Talk:Amine

Misc References

I added some references to the biological activity section expanded it a tiny bit. I'm sort of a noob to wikipedia and two of my references look a little funny but I can't figrue out why. If someone could fix them, that would be great. They are the last two references in the biological activity page. Also, I agree a quaternary amine should be added to the top graphic. I'll try to remake the graphic when I have time if no one else can get around to it.RabidRabbit23 (talk) 09:38, 29 January 2011 (UTC) Scratch my comment, a quaternary amine is defined by the IUPAC gold book as a different functional group, called iminium. Does anyone think I should remove the mention to quaternary amines in the biological activity section?RabidRabbit23 (talk) 09:48, 29 January 2011 (UTC)

What you call a "quaternary amine" could be a quaternary ammonium cation or quaternary ammonium compound (or salt), for which there is a separate article. There is an image of the generalized structure available there. H Padleckas (talk) 10:51, 29 January 2011 (UTC)

I moved a couple of your sentences from Amine here to the Quaternary ammonium cation (compound) article along with the references you provided. I fixed the link to osmolytes. The other stuff you added I left here, but with a clarification. There is a separate article on iminium, which means compounds with a C=N⁺ moiety. I did not mention iminium in the biological activity section. H Padleckas (talk) 12:45, 29 January 2011 (UTC)

Thank your very much! You didn't quite capture my meaning about the ion pairs though, I rewrote that a little bit and added another reference. Yes you're right quaternary ammonium is the correct term, my bad.RabidRabbit23 (talk) 21:09, 29 January 2011 (UTC)

Table of Kb values

Somebody, please set the table of Kb values right. I added some content, and then, extra values to support it (and messed up the format).

Skeptical Chymist 15:33, 1 May 2008 (IST)

This page's content is so problematic that it likely should be pulled, and recast, only including information that can be entered with certainty, from reliable, verifiable sources. Web citing web IS NOT enough for a reliable encyclopedia entry. (This said, because I have found enough discrepancies, that I cannot recommend.) Prof D. —Preceding unsigned comment added by 98.226.4.152 (talk) 21:31, 15 September 2008 (UTC)

Quaternary Amines

Should really add quaternary amines here.

Josh Cherry 22:40, 13 Oct 2003 (UTC)

a "quaternary amine" being ...?--Smokefoot 22:49, 19 February 2006 (UTC)

An amine with four bonds to carbon bearing a positive charge.RabidRabbit23 (talk) 09:34, 29 January 2011 (UTC)

Scratch my comment, a quaternary amine is defined by the IUPAC gold book as a different functional group, called quaternary ammonium.RabidRabbit23 (talk) 09:46, 29 January 2011 (UTC)

Sentence problem

This sentence is giving me trouble, mostly b/c I'm not an organic chemist, but if it's confusing to me it's likely to be confusing to others. Anyway I hope someone could clarify and then update it in the article:

"However, if any of the carbons bonded to the nitrogen that is part of a carbonyl group, then the compound is considered an amide rather than an amine."

Does this mean -- if any of the carbons in the 'R' group are, in turn, part of a carbonyl group, then the whole deal is an 'amide' instead of an 'amine'

basically 'that is' is ambiguously referring to one of 'the nitrogen' or 'the carbons'

Thx.

Harold MacKiernan 5 Jan 2006 23:11 PST

I'm pretty sure that any carbonyl group adjacent to an N, NH or NH₂ makes it an amide. Perhaps:

"However, if any of the carbons bonded to the nitrogen are also part of a carbonyl group, then the compound is considered an amide rather than an amine." Anand 21:57, 19 February 2006 (UTC)

Drawing

Nice drawing for the nitrile and amide reductions by LAH, but you might revise the nitriles so that R-C-N are linear in the starting material.--Smokefoot 04:52, 20 February 2006 (UTC)

also the amide forming reaction from acid chloride and an alkyl amine is incorrect as one CH2 was lost.--Smokefoot 00:58, 22 February 2006 (UTC)

Properties as bases

the article says that:
The nitrogen atom features a lone electron pair that can bind H⁺ to form an ammonium ion R₃NH⁺. The wiki page about ammonium ion says that its formula is NH₄⁺.
Could somebody correct this ?
What is the name of R₃NH⁺ ? --Colonna 13:36, 25 April 2007 (UTC)

"Ammonium" can refer either to NH₄⁺ itself or more generally to compounds with four groups attached to a positively charged nitrogen - R₄N⁺. NH₄⁺ is just the case where the four R groups are hydrogens and R₃NH⁺ is the case where only one is. --Ed (Edgar181) 14:03, 25 April 2007 (UTC)

What's the correct pronunciation for "amine"?

206.240.25.247 (talk) 03:04, 17 February 2008 (UTC)

There are two different pronunciations in common use; see [1], which even has audio versions. --Itub (talk) 11:49, 18 February 2008 (UTC)

Classes of amine

Should cyclic nitrogen containing organics such as pyrroles be included as a class of amine? At least one of the molecular structures shown in pyrroles meets the definition given in the lead for an amine. If pyrroles are not amines, then that should be mentioned as it is likely many readers would think they are. Qemist (talk) 00:12, 2 May 2010 (UTC)

diagram labels

What is the dashed line? A hydrogen bond? Could someone label it as such? Or if it's labeled in a standardized fashion, at least inform the reader of the standard? —Preceding unsigned comment added by Blafreniere (talk • contribs) 07:03, 17 September 2010 (UTC)

“The chief commercial use of amines is as intermediates in the synthesis of medicines and fibres” .

Amines constitute an important class of organic compounds derived by replacing one or more hydrogen atoms of ammonia molecule by alkyl/aryl group(s). In nature, they occur among proteins, vitamins, alkaloids and hormones. Synthetic examples include polymers, dyestuffs and drugs. Two biologically active compounds, namely adrenaline and ephedrine, both containing secondary amino group, are used to increase blood pressure. Novocain, a synthetic amino compound, is used as an anaesthetic in dentistry. Benadryl, a well known antihistaminic drug also contains tertiary amino group. Quaternary ammonium salts are used as surfactants. Diazonium salts are intermediates in the preparation of a variety of aromatic compounds including dyes. In this Unit, you will learn about amines and diazonium salts.

I. AMINES Amines can be considered as derivatives of ammonia, obtained by replacement of one, two or all the three hydrogen atoms by alkyl and/or aryl groups. For example:

13.1 Structure of Amines

Like ammonia, nitrogen atom of amines is trivalent and carries an unshared pair of electrons. Nitrogen orbitals in amines are therefore, sp3 hybridised and the geometry of amines is pyramidal. Each of the three sp3 hybridised orbitals of nitrogen overlap with orbitals of hydrogen or carbon depending upon the composition of the amines. The fourth orbital of nitrogen in all amines contains an unshared pair of electrons. Due to the presence of unshared pair of electrons, the angle C–N–E, (where E is C or H) is less than 109.5°; for instance, it is 108° in case of trimethylamine as shown in Fig. 13.1.

13.2 Classification

Amines are classified as primary (1°), secondary (2°) and tertiary (3°) depending upon the number of hydrogen atoms replaced by alkyl or aryl groups in ammonia molecule. If one hydrogen atom of ammonia is replaced by R or Ar , we get RNH2 or ArNH2, a primary amine (1°). If two hydrogen atoms of ammonia or one hydrogen atom of R-NH2 are replaced by another alkyl/aryl(R’) group, what would you get? You get R-NHR’, secondary amine. The second alkyl/aryl group may be same or different. Replacement of another hydrogen atom by alkyl/aryl group leads to the formation of tertiary amine. Amines are said to be ‘simple’ when all the alkyl or aryl groups are the same, and ‘mixed’ when they are different.

13.3 Nomenclature

In common system, an aliphatic amine is named by prefixing alkyl group to amine, i.e., alkylamine as one word (e.g., methylamine). In secondary and tertiary amines, when two or more groups are the same, the prefix di or tri is appended before the name of alkyl group. In IUPAC system, amines are named as alkanamines, derived by replacement of ‘e’ of alkane by the word amine. For example, CH3NH2 is named as methanamine. In case, more than one amino group is present at different positions in the parent chain, their positions are specified by giving numbers to the carbon atoms bearing –NH2 groups and suitable prefix such as di, tri, etc. is attached to the amine. The letter ‘e’ of the suffix of the hydrocarbon part is retained. For example, H2N–CH2–CH2–NH2 is named as ethane-1, 2-diamine. In arylamines, –NH2 group is directly attached to the benzene ring. C6H5NH2 is the simplest example of arylamine. In common system, it is known as aniline. It is also an accepted IUPAC name. While naming arylamines according to IUPAC system, suffix ‘e’ of arene is replaced by ‘amine’. Thus in IUPAC system, C6H5–NH2 is named as benzenamine. Common and IUPAC names of some alkylamines and arylamines are given in Table 13.1.

Intext Questions 13.1 Classify the following amines as primary, secondary or tertiary:

13.2 (i) Write structures of different isomeric amines corresponding to the molecular formula, C4H11N. (ii) Write IUPAC names of all the isomers. (iii) What type of isomerism is exhibited by different pairs of amines?

13.4 Preparation of Amines Amines are prepared by the following methods:

1. Reduction of nitro compounds

Nitro compounds are reduced to amines by passing hydrogen gas in the presence of finely divided nickel, palladium or platinum and also by reduction with metals in acidic medium. Nitroalkanes can also be similarly reduced to the corresponding alkanamines.

Reduction with iron scrap and hydrochloric acid is preferred because FeCl2 formed gets hydrolysed to release hydrochloric acid during the reaction. Thus, only a small amount of hydrochloric acid is required to initiate the reaction.

2. Ammonolysis of alkyl halides

You have read (Unit 10, Class XII) that the carbon – halogen bond in alkyl or benzyl halides can be easily cleaved by a nucleophile. Hence, an alkyl or benzyl halide on reaction with an ethanolic solution of ammonia undergoes nucleophilic substitution reaction in which the halogen atom is replaced by an amino (–NH2) group. This process of cleavage of the C–X bond by ammonia molecule is known as ammonolysis. The reaction is carried out in a sealed tube at 373 K. The primary amine thus obtained behaves as a nucleophile and can further react with alkyl halide to form secondary and tertiary amines, and finally quaternary ammonium salt.

The free amine can be obtained from the ammonium salt by treatment with a strong base:

Ammonolysis has the disadvantage of yielding a mixture of primary, secondary and tertiary amines and also a quaternary ammonium salt. However, primary amine is obtained as a major product by taking large excess of ammonia. The order of reactivity of halides with amines is RI > RBr >RCl.

Example 13.1 Write chemical equations for the following reactions: (i) Reaction of ethanolic NH3 with C2H5Cl. (ii) Ammonolysis of benzyl chloride and reaction of amine so formed with two moles of CH3Cl. Solution

3. Reduction of nitriles Nitriles on reduction with lithium aluminium hydride (LiAlH4) or catalytic hydrogenation produce primary amines. This reaction is used for ascent of amine series, i.e., for preparation of amines containing one carbon atom more than the starting amine.

4. Reduction of amides The amides on reduction with lithium aluminium hydride yield amines.

5. Gabriel phthalimide synthesis Gabriel synthesis is used for the preparation of primary amines. Phthalimide on treatment with ethanolic potassium hydroxide forms potassium salt of phthalimide which on heating with alkyl halide followed by alkaline hydrolysis produces the corresponding primary amine. Aromatic primary amines cannot be prepared by this method because aryl halides do not undergo nucleophilic substitution with the anion formed by phthalimide.

6. Hoffmann bromamide degradation reaction Hoffmann developed a method for preparation of primary amines by treating an amide with bromine in an aqueous or ethanolic solution of sodium hydroxide. In this degradation reaction, migration of an alkyl or aryl group takes place from carbonyl carbon of the amide to the nitrogen atom. The amine so formed contains one carbon less than that present in the amide.

Example 13.2 Write chemical equations for the following conversions: (i) CH3–CH2–Cl into CH3–CH2–CH2–NH2 (ii) C6H5–CH2–Cl into C6H5–CH2–CH2–NH2 Solution

Example 13.3 Write structures and IUPAC names of (i) the amide which gives propanamine by Hoffmann bromamide reaction. (ii) the amine produced by the Hoffmann degradation of benzamide. Solution (i) Propanamine contains three carbons. Hence, the amide molecule must contain four carbon atoms. Structure and IUPAC name of the starting amide with four carbon atoms are given below:

(ii) Benzamide is an aromatic amide containing seven carbon atoms. Hence, the amine formed from benzamide is aromatic primary amine containing six carbon atoms.

Intext Question 13.3 How will you convert (i) Benzene into aniline (ii) Benzene into N, N-dimethylaniline (iii) Cl–(CH2)4–Cl into hexan-1,6-diamine?

13.5 Physical Properties

The lower aliphatic amines are gases with fishy odour. Primary amines with three or more carbon atoms are liquid and still higher ones are solid. Aniline and other arylamines are usually colourless but get coloured on storage due to atmospheric oxidation.

Lower aliphatic amines are soluble in water because they can form hydrogen bonds with water molecules. However, solubility decreases with increase in molar mass of amines due to increase in size of the hydrophobic alkyl part. Higher amines are essentially insoluble in water. Considering the electronegativity of nitrogen of amine and oxygen of alcohol as 3.0 and 3.5 respectively, you can predict the pattern of solubility of amines and alcohols in water. Out of butan-1-ol and butan-1-amine, which will be more soluble in water and why? Amines are soluble in organic solvents like alcohol, ether and benzene. You may remember that alcohols are more polar than amines and form stronger intermolecular hydrogen bonds than amines.

Primary and secondary amines are engaged in intermolecular association due to hydrogen bonding between nitrogen of one and hydrogen of another molecule. This intermolecular association is more in primary amines than in secondary amines as there are two hydrogen atoms available for hydrogen bond formation in it. Tertiary amines do not have intermolecular association due to the absence of hydrogen atom available for hydrogen bond formation. Therefore, the order of boiling points of isomeric amines is as follows: Primary > Secondary > Tertiary Intermolecular hydrogen bonding in primary amines is shown in Fig. 13.2.

Boiling points of amines, alcohols and alkanes of almost the same molar mass are shown in Table 13.2.

Table 13.2: Comparison of Boiling Points of Amines, Alcohols and Alkanes of Similar Molecular Masses SL.NO. COMPOUND MOLAR MASS B.P./K 1. n-C4H9NH2 73 350.8 2. (C2H5)2NH 73 329.3 3. C2H5N(CH3)2 73 310.2 4. C2H5CH(CH3)2 72 300.8 5. n-C4H9OH 74 390.3 13.6 Chemical Reaction

Difference in electronegativity between nitrogen and hydrogen atoms and the presence of unshared pair of electrons over the nitrogen atom makes amines reactive. The number of hydrogen atoms attached to nitrogen atom also decides the course of reaction of amines; that is why primary (–NH2), and tertiary amines differ in many reactions. Moreover, amines behave as nucleophiles due to the presence of unshared electron pair. Some of the reactions of amines are described below: 1. Basic character of amines Amines, being basic in nature, react with acids to form salts.

Amine salts on treatment with a base like NaOH, regenerate the parent amine.

Amine salts are soluble in water but insoluble in organic solvents like ether. This reaction is the basis for the separation of amines from the non basic organic compounds insoluble in water.

The reaction of amines with mineral acids to form ammonium salts shows that these are basic in nature. Amines have an unshared pair of electrons on nitrogen atom due to which they behave as Lewis base. Basic character of amines can be better understood in terms of their Kb and pKb values as explained below:

K = [R - N+H3][OH−] / [R - NH2[H2O]

or K[H2O]= [R - N+H3][OH−] / [R - NH2] pKb = –log Kb

Larger the value of Kb or smaller the value of pKb, stronger is the base. The pKb values of few amines are given in Table 13.3.

Table 13.3: pKb Values of Amines in Aqueous Phase NAME OF AMINE PKB Methanamine 3.38 N-Methylmethanamine 3.27 N,N-Dimethylmethanamine 4.22 Ethanamine 3.29 N-Ethylmethylamine 3.00 N,N-Diethylethanamine 3.25 Benzenamine 9.38 Phenylmethanamine 4.70 N-Methylaniline 9.30 N,N-Dimethylaniline 8.92 pKb value of ammonia is 4.75. Aliphatic amines are stronger bases than ammonia due to +I effect of alkyl groups leading to high electron density on the nitrogen atom. Their pKb values lie in the range of 3 to 4.22. On the other hand, aromatic amines are weaker bases than ammonia due to the electron withdrawing nature of the aryl group.

You may find some discrepancies while trying to interpret the Kb values of amines on the basis of +I or –I effect of the substituents present in amines. Besides inductive effect, there are other effects like solvation effect, steric hinderance, etc., which affect the basic strength of amines. Just ponder over. You may get the answer in the following paragraphs.

Structure-basicity relationship of amines Basicity of amines is related to their structure. Basic character of an amine depends upon the ease of formation of the cation by accepting a proton from the acid. The more stable the cation is relative to the amine, more basic is the amine.

(a) Alkanamines versus ammonia Let us consider the reaction of an alkanamine and ammonia with a proton to compare their basicity.

Due to the electron releasing nature of alkyl group, it (R) pushes electrons towards nitrogen and thus makes the unshared electron pair more available for sharing with the proton of the acid. Moreover, the substituted ammonium ion formed from the amine gets stabilised due to dispersal of the positive charge by the +I effect of the alkyl group. Hence, alkylamines are stronger bases than ammonia. Thus, the basic nature of aliphatic amines should increase with increase in the number of alkyl groups. This trend is followed in the gaseous phase. The order of basicity of amines in the gaseous phase follows the expected order: tertiary amine > secondary amine > primary amine > NH3. The trend is not regular in the aqueous state as evident by their pKb values given in Table 13.3. In the aqueous phase, the substituted ammonium cations get stabilised not only by electron releasing effect of the alkyl group (+I) but also by solvation with water molecules. The greater the size of the ion, lesser will be the solvation and the less stabilised is the ion. The order of stability of ions are as follows:

Decreasing order of extent of H-bonding in water and order of stability of ions by solvation.

Greater is the stability of the substituted ammonium cation, stronger should be the corresponding amine as a base. Thus, the order of basicity of aliphatic amines should be: primary > secondary > tertiary, which is opposite to the inductive effect based order. Secondly, when the alkyl group is small, like –CH3 group, there is no steric hindrance to H-bonding. In case the alkyl group is bigger than CH3 group, there will be steric hinderance to H-bonding. Therefore, the change of nature of the alkyl group, e.g., from –CH3 to –C2H5 results in change of the order of basic strength. Thus, there is a subtle interplay of the inductive effect, solvation effect and steric hinderance of the alkyl group which decides the basic strength of alkyl amines in the aqueous state. The order of basic strength in case of methyl substituted amines and ethyl substituted amines in aqueous solution is as follows: (C2H5)2NH > (C2H5)3N > C2H5NH2 > NH3 (CH3)2NH > CH3NH2 > (CH3)3N > NH3

(b) Arylamines versus ammonia pKb value of aniline is quite high. Why is it so? It is because in aniline or other arylamines, the -NH2 group is attached directly to the benzene ring. It results in the unshared electron pair on nitrogen atom to be in conjugation with the benzene ring and thus making it less available for protonation. If you write different resonating structures of aniline, you will find that aniline is a resonance hybrid of the following five structures.

On the other hand, anilinium ion obtained by accepting a proton can have only two resonating structures (kekule).

We know that greater the number of resonating structures, greater is the stability. Thus you can infer that aniline (five resonating structures) is more stable than anilinium ion. Hence, the proton acceptability or the basic nature of aniline or other aromatic amines would be less than that of ammonia. In case of substituted aniline, it is observed that electron releasing groups like –OCH3, –CH3 increase basic strength whereas electron withdrawing groups like –NO2, –SO3H, –COOH, –X decrease it.

Example 13.4 Arrange the following in decreasing order of their basic strength: C6H5NH2, C2H5NH2, (C2H5)2NH, NH3 Solution The decreasing order of basic strength of the above amines and ammonia follows the following order: (C2H5)2NH > C2H5NH2 > NH3 > C6H5NH2

2. Alkylation Amines undergo alkylation on reaction with alkyl halides (refer Unit 10, Class XII).

3. Acylation Aliphatic and aromatic primary and secondary amines react with acid chlorides, anhydrides and esters by nucleophilic substitution reaction. This reaction is known as acylation. You can consider this reaction as the replacement of hydrogen atom of –NH2 or >N–H group by the acyl group. The products obtained by acylation reaction are known as amides. The reaction is carried out in the presence of a base stronger than the amine, like pyridine, which removes HCl so formed and shifts the equilibrium to the right hand side.

Amines also react with benzoyl chloride (C6H5COCl). This reaction is known as benzoylation. CH3NH2 +C6H5COCl → CH3NHCOC6H5 + HCl Methanamine Benzoyl chloride N − Methylbenzamide What do you think is the product of the reaction of amines with carboxylic acids ? They form salts with amines at room temperature.

4. Carbylamine reaction

Aliphatic and aromatic primary amines on heating with chloroform and ethanolic potassium hydroxide form isocyanides or carbylamines which are foul smelling substances. Secondary and tertiary amines do not show this reaction. This reaction is known as carbylamine reaction or isocyanide test and is used as a test for primary amines.

5. Reaction with nitrous acid

Three classes of amines react differently with nitrous acid which is prepared in situ from a mineral acid and sodium nitrite. (a) Primary aliphatic amines react with nitrous acid to form aliphatic diazonium salts which being unstable, liberate nitrogen gas quantitatively and alcohols. Quantitative evolution of nitrogen is used in estimation of amino acids and proteins.

(b) Aromatic amines react with nitrous acid at low temperatures (273-278 K) to form diazonium salts, a very important class of compounds used for synthesis of a variety of aromatic compounds discussed in Section 13.7.

Secondary and tertiary amines react with nitrous acid in a different manner.

6. Reaction with arylsulphonyl chloride Benzenesulphonyl chloride (C6H5SO2Cl), which is also known as Hinsberg’s reagent, reacts with primary and secondary amines to form sulphonamides.

(a) The reaction of benzenesulphonyl chloride with primary amine yields N-ethylbenzenesulphonyl amide.

The hydrogen attached to nitrogen in sulphonamide is strongly acidic due to the presence of strong electron withdrawing sulphonyl group. Hence, it is soluble in alkali.

(b) In the reaction with secondary amine, N,N-diethyl- benzenesulphonamide is formed.

Since N, N-diethylbenzene sulphonamide does not contain any hydrogen atom attached to nitrogen atom, it is not acidic and hence insoluble in alkali.

(c) Tertiary amines do not react with benzenesulphonyl chloride. This property of amines reacting with benzenesulphonyl chloride in a different manner is used for the distinction of primary, secondary and tertiary amines and also for the separation of a mixture of amines. However, these days benzenesulphonyl chloride is replaced by p-toluenesulphonyl chloride.

7. Electrophilic substitution

You have read earlier that aniline is a resonance hybrid of five structures. Where do you find the maximum electron density in these structures? Ortho- and para-positions to the –NH2 group become centres of high electron density. Thus –NH2 group is ortho and para directing and a powerful activating group.

(a) Bromination: Aniline reacts with bromine water at room temperature to give a white precipitate of 2,4,6-tribromoaniline.

The main problem encountered during electrophilic substitution reactions of aromatic amines is that of their very high reactivity. Substitution tends to occur at ortho- and para-positions. If we have to prepare monosubstituted aniline derivative, how can the activating effect of –NH2 group be controlled ? This can be done by protecting the -NH2 group by acetylation with acetic anhydride, then carrying out the desired substitution followed by hydrolysis of the substituted amide to the substituted amine.

The lone pair of electrons on nitrogen of acetanilide interacts with oxygen atom due to resonance as shown below:

Hence, the lone pair of electrons on nitrogen is less available for donation to benzene ring by resonance. Therefore, activating effect of –NHCOCH3 group is less than that of amino group.

(b) Nitration: Direct nitration of aniline yields tarry oxidation products in addition to the nitro derivatives. Moreover, in the strongly acidic medium, aniline is protonated to form the anilinium ion which is meta directing. That is why besides the ortho and para derivatives, significant amount of meta derivative is also formed. However, by protecting the –NH2 group by acetylation reaction with acetic anhydride, the nitration reaction can be controlled and the p-nitro derivative can be obtained as the major product.

(c) Sulphonation: Aniline reacts with concentrated sulphuric acid to form anilinium hydrogensulphate which on heating with sulphuric acid at 453-473K produces p-aminobenzene sulphonic acid, commonly known as sulphanilic acid, as the major product.

Aniline does not undergo Friedel-Crafts reaction (alkylation and acetylation) due to salt formation with aluminium chloride, the Lewis acid, which is used as a catalyst. Due to this, nitrogen of aniline acquires positive charge and hence acts as a strong deactivating group for further reaction.

Intext Question 3.4 Arrange the following in increasing order of their basic strength: (i) C2H5NH2, C6H5NH2, NH3, C6H5CH2NH2 and (C2H5)2NH (ii) C2H5NH2, (C2H5)2NH, (C2H5)3N, C6H5NH2 (iii) CH3NH2, (CH3)2NH, (CH3)3N, C6H5NH2, C6H5CH2NH2. 13.5 Complete the following acid-base reactions and name the products: (i) CH3CH2CH2NH2 + HCl → (ii) (C2H5)3N + HCl → 13.6 Write reactions of the final alkylation product of aniline with excess of methyl iodide in the presence of sodium carbonate solution. 13.7 Write chemical reaction of aniline with benzoyl chloride and write the name of the product obtained. 13.8 Write structures of different isomers corresponding to the molecular formula, C3H9N. Write IUPAC names of the isomers which will liberate nitrogen gas on treatment with nitrous acid. — Preceding unsigned comment added by 202.131.103.196 (talk) 07:26, 31 January 2013 (UTC)