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Class
CONCEPTS OF ORGANIC CHEMISTRY
XII

1.The IUPAC name of an organic compound consists of (I) word root: -represents number of carbon atom in the parent chain (II) Primary suffix: - represents saturation or unsaturation in the chain (III) Secondary Suffix: - represents functional group (IV) Prefix: - represents the name of alkyl groups (Branches Chain) or same functional group regarded as substituent.

While writing the name: -

Prefix (es) + word root + primary suffix + secondary Suffix

                    CH3- CH1 -CH2 -COOH
                              |
                            CH3                                                                         ® Methyl + but + an + oie acid.

Rules to be followed while naming an organic compound.
1. Longest continuous chain of carbon atom in the parent chain is selected. Carbon of functional group must be included.
2. Numbering of carbon atoms is done in a way that the substituted carbon atoms have the lowest possible number or the carbon with functional group gets the lowest number.
3. If the compound has more than one similar alkyl groups or functional group their position are indicated as di, tri etc.
4. If different alkyl groups are present, their names are written in the alphabetical order.
5. If alkyl group is branched it is named as substituted alkyl group.
6. If different functional are present then the numbering of the parent chain is done in such a way so that functional group of higher priority gets the lower number.

Some examples :-
      6       5      4    3   2     1
A. CH3 - CH2 - CH - C ºC - CH3 - 4 Methyl - 2 - hexyne
                           |
                         CH3
            CH2Cl
               |     1
B. 3CH2 -2CH -CH2 - 1,3 -Dichloro - 2 - (Chloromethyl propane)
      |                |
      Cl               Cl
      4     3     2      1
C. CH2 - C = CH - CH2 OH - 4 chloro - 3 methyl - but - 2 - en - I or
       |        |
      Cl      CH3

7. Alicyclic compounds are derived by putting the prefix `Cyclo' before the word root.
8. In aromatic organic compound a condensed ring is found, which is called nucleus & groups attached to the ring are called side chain. For disubstituted derivatives 1,2 ;1,3;1,4 ortho (0-) Meta (m-) & para (p-) positions are named.
9. Organic reaction process by the attack of certain active species on the reactant molecule. These active molecules are of three types.

(a)Nucleophiles                (b) Electrophiles                    (c) Free radicals
Neutral or -ve charged          Neutral or +vely                   Neutral having unpaired
donate a pair of electron      charged accept a pair           electron cl, Br, OR, R
to substrate molecule           of electron from the
   _   _      _     _                  substrate molecule.
: Cl, :OR,:CN,:NO2
  ..      1 .
H2 O, RoH                         H+,Cl+, Br+ NO+2

10. Organic reaction are of four types: -
A. Substitution reaction: - One atom or group is replaced by the other without changing the rest.
B. Addition reaction: - this reaction are generally give by organic molecules containing multiple bonds. p Bond is broken to 2 sigma bonds.
C. Elimination reaction: - One atom or groups of atoms are removed to form a compound with multiple bonds.
D. Rearrangement reaction: - Involve rearrangement of atoms within the molecules to get different Products.
11. Halealkanes are CnH2n+1X (X is the halogen group)

(a) Preparation from ROH (Alcohol)  + Hx ® Rx + H2O
ZnCl2 - anhydrous C Lucas reagent
+ PCl3® Rx + H3 PO3
+ SOCl2® Rx + SO2­ + HCl­
Thionyl chloride

(b) Industrial preparation from Alkane in presence of chorine light & catalyst
             -HCl           -HCl                 -HCl             -HCl
CH4 + Cl2----> CH3Cl-------> CH2Cl2 -----> CHCl3-------> CCl4
              
            
(c) From alkane
CH2 = CH2 + HI ® CH3 CH2.
For unsymmetrical alkanes it follows Markownikoffs rule is negative part of addendum molecule attaches to carbon having lesser H atom.
In presence of peroxide it gives product against the rule this is called Peroxide or Kharaseu effect.

(D) Holide Exchange
              Acetove
RBr + NaI -------> Rl +NaBr
12. Haloareues are prepared by direct halogeuation in presence of Fecl3, AlCl3

Cl2 + FeCl3 ® FeCl4 + Cl Å

From diazonium salt be the action of ( NaNO2 + HCl)
or (CUCl & CuBr) ® Sandmeyer rkn.

13. Boiling point are in order RCI < RBr < RI. Insoluble in water generally lighter than water.

14. Order of reactivity of Haloalkanes in Iodides > Bromides > Chlorides.


15.

16. Trichlolore thane - Chloroform ,CHCl3, 1,1,1,Trichloro - 2, 2-bis(pculorophenyl ) ethane is D.D.T
17. Alcohol are classified as neonohydric dihydric , trihydric , depending on the number of group present. Monohydric alcohol are classified as Primary (.CH2OH) Secondary (-CHOH) & Tertiary group (³ C+OH) denoted as 1°, 2°, 3° respectively.

18. Preparation of Alcohol
(A) By hydrolysis of Haloalkanes
Rx + KOH(aq) ®ROH + Kx
(B) Hydration of alkanes
                                                        H2O
CH2 = CH2 + H2 So4 ® CH3 CH2 HSO4--------> CH3 CH2 OH
                                                     -HSO4
(C) From aldehyde & ketone
(i) From Grignards regent


(D) BY reduction :-
                     H2/Ni
CH3 CHO + 2H--------> CH3 CH2 OH

Alcohol undergoes 3 types of reaction :-
A. Rkn Involving cleavage of O - H bond
B. Rkn involving cleavage of C - O bond
C.Rkn involving cleavage of alkyl & hydroxyl group.


19.

20. Phenol resembles aliphatic alcohol in many way except
A. it dose not undergo elimination reaction.
B. it dose not undergo reactions involving the cleavage of C - OH bond.
C. if dose not undergo oxidation as alcohol but forms complex product.
Phenol behaves as strong acids than alcohol Phenol reacts with alkyl halides to form. O & p cresol
Periled craft alkylation Phenol can be reduced to benzene be Zinc dust on reaction with ammonia it forms aniline.

                                                     1
21. Ethers :- function Group is R - O - R. It can be simple ethers or symmetrical ethers if both are alkyl group are same & mixed ethers or unsymmetrical ethers when the two-alkyl groups are different.
Ethers are prepared
A. By heating excess of alcohol with conc. H2SO4.
B. By heating alkyl halide with dry silver oxide.
C. By heating alkyl halide with sodium or potassium alkoxides ( Williamson synthesis)


Ethers are colorless, sweet smelling , volatile inflammable substances sparingly soluble in water with very less boiling point as compared than the isomeric alcohol. Chemically ether are less reactive , they do not react with active metals like Na, strong buse like NaoH, reducing or oxidizing agents. In presence of unshared electron pairs on oxygen ethers are basic so they dissolve in strong acids.



22. Aldehyde & ketones have same functional group :
(>c = 0) carbonyl group

H or R                R
        \                \
        C = O          C = O
        /                /
     R                R
Aldehydes show chain & functional isomerism & ketones show chain , functional & metamerism. Primary alcohol forms aldehydes while secondary alcohol's forms ketones. Calcium format with calcium salt of fatty acid other than calcium format yields ketone. Alkynes on hydration gives acetaldehyde. By rosenmud reduction of acid chlorides. By Stephen reduction
( from nitrites) .
Aromatic aldehydes & ketones can be prepared by oxidizing toluene with chromyl chlorine , be treating benzene with CO2 & dry HCI gas , by treating benzene with a mixture of HCN or HCI. Aromatic ketones are prepared by priedel - craft acylation.

23. Acetaldehyde & Acetone with HCN gives Acetaldehyde cyanohydrin, Acetone cyanohydrin. Buzophenone dose not react with HCN.
Formaldehyde reacts with griguard reagent to give primary alcohols, aldehydes other than HCHO gives secondary alcohol & ketones gives tertiary alcohol.

Reaction with hydroxylanine, NH2On forms Aldoximie
RCHO + H2NOH ® R.CH = NOH + H2O
                            Aldoxime.

Reaction with hydrazine , N2N.NH2. forms hydrazone
R.CHO + H2N.NH2 ®RCH = N.NH2
                         Aldenyde hydrazine
CO R + H2N.NH2 ®R2C = N.NH2 + H2O

Halogenation takes more readily than in alkanes.
CH3 CHO + 3Cl2 ® CCl3 . CHO + 3HCl
                             Chloral.

Aldehyde oxides to give acid, Aldehyde & ketone undergo condensation to form aldehyde & diaketone alcohol respectively.
Aldelyde which do not have a Hydrogen where treated with NaoH or koH forms salt of carboxylic acid and alcohol ( cannizzaro reaction)

2HCHO + NaoH ® HCOONa + CH3OH
Formaldehyde. Sod. Format Methyl alcohol

Aldihyde & ketone react rapidly with halogens in presence of alkali to form haloform.

24. Benzaldehyde reacts with ammonia to form hydro benzamide. It reacts with amines to give aromatic anuses. Benzaldehyde when heated with aqueous ethanolic Nacn undergoes self condensation to form benzoin. Benzaldehyde on reaction with PCl5 to form Benzylidene chloride.

25. Carboxylic acid have functional group (-COOH). They exhibit chain , position & functional isomerism. Acid can be prepared by oxidation of alcohol's aldehydes & ketones.
                 K2CR2O7
 CH3CH2OH ------® CH3CHO[O] ®CH3COOH
                                               Acetic acid


Hydrolysis of Cyanides
           acid or                      H2O
CH3.CºN --------> CH3 CONH2 ------> CH3COOH + NH3
           alkali

Hydrolysis of esters with alkali (saponification)
                                KOH
CH3 COO C2 H5 + H2O ------> CH3 COOK + C2H5OH
                                                        Pot. Acetate
From griguards regent & Co2 (dry in) hydrolysis.
o                           o                                   o
ll        CH3Mg I         ll            hydrolysis          ll
C = 0 --------> CH3-C-O Mg I ----------> CH3-C-OH
                                                           Acetic acid.
26. Corboxylic acids are acidic in nature because of stabilization of carboxylate ionic.

27. Carboxylic acids react with metals like Na,K,Zn etc & liberate hydrogen gas. With alcohol it produces esters. On reaction with PCI5 or thorniyl chloride (SOCI2) acid halides are formed.
CH3 COOH + PCl5 ® CH3 COCl + HCl+ POCl3
Acetic acid              Acetyl chloride
Reaction with ammonia gives amide
                                                  heat
RCOOH + 3NH3 ------->RCOONH4 --------> RCONH2.
                                                  -H2O
Dehydration of acid with P2O5 produces anhydride.
Fatty acids react with halogens in presence of a catalyst in sunlight or on boiling to give substituted product. (HVZ run).
                Cl2/P
CH3 COOH --------> CH2Cl COOH          ®Dichlori acetic acid.
                       Honoculoro acetic acid.

Sodium salt of acid with sodium gives alkanes .. ammonium salts on heating form emmides . Dry distillation of calcium salt of acid produces aldelydes & ketones.

28. Carboxyl group is electron withdrawing group. It decreases the electron density at benzene ring & thus, deactivates it towards electrophilic substitution reactions. Substitution mainly takes place at metaposition.


29. Important functional groups containing nitrogen are cyanide -C ºN, Iso cyanide
    ® 
-N = c, Nitro - NO2, Nitrite - O - N = O, Amino - NH2, Imino = NH, Daizo - N+ º N:
Nitrogen compounds can be prepared

(a) treatment of alkyl halides with ken
Rx + KCN -----> RCN + Kx
        alcoholic
               C2H5OH
                                ®
Rx + AgCn -------> RN = C + AgBr
                         isocyanide

Rx + AgNo2----->R-No2 + AgI
                       Nitro Alkane

Rx + 2NH3-----> RNH2 + NH4 X.
                      amine

30. Alkyl cyanides can be prepared by delve duration of primary acids , carboxylates & aldoximes.
     O   H
     ll    l        P2O5
R - C - N - H -------> R - C º N+ H2O
                   heat    Alkyl cyanide
                         P2O5
              +
CH3COO- NH4  --------> CH3 CN +2H2O
                          heat    Ethanenitrite

                     (CH3CO)2O
CH3 CH = NOH ---------> ethunenitrite
                     - H2O

Grignards reagent with CI - Cn give RCN
Isocyanides can be prepared from Amines by Carbylamine reaction
C2H5NH2 + CNCl3 + 3 KOH ------->C2H5NC + 3KCl +3H2O


31. Nitro compounds can be prepared by direct nitration

              
             Conc.H2SO4 
+ HONO2 ----------->  

       NO2
         l

+ H2O
   

Nitrobenzene

 

                                                        

32. Pure primary amnies can be prepared from alkyl halides by Gabriel phthalimide synthesis. On reduction of Alkyl eyanide Amino Alkane is of ammonie on alcohol

                Al2O3,573k              + ROH               +ROH
ROH + NH3------------> RNH2----------> R2NH --------> R3N
                 -H2O                     -H2O                -H2O

-No2 group is reduced either by cetalytic hydrogenation or by chemical means usingFC/HCl or Sn/HC to give amine
             3H2/Ni
R-NO2-------------> R.NH2 + 2H2O

33. Nitride can be hydrolyzed to produce carboxylic acid & ammonium salt.
        H3o+                      HCl
RCN ---------> RCONH2 ---------> RCOOH +NH4+
        HOH                       HOH                 Ammonium salt.

Nitride undergoes reduction to produce primary amines in presence of H2 catalyst.
Pt , Ni, or
Na/C2H5 OH or LiAlH4

                 Pt or Ni
RC º N+H22 ---------> RCH2NH2

Nitrides with griguards reagents gives intermediate salts & on hydrolysis forms ketones.
Esters are produced when alcoholic salt of alkyl cyanide is heated with concentraled H2SO4 or HCl.
                                              O
              l               H+               ll
RC º N+ ROH +H2O ------> R - C - OR1 + NH4+
                                          Ester

34. Isocynides can be hydrolysed in acidic medium to form formic acid & primary amines
        ®                   H+ 
R - N º C + 2HOH -------> RNH2 + HCOOH.

Isocynides can be reduced to give secondary amines . Isocynides react with halogens. Sulphur , mercury oxide etc. to form addition product. On heating Isocynides get converted to alkyl cyanides.

35. Nitro compound is reduced to produced amine reduction takes place by H2/Ni or Zn/HCI or Zn/NH2Cl or LiAlH4, Na3ASO3/NaOH or by electrolysis.

Primary nitroalkanes can be hydrolyzed by boiling with concentrated solution of HCI or 85% H2SO4to form carboxylic acid & hydroxyl amine.
                           HCl
R -CH2- NO2 +H2O------> RCOOH+NH2OH.HCl
                                   Carboxylic Hydroxylamine
                                   acid         Hydro chloride.

Primary & secondary notroalkanes on treatment with Cl2 or Br2 in the presence of NaoH gives halonitro alkanes with Nitrous acid primary, nitroalkane gives Nitrolic acid & secondary gives Pseudonitrole.

36. Like ammonia the primary, secondary & tertiary amines have lone pair of electrons on nitrogen atom so they behave like ammonia i.e. basic character and act as nucleophiles. The basic strength is
2° >1° >3°
Amines react with alkyl halides to form amines of higher class. With acid chlorides amines form substituted amides.Primary aromatic amines with nitrous acid yield aromatic diazonizum salts. Primary aliphatic amines with nitrous acids forms ethanol & ethene. Secondary amines produce nitrosoamines and Tertiary amine forms aromatic amines. Substituted group like Brow, Nitro, sulfro are on ortho & para position.

37. Molecules involved in the bioactivity of a living organism are called Biomolecules eg. Carbohydrate, lipids , proteins, vitamins, hormones, nucleus acids etc.
Carbohydrates are optically active polyhydroxy aldehydes cr. ketones or substances which yield these on hydrolysis. They may be sugars or nonsugars. Sugars can be mono saccharides to Disaccharides & Nonsugar are polysaccharides. Monosaccharides can not be broken to simple sugar & can have two type of carbonyl group :-
aldehydic or ketonic. Disaccharides can be are long chain of monosaccharides.

Glucose (Corn or Blood sugar)     C12H12O6
Suerose (Cane sugar)                C12H22O11
Maltose (Malt sugar)               C12H22O11 
Lactose (Milk sugar)                 C12H22O11
Starch (Amylum)                   (C6H10O5)n
Glucogen                             (C6H10O5)n
Cellulose                             (C6H10O5)n

38.Lipids are organic compounds soluble in nonpolar solvenys like Acetone, Ether, Chloroform, Benzene etc. Lipids are of three types :- simple, compound & derived lipids. Simple Lipids yield fatty acids & alcohol on hydrolysis ( eg. Fats oils.) Compound Lipids yield ( alcohol, fatty acids, phosphoric acid, sugar etc. on hydrolysis & derived Lipids do not have ester linkage they are hydrolysis products of simple & compound Lipids.

39. Amino acids combine to polypeptide chain which in return forms protein. The amino acids are joined by peptide bond between -Co-NH- protein can be simple ( yield only a amino acids on hydrolysis) canjugated (a amino acids & other non - proteinous substances ). Derived protein ( produced by intermediate hydrolysis of protein). Depending on shapes protein can be fibrous ( keratin of hair) or Globular ( haemoglobin).
Proteins are polymers of µ - amino acids linked together by peptides bonds - CoNH2-

1. Primary Structure :- refers to the number, nature & sequence of the amino acids in protein molecule.

2. Secondary structure :-deals with the shape or conformation of the individual polypeptide chain(s) present in the protein molecule

3. Tertiary structure :- refers to its three dimensional structure i.e. , folding & bonding of long peptide chain.

40. Nucleic acids are combination of sugar + nitrogen base + phosphate group.
Sugar can be D-oxyribose sugar (DNA) & ribose sugar (RVA)
Bases can be Purine (Adenine & guanine) or pyramiding ( uracil, thymine & cytosine)
A pairs by a double bond with T
C pairs by a triple bond with G.