chem 219 module 6 exam with complete solution

R-NH2 R-NH2 Choose matching term 1 primary amine 2 higher than alkanes lower than alcohols 3 two main steps of reductive amination? 4 cyclohexylamine Don't know? Terms in this set (124) Original amine derivative of ammonia where one or more hydrogen replaced by carbon-based groups primary amine R-NH2 Previous Play Next Rewind 10 seconds Move forward 10 seconds Unmute 0:01 / 0:15 Full screen Brainpower Read More secondary amine R2NH tertiary amine R3N Ammonia NH3 quarternary amine a configuration in which nitrogen has four bonds with other atoms and, as such, the molecule has an electron deficit name by alkyl group +amine at the end naming simple amines Ethylamine diethylamine triethylamine cyclohexylamine name parent chain and then name amine as amino substituent naming amines with additional functional groups present 3-aminobutanoic acid 2,4-diaminobenzoic acid 1,4-diaminobutane 4-amino-2-butanone name amine as N-substituted where largest compound = parent name other groups as N-alkyl substituents naming unsymmetrically substituted 2nd and 3rd degree amines N-ethyl-N-methylpropylamine N,N-dimethylpropylamine N-ethyl-N-methyl-cyclohexylamine amino groups direct attached to aromatic ring aryl amine naming aninline/ aminobenzene benzylamine trigonal pyramidal, 109.5 bond angle amine geometry polar amine polar or nonpolar? primary and secondary amines can form intermolecular hydrogen bonds amine hydrogen bonding? higher than alkanes lower than alcohols boiling points of 1st and 2nd degree amines? N-H bond weaker than O-H bonds bc N is less electronegative than O why are amines lower bp than alcohols? can accept hydrogen bonds but cannot make them intermolecularly can tertiary amines have hydrogen bonds? small amines (up to 6 carbons) are soluble are amines soluble in water? in alcohol? solubility decreases as molecular weight increases amine aqueous solubility does what? basic and nucleophilic are amines acidic or basic? pKb (lower score = more basic) what measures bases alkyl: 3-4, aromatic: 9 (resonance sharing in aromatic) pKb of alkyl amines vs aromatic amines amine ammonia + alkyl halide = 1. ammonia as nucleophile displaces halide ion via Sn2 reaction m hydroxide (base) added to deprotonate the alkylammonium cation to produce the "free base" of the amine 2 steps to alkylation of ammonia and amines alkyl halide added to an ammonia to create an amine alkylation of ammonia and amines secondary amine (R2NH) what does a primary amine alkylate to? tertiary amine (R3N) What does a secondary amine alkylate to? quaternary ammonium salt what does a tertiary amine alkylate to? can produce all degrees of amines what is advantage of alkylation of amines ? Polyalkylation: yield a mix of amine products because no reaction stops cleanly after a single alkylation what is the disadvantage of alkylation of amines? use large concentration of ammonia or amines as the excess helps the halides not react with the new amines created how to combat possible polyalkylation? reduced state all bonds to Nitrogen are either Carbons or Hydrogens Catalytic Hydrogenation reducing an aromatic nitrogen compound to an aromatic primary amine on a metal catalyst like nickel or platimum with the addition of high pressured hydrogen gas surface-catalyzed reaction H2 + nitro compounds are absorbed to the surface of the metal where reduction takes place. The reduction product desorbs from the surface of the metal back into the reaction mixture Lithium Aluminum Hydride (LiAlH4) what molecule can be used to reduce amides to amines? 1st, 2nd, and 3rd degree amines what type of amines can be produced by reducing amides? tin(II) chloride + HCL followed by aqueous sodium hydroxide chemical reducing agent to use rather than highly flammable pressurized hydrogen? primary amines what do nitriles reduce to? 1) LiAlH4 (chemical reagent) 2) H2(g)/Ni (catalytic hydrogenation) what two molecules can be used to reduce a nitrile? Reductive Amination Name the process where amines can be reduced in a single pot by treating aldehyde or ketone with ammonia or an amine (1, or 2) in the presence of a reducing agent two main steps of reductive amination? 1. ammonia adds to C=O bond to produce imine 2. reducing agent converts imine to amine NaBH4 (Sodium borohydride) or catalytic hydrogenation reducing agents for reductive aminiation? avoids polyalkylation why is reductive amination superior to direct alkylation? Nucleophilic Acyl Substitution amines function as nitrogen nucleophiles and the amine is acylated to create an amide 1st and 2nd degree amines which amines can undergo nucleophilic acyl substitution? tertiary amines do not have NH bonds to substitute an R-C=O bond for a hydrogen why cant 3rd degree amines undergo nucleophilic acyl substitution? pyridine or non-nucleophilic bases what is used to neutralize the acid byproduct of nucleophilic acyl substitution? diazotization of primary aromatic amines what unique reaction does aniline undergo with nitrous acid (HONO)? very low temperatures what temps most diazotization be reacted at? generated by combining sodium nitrate (NaNO2) with concentrated HCL at very low temps how is the nitrous acid generated for diazotization? Diazonium Ion N(triple bond)N+ (no NH bonds) only primary amines (have the 2 hydrogen bonds necessary for reaction to occur) which amines can undergo diazotization? leave a nitrogen gas (bubbles out of the mixture) how do diazonium ions leave? nitrile, aryl halides, phenol, etc examples of molecules that replace diazonium ions? carboxylic acids what are amides derivatives of? amides are least reactive derivatives how do amides compare to other carboxylic acid derivatives in reactivity? amide general molecular structure N-C=O 1 carbon based group attached directly to the nitrogen primary amide 2 carbon based groups attached to N secondary amide 3 carbon groups attached to N, no hydrogens tertiary amide replace oic acid or ic acid from the carboxylic acid parent and replace ending with amide how to name amides with unsubstituted NH2 groups Methanamide/ Formamide name this structure ethanamide/ acetamide What is the name of this structure? pentanamide name this structure? carboxamide for cyclic derivatives of amides, what do you replace the carboxylic acid name with? cyclopentanecarboxamide name this molecule benzenecarboxamide (benzamide) name this molecule 1. identify substituent groups attached to the Nitrogen 2. identify parent name 3. list substituents in alpha order preceded by letter N when amide is substituted, how do we name them? N-methylpropanamide name this molecule N, N-dimethylmethanamide name this molecule trigonal planar geometry geometry of amides? resonance contributors of C=N doulbe bond greatly restirct the rotation around the C-N bond why does the amide have its specific geometry? highly polar are amides polar or nonpolar? yes- strong hydrogen bonds to each other and to water and alcohol do amides form hydrogen bonds? Dimers (two hydrogen bonded amides) (similar to carboxylic acid) what state do amides often exist as? High BP (made lower with more alkyl substitution on the nitrogen atoms) generally do amides have high or low boiling points? can act as base by accepting an acidic proton (just like amines) are amides acids or bases? amines are much stronger bases d/t the resonance of amides which delocalizes the lone pair of electrons making it less available for bonding to the acidic protons are amides or amines stronger bases? amides nucleophilic acyl substitution turns ammonia and amines into? 1st, 2nd, and 3rd degree amides what does reacting ammonia or 1st or 2nd degree amines with acid halides, acid anhydrides, or esters? least: amide, ester, acid anhydride, acid halide: most order of carboxylic acid derivatives from least to most reactive? a less reactive acid derivative what can you convert more reactive acid derivatives to? slow reaction time, prolonged heating, harsh conditions with a strong acid or base, water what type of conditions are needed to break down amide bonds? carboxylic acid what is the product of an acid or base catalyzed hydrolysis of an amide? amines what can amides reduce to using lithium aluminum hydride? nitrile / cyano group Nitrile functional group C triple bond N -nitrile as a suffix to the alkane name Carbon of the nitrile group is included with parent chain as position #1 for naming acyclic simple nitriles: See 24 more Add or remove terms Choose a study mode