction

  Carbonyl groups are reduced by hydride reagents like LiAlH4 and NaBH4, baker's yeast, or catalytic hydrogenation
• Carbonyl alkylation


  Carbonyl compounds are alkylated using organometallic compounds like Grignard reagents, organolithium reagents, acetylides

  
• Carbonyl alpha-substitution reaction


  Substitution of the alpha hydrogen by an electrophile

  
• Aldehydes


  Carbonyl group bonded to a hydrogen atom and a carbon atom

  
• Ketones


  Compounds with a carbonyl group bonded to two carbon atoms

  
• Ketone compounds

  • Methadone
  • Haloperidol
  • Fenofibrate
  • Bromfenac
  • Bupropion

  
• Carboxylic acids


  • RCOOH, ArCOOH
  • Compounds containing a carboxyl group (carbonyl and hydroxyl group)
  • Serve as starting materials for carboxylic acid derivatives

  
• Carboxylic acids

  • Cholic acid
  • Acetic acid
• Types of carboxylic acids

  • Saturated dicarboxylic acid
  • Unsaturated dicarboxylic acid
  • Aromatic carboxylic acid

  
• Common names of carboxylic acids

  • Greek letters α,β,γ,δ,etc. used to locate substituents
  • α-position is next to the carboxyl group

  
• Properties of carboxylic acids

  • Planar due to sp2 hybridization
  • Strongly associated due to hydrogen bonding
  • Higher boiling points than corresponding alcohols
  • More soluble in water than other organic compounds of similar molecular weight
  • Solubility decreases as hydrocarbon chain length increases
  • Weak acids that react with bases to form salts

  
• Carboxylic Acid


  • R-COOH interacts with water molecules through H-bonding therefore it is more soluble in water than alcohol, ether, aldehyde and ketone of same MW
  • Solubility of R-COOH in water decreases as MW increases due to the presence of hydrophilic carboxyl group and hydrophobic hydrocarbon chain
  • First four aliphatic R-COOH are infinitely soluble in water because the hydrophobic tail is more than counterbalanced by the hydrophilic head
  • As size of the HC chain increases relative to the size of hydrophilic group, water solubility decreases

  
• Acidity of Carboxylic Acid

  • R-COOH are weak acids, they react with bases such as NaOH and NaHCO3 to give metal carboxylate salts, RCO2-M+
  • R-COOH with more than six carbons are only slightly soluble in water, but the alkali metal salts of carboxylic acids are often highly water soluble

  
• Ester


  • Carboxylic derivative where –H was replaced by another R group
  • Common characteristic are pleasant in odor
  • Upon hydrolysis it yields: R-COOH + R-OH
  • Cyclic form is called Lactone

  
• Esters

  • Isoamyl acetate
  • methyl salicylate

  
• IUPAC Nomenclature for Esters

  Named by first identifying the alkyl group attached to oxygen and then the carboxylic acid, with the –ic acid ending replaced by -ate

  
• IUPAC Nomenclature for Lactones

  Simplest lactone are still named by dropping the suffix –ic acid or -oic acid from the name of the parent carboxylic acid and adding the suffix –olactone. The location of the oxygen atom in the ring is indicated by a number of the IUPAC name of the acid is used by the Greek letter, if the common name of the acid is used

  
• Amide


  • Carboxylic derivative where –OH was replaced by amino group
  • Upon hydrolysis it yields: R-COOH + Amines
  • Cyclic form is called Lactam

  
• IUPAC Nomenclature for Amides

  • Amides with an unsubstituted –NH2 group are named by replacing the –ic acid or –oic acid ending with -amide/–carboxamide
  • If the nitrogen atom is further substituted, the compound is named by first identifying the substituent groups and then the parent amide. The substituent are preceded by the letter N to identify them as being directly attached to nitrogen

  
• Acid Anhydride


  • Formed when two carboxylic acid losses water
  • Upon hydrolysis it yields: two R-COOH

  
• IUPAC Nomenclature for Symmetrical Acid Anhydrides

  Symmetrical anhydrides of unsubstituted monocarboxylic acids and cyclic anhydrides of dicarboxylic acids are named by replacing the word –acid with –anhydride

  
• IUPAC Nomenclature for Unsymmetrical Acid Anhydrides

  Unsymmetrical anhydrides those prepared from two different carboxylic acids are named by listed the two acids alphabetically and then adding anhydride

  
• Acid Halides


  Carboxylic derivative where –OH was replaced by halogen

  
• IUPAC Nomenclature for Acid Halides

  Acid halides are named by identifying first the acyl group and then the halide. The acyl group name is derived from the carboxylic acid name by replacing the –ic acid or –oic acid ending with –oyl or the –carboxylic acid ending with –carbonyl

  
• Thioesters: IUPAC Nomenclature

  Named like the corresponding esters. If the related ester has a common name, the prefix thio- is added to the name of the carboxylate: acetate becomes thioacetate, for instance. If the related ester has a systematic name, the –oate or –carboxylate ending is replaced by –thioate or –carbothioate

  
• Organophosphates: IUPAC Nomenclature

  Acyl phosphates are named by citing the acyl group and adding the word phosphate. If an alkyl group is attached to one of the phosphate oxygens, it is identified after the name of the acyl group. In biological chemistry, acyl adenosyl phosphates are particularly common

  
• Amine


  • Organic derivatives of ammonia
  • Contain a nitrogen atom with a lone pair of electrons, making amines both basic and nucleophilic
• IUPAC Nomenclature for Amines

  • Amines can be either alkyl-substituted (alkylamines) or aryl-substituted (arylamines)
  • Amines are classified as primary, secondary or tertiary, depending on the number of organic substituents attached to nitrogen
  • Compounds containing a nitrogen atom with four attached groups also exist, but the nitrogen atom must carry a formal positive charge. Such compounds are called quaternary ammonium salts
  • Symmetrical secondary and tertiary amines are named by adding the prefix di- or tri- to the alkyl group
  • Unsymmetrically substituted secondary and tertiary amines are referred to as N substituted primary amines. The largest alkyl group takes the parent name, and the other alkyl groups are considered N-substituents on the parent (N because they're attached to nitrogen)
  • Primary amines are named in the IUPAC system in several ways. For simple amines, the suffix –amine is added to the name of the alkyl substituent. Alternatively, the suffix –amine can be used in place of the final –e in the name of the parent compound
  • Amines with more than one functional group are named by considering the –NH2 as an amino substituent on the parent molecule

  
• Heterocyclic Amines


  Compound in which the nitrogen atom occurs as part of a ring – are also common, and each different heterocyclic ring system has its own parent name. The heterocyclic nitrogen atom is always numbered as position 1

  
• Nitriles


  • Compounds containing the cyano (-C N) functional group
  • Can undergo some chemistry similar to that of RCOOH
  • Simple open chain nitriles are named by adding –nitrile as a suffix to the alkane name, with the nitrile carbon numbered C1
  • Nitriles can also be named as derivatives of carboxylic acids by replacing the –ic acid or –ioc acid ending with –onitrile or by replacing the carboxylic acid ending with –carbonitrile. The nitrile carbon atom is attached to C1 but is not itself numbered