Chemistry B11 Chapters 14 Amines, Aldehydes, Ketones And .
Chemistry B11Chapters 14Amines, aldehydes, ketones and carboxylic acidsAmines: are derivatives from ammonia (NH3).Aliphatic amines: an amine in which nitrogen is bonded only to alkyl group or hydrogens.Aromatic amines: an amine in which nitrogen is bonded to one or more aromatic rings.Note: amines are classified as primary ( 1), secondary ( 2) or tertiary ( 3), depending onthe number of carbon groups bonded to nitrogen.CH3 -NH2Methylamin e(a 1 amine)HCH3 -N-CH3D imeth ylamine(a 2 amine)CH3CH3 -N-CH3Trimeth ylamine(a 3 amine)Naming of 1 amines: IUPAC names for aliphatic amines are similar to alcohols except thefinal “-e” of the parent alkane is dropped and replaced by “-amine”. The parent chain whethercontains the nitrogen atom or amino group (NH2).Note: The location of the amino group (-NH2) on the parent chain is indicated by a number(as we do for the 2-CH2-NH21,4-ButandiamineNote: Aniline is the most famous common names for aromatic amines. We begin numberingchain of aromatic by amino group (NH2) (because it is a special substituent). We number thecarbon atoms to obtain the smallest set of numbers and then list them by alphabetical order asa prefix (as we do for the alcohols).NH2NH2NH2NH2ClCH3A nilineNO24-N itroaniline( N itroan ing of 2 and º3 amines: when we have more than one carbon atom bonded to nitrogenatom: the largest group bonded to nitrogen is taken as the parent amine, the smaller groupsbonded to nitrogen are named, and their locations are indicated by prefix N (indicating thatthey are bonded to nitrogen).Chemistry B11Bakersfield College
CH 3NHCH3N-Meth ylan ilin eNCH 3N,N -D imethylcyclopentan amin eHeterocyclic amine: an amine in which the nitrogen is one of the atoms of a ring.NNNPyridin e Pyrimidin e(heterocyclic aroPhysical properties of amines: 1. They have very sharp, penetrating odors (like rotten fish).2. They are polar compounds because of the difference in electronegativity between N and H(3.0 – 2.1 0.9). 3. Both primary and secondary amines can form have hydrogen bonds withone another (because of N-H). However, the tertiary amines do not have a hydrogen bondedto nitrogen and, therefore, do not form hydrogen bond with one another (but hydrogen bondsin amines are weaker than hydrogen bonds in alcohols). 4. They have higher boiling pointsthan hydrocarbons but lower boiling points compare to alcohols (with the same molecularweight). 5. Because of hydrogen bonding, they are more soluble in water than arehydrocarbons of comparable molecular weight.Chemical properties of amines: they are weak bases and they can react with acids.H-O-HH CH 3 -N- H :O- HHMeth ylam m oniu mhy dro xide: :: :HCH 3 -N : HMethy lam in e(a bas e)Note: Aliphatic amines are stronger bases than aromatic amines and heterocyclic amines. Allaliphatic amines are slightly stronger bases than ammonia. While aliphatic amines are weakbases by comparison with inorganic bases such as NaOH, they are strong bases amongorganic compounds.Note: Some amines are present in our blood and make it approximately basic (pH 7.4).Aldehyde: the functional group of an aldehyde is a carbonyl group (C O) bonded to ahydrogen atom.OH-C-HOMethanalCH3-C-HEthanalKetone: the functional group of a ketone is a carbonyl group (C O) bonded to two carbonatoms.OCH3-C-CH3Chemistry B11PronanoneBakersfield College
Naming of aldehydes: IUPAC names for aldehydes are similar to alcohols except the final “e” of the parent alkane is dropped and replaced by “-al”. The parent chain should contain thecarbonyl group (C O). We number the carbon chain starting from the end nearest thecarbonyl group and there is no need to use a number to locate the aldehyde group (because thecarbonyl group of an aldehyde can appear only at the end of a parent chain).Common name of aldehydes: for two first aldehydes use the prefix “form-” and “acet-”followed by “-aldehyde”.OHCHOCH3 CHO5634Meth analEthanal(Formaldehyde) (Acetaldeh yd e)O312HHexanal421H3-Methylbutan alNaming of ketones: IUPAC names for ketones are similar to alcohols except the final “-e” ofthe parent alkane is dropped and replaced by “-one”. The parent chain should contain thecarbonyl group (C O). We start numbering the carbon chain from the end nearest thecarbonyl group. For ketones, we need to show the location of the carbonyl group.Note: In naming aldehydes or ketones that also contain the carbon-carbon double bond(C C), we still start numbering the carbon chain from the end nearest the carbonyl group(however, we have an alkene instead of an alkane). We show the location of the carboncarbon double bond by number of its first carbon.O321H2-Prop enalNote: In naming aldehydes or ketones that also contain an -OH or -NH2 group elsewhere inthe molecule, we still start numbering the carbon chain from the end nearest the carbonylgroup. Hydroxy and amino substituents are numbered and alphabetized along with any othersubstituents that might be present.OOH O5436H13-Hydroxy-4-meth ylp entanal4321NH23-Amino-4-ethyl-2-h exanoneCommon name of ketones: name each alkyl or aryl group bonded to the carbonyl group as aseparate word, followed by the word “-ketone”. The alkyl or aryl groups are generally listedin alphabetical order. The first ketone is called acetone.OO1AcetoneChemistry B1123456O2-Butanone(Ethyl methyl ketone)5-Meth yl-3-h exanoneBakersfield College
Physical properties of aldehydes and ketones: 1. Most aldehydes and ketones have strongodors (the odors of ketones are generally pleasant, and many are used in perfumes). 2. Theyare polar molecules (because of carbonyl group (C O), carbon obtains the partial positivecharge and oxygen obtains the partial negative charge). 3. There is only the dipole-dipoleinteraction between the molecules and there is no possibility for hydrogen bonding. 4. Theyhave lower boiling points than amines and alcohols. 5. They are soluble in water (formhydrogen bonds with water - the oxygen atom of each carbonyl group is a hydrogen bondacceptor) and they are not soluble in nonpolar compounds (because they are polar).Chemical reactions of aldehydes and ketones:1. Oxidation: Aldehydes are oxidized to carboxylic acids by a variety of oxidizing agents,including potassium dichromate (K2Cr2O7). In this reaction, a concentrated strong acid is usedas a catalyst (H2SO4). Liquid aldehydes are so sensitive and the oxygen in air can oxidizethem. They must be protected from contact with air during storage. Ketones resist oxidationby most oxidizing agents (no oxidation for ketones).OOHHexanalOC2HK2 Cr 2 O 7H 2 SO 4OHHexanoic acidOC O22BenzaldehydeOHBenzoic acid2. Reduction: we know that the C C double bond of an alkane can reduced by hydrogen inthe presence of a transition metal catalyst (such as platinum) to a C-C single bond. The sameis true of the C O double bond of an aldehyde or ketone to the C-O. Aldehydes are reduced toprimary alcohols and ketones are reduced to secondary alcohols.OPen tanalH H2OCH3 C CH2 CH3 H 22-butanonetran sitionmetal catalysttran siti onmetal catalystOH1-Pen tanolOHCH3 CH CH2 CH32-butanolMechanism of reduction: the reagent most commonly used in the laboratory for thereduction of an aldehyde or ketone is sodium borohydride (NaBH4). This compound is asource of hydride ions (H-). In this ion, hydrogen has two valence electrons (unstable).Hydride ion is attracted to and then adds to the partially positive carbonyl carbon, whichleaves a negative charge on the carbonyl oxygen. Reaction of this intermediate with aqueousacid gives the alcohol.Chemistry B11Bakersfield College
-H:C O HC OH3 O -HC O-HHydrideNote: An advantage of using NaBH4 over the H2/metal reduction is that NaBH4 does notreduce carbon-carbon double bonds (there is no polarity –no partial positive or negativecharges- on a carbon-carbon double bond to attract the negatively charged hydride ion).Carboxylic acid: the functional group of a carboxylic acid is a carboxyl group (-COOH),which is a carbonyl group (C O) attached to a hydroxyl group (-OH). Carboxylic group canbe represented by three ways: -COOH, -CO2H, or the following method:OCH3-C-OHorCH3COOHNaming of carboxylic acids: IUPAC names for carboxylic acids are similar to alcoholsexcept the final “-e” of the parent alkane is dropped and replaced by “-oic acid”. The parentchain should contain the carboxyl group (-COOH). Number the chain beginning with thecarbon of the carboxyl group. Because the carboxyl carbon is understood to be carbon 1, thereis no need to give it a number. We consider the hodroxyl group (-OH) and the amino group (NH2) as a substituent (list them in alphabetical order).O6O13OHHexanoic acidOH1O5OH3-Methylbu tanoic acid1OH5-Hydroxyhexan oic acidNaming of dicarboxylic acids: we add the suffix “-dioic acid” to the name of the parentalkane that contains both carboxyl groups; thus, “-ane” becomes “-anedioic acid”. Thenumbers of the carboxyl carbons are not indicated because they can be only at the ends of theparent chain.OHO4OO51OHO1HOHOOH16OHOOButaned ioic acidPen tanedioic acidHexan edioic acid(Succinic acid)Physical properties of carboxylic acids: 1. They are so polar because they contain threepolar covalent bonds (C O, C-O, and O-H). 2. They have higher boiling points than othertypes of organic compounds of comparable molecular weight (because their polarity and thepresence of the hydrogen bonding between two carboxyl groups (it creates a dimer)).hydrogen bondin gbetw een tw omoleculesH3 CδOOCCOChemistry B11δ HHδ CH 3Oδ-Bakersfield College
3. They are more soluble in water than other types of organic compounds (because ofhydrogen bonding). 4. The liquid carboxylic acids have sharp, often disagreeable odors. 5.They have sour taste (exist in pickles, limes and lemons).Fatty acids: long, unbranched chain carboxylic acids are found in animal fats, vegetable oils,or phospholipids of biological membranes. Nearly all fatty acids have an even number ofcarbon atoms, most between 12 and 20, in an unbranched chain.COOH Stearic acid (18:0)Note: In most unsaturated fatty acids (with double bond C C), the cis isomer is usually existsand the trans isomer is rare.COOHCisNote: the saturated fatty acids are solid at room temperature and they have higher meltingpoints than the unsaturated fatty acids (they are liquid at room temperature). The reason is: thesaturated fatty acids are linear and they can be packed together in close parallel alignment.The attractive interactions between adjacent hydrocarbon chains (London dispersion forces)are maximized. In unsaturated fatty acids, the cis double bonds interrupt the regular packingof the chains and the London dispersion forces is smaller.COOHCOOHCOOHCOOHCOOHEsters: in esters the hydrogen atom in the carboxyl group is replaced with an alkyl group.OEster groupCH3-C-O-CH3Saponification: Natural soap are sodium or potassium salts of fatty acids. They are preparedfrom a blend of tallow and coconut oils (triglyceride). Triglycerides are triesters of glycerol.The solid fats are melted with steam, and the water insoluble triglyceride layer that forms onthe top is removed. the preparation of soaps begins by boiling these triglycerides with sodiumhydroxide (NaOH). Boiling with potassium hydroxide (KOH), gives a potassium soap.OCHOCRO2saponification 3 N aOHRCOCHOCH2 OCRA triglyceride( a triester of glycerol)Chemistry B11CH2 OHCHOH O 3 RCO N aCH2 OH1,2,3-Propanetriol Sodium soaps(Glycerol; glycerin)Bakersfield College
How soap cleans: soap consists of two parts: 1. Hydrophobic part, which is nonpolar and it ismade of fatty acid (long hydrocarbon chain). 2. Hydrophilic part, which is polar and it is madeof carboxylate group (-COO-) with a negative charge and a metal ion (Na or K ). In water,nonpolar hydrocarbon chains tend to cluster in such a way as to minimize contact of theirhydrocarbon chains with surrounding water molecules. The polar part stays in contact withthe surrounding water molecules. Soap molecules cluster into micelles (a sphericalarrangement of molecules). Many of the things we commonly think of as dirt, are nonpolarand insoluble in water. When the dirt and soap are mixed together, the nonpolar hydrocarboninner parts of the soap can dissolve the dirt and they keep the dirt inside of the micelles. Inthis way, the dirt is washed away in the polar wash water.Chemical reaction of carboxylic acids:1. They are weak acids (pKa 4-5). Substituents of high electronegativity (especially -OH, Cl, and -NH3 ), near the carboxyl group increase the acidity of carboxylic acids.2. As they are weak acids, they react with strong bases like NaOH, KOH, and NH3 to formwater-soluble salts.COOH NaOHH2 OBen zoic acidCOOH NH 3 COO Na H2 OSodiu m b enzoateH2 OBenzoic acid(s ligh tly solub le in w ater)-COO NH 4 Ammoniu m b enzoate(20 g/100 mL water)3. Fischer esterification: reaction of a carboxylic acid with an alcohol in presence of an acidcatalyst (most commonly, concentrated sulfuric acid) gives an ester.OCH 3 C-OH Eth anoic acidChemistry B11H-OCH2 CH3Eth anolH2 SO4OCH3 COCH 2 CH3 H2 OEthyl ethanoateBakersfield College
Chemistry B11 Bakersfield College Chemistry B11 Chapters 14 Amines, aldehydes, ketones and carboxylic acids Amines: are derivatives from ammonia (NH3). Aliphatic amines: an amine in which nitrogen is bonded only to alkyl group or hydrogens. Aromatic amines: an amine in which nitrogen is bonded to one or more aromatic rings. Note: amines are classified as primary ( 1), secondary .
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Naming aromatic amines 17.4 Isomerism for Amines Constitutional isomerism in amines can arise from several causes. Different carbon atom arrangements produce isomers and Different positioning of the nitrogen atom on a carbon chain is another cause for isomerism. In secondary and tertiary amines, different partitioning of carbon atoms among the
We have already seen the reaction of various amines with ketones and aldehydes to generate imines and their analogues. E.g. Ch19 Amines(landscape).docx Page 21 Aromatic Substitution of Aryl and Heterocyclic Amines Aryl amines are activating, ortho/para directors in electrophilic aromatic substitution reactions, since the lone pair
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nucleic acids, alkaloid drugs, etc. (Alkaloids are N-containing, weakly basic organic compounds; thousands of these substances are known.) Amines are organic derivatives of ammonia, NH3, in which one or more of the three H’s is replaced by a carbon group. Amines are classified as primary (1 ), secondary
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