IUPAC Organic Chemistry Concepts PDF

# Organic Chemistry ## Berzelius - Organic compound - Those compounds will be formed from waste of living organisms - He proposed vital force theory - These organic compounds cannot be synthesized, artificially in the laboratory, started from inorganic materials ## Wohler - He prepared urea...

# Organic Chemistry ## Berzelius - Organic compound - Those compounds will be formed from waste of living organisms - He proposed vital force theory - These organic compounds cannot be synthesized, artificially in the laboratory, started from inorganic materials ## Wohler - He prepared urea from ammonia cyanate. - (NH4)CNO → H2N-C-NH2 - [Inorganic compound] [organic compound] - Therefore, vital force theory will be collapsed ## Organic Compounds - Hydrocarbon and their derivatives are organic compounds ## Hydrocarbons - Saturated - "C-C" : Alkanes - Eg : CH4 (methane) - CH3 - I - H3C - CI - H3C2 - I - H3C - OH - H3C2 - OH - H3C - COOH - H3C - NH2 - Unsaturated - "C=C" : Alkenes - Eg : C2H4 - H3C - CH - H3C2 - CI - H3C2 - OH - "C≡C" : Alkynes - Eg : C2H2 - H2C - I - HC2 - OH ## Saturated Representation of Organic Compounds 1. Molecular formula (M.F)→ Eg C4H10 2. Condensed structure formula (CSF) → CH3-CH2-CH2-CH3 ## Expanded Structural formula (ESF) - H - H - I - H - H - H - C - H - C - C - C - H - H - H - H ## Bond line Notations (BLN) ## Hybridization - Every molecule attains geometrical shape in which energy is minimum and stability is maximum. - So, Basically hybridization is not a factor which is responsible for the shape of a molecule. - Hybridization - Defined for 1 atom - Not defined for the molecule ## Example | Compound | Hybridization | Shape | |---|---|---| | CH4 | Sp3 | Tetrahedral | | NH3 | Sp3 | Pyramidal | | H2O | Sp3 | V-shape / Bent shape | - Ionic Pair → C= Carbonion → (ve charge is involved) - In hybridization - Hybridization: Sp3 - particle localise (L.P) - participate - Donot - CH2=CH-CH2 - e pair - Sp2 - delocalise - participate in hybridization π Bond ## Structure | Structure | No. σ Bond | No. π Bond | No of bond b/w sp2C - sp3C | |---|---|---|---| | 10 | 5 | 1 | 3 | | 9 | 6 | 0 | 4| ## Degree of Carbon 1. Primary (1°C) : The carbon which is connected to only one other carbon atom. - Example → CH3-CH3 - (1° pri-carbon) 2. Secondary (2°C) : The carbon which is connected to only two other carbon atom. - Example → CH3-CH2-CH3 - 1° - 2° - 1° 3. Tertiary (3°C) : The carbon which cannot to only three other carbon atom. - Example → CH3 - CH - CH3 - 1° - 3°C -1° 5. Quaternary (4°C) : The carbon which is connected to only four other carbon atom. - CH3 - CH3 - C - CH3 - 1° - 4° - 1° - 1° - 1° ## Ques : Calculate the no of : - 1°C = 11 - 2°C = 4 - 3°C = 3 - 4°C = 3 - 1°H = 11×3 = 33 - 2° H = 4×2 = 8 - 3°H = 3×1 = 3 - 4°H = 0 ## Degree of Hydrogen - Degree of hydrogen atom is determined by carbon atom - [1°C - 4H] : Primary hydrogen ## Du of a Compound - Du of a compound is equal to the no. of moles of H2 that must be supplied to convert it into an open chain saturated compound ## Note: - Du = 1 → 1 ring or 1 π-Bond - Du = 2 → 2 rings or 2 × π-Bond or 1 Ring + 1 × π-Bond ## Examples: - Eg :CH2=CH2 - DU = 1 - CH3-CH=CH2 - DU = 1 - CH3 – C = CH - DU = 2 - H3C - CH = CH - C = CH2, - Du = 3 - ☐ → Du = 1 - 6 → Du = 1 ring + 1x π-Bond = 2 - 11 → Du= 2+6 = 8 - 12 → Du= 2 + 2 = 4 - 13 → Du = 8 - 14 → Du = 2 + 2 = 4 - 15 → Cubane - C8H8 → (8 +1) ÷ (8 ÷ 2) = 9 - 4 = 5 ## Degree of Amine - R - NH2 : 1° amine - R - NH - R' : 2° amine - R - N - R' : 3° amine - It is determined by N-atom - It does not depend on the degree of C-atom ### Examples: 1. CH3-CH2-CH2-NH2 → 1° amine 2. CH3-CH-CH3 → 2° amine - NH2 3. CH3 - C - NH2 → 3° amine - CH3 4. CH3-CH2 - NH-CH3 → 2° amine 5. CH3 - N - CH3 → 3° amine - CH3 6. CH3 - N --> 3° amine - H 7. CH3 - N → 3° amine | CH3 8. NH2 → 1° amine 9. NH→ 2° amine 10. NH→ 2° amine 11. OH → 3° amine | N | CH3 ## Degree of Unsaturation / Double Bond - Hydrogen deficient index - CH3–CH - CH3 - CH = CH2 - CH2 = CH2 - CH3 - CH2 - CH3 - If structure is given:- - DU = No of π Bond + No. of ring - If molecule formula is given:- - Du = (C+1) - (H + X - N)÷2 - C → No. of C-atom - X → No. of Halogen - N → No. of N- atom - O and S are neglected. ### Examples: 5. OH → Secondary (2°) 6. <img src="https://i.imgur.com/9y74Dzh.png" alt="A hexagonal structure with a hydroxide substituent"> → Secondary (2°) 7. <img src="https://i.imgur.com/9y74Dzh.png" alt="A hexagonal structure with a hydroxide substituent"> → Tertiary (3°) 8. <img src="https://i.imgur.com/9y74Dzh.png" alt="A hexagonal structure with a hydroxide substituent"> → Secondary (2°) 9. <img src="https://i.imgur.com/9y74Dzh.png" alt="A hexagonal structure with a hydroxide substituent"> → Secondary (2°) 10. <img src="https://i.imgur.com/9y74Dzh.png" alt="A hexagonal structure with a hydroxide substituent"> → Tertiary (3°) ## Degree of Alkyl halide - It is determined by the degree of carbon atom - Example: - CH3-CH3-X → 2°A.H - CH3-CH2-X → 1°A.H - CH3-CH2-CH3 → 1°A.H - CH3 ## Degree of Alcohol - It is determined by the carbon atom - Example: - CH3-CH2-OH → 1° - CH3 - CH - CH2 -OH → 1° - CH3 - CH3 - CH - CH3 → 3° - OH - CH3 - CH - OH →2° - CH-CH3 - CH3 ## Cyclo Octatrienyl Dication - **+** CH=CH CH **+** CH cyclic - It follows huckel's rule - CH=CH - CH - CH=CH - Sp2 carbon: 4n+2=6 - n = 1 - Each C-atom Sp² hybridised - Huckel's rule: 4n+2 = 10 - n=2 ## Delocalized e-pair - 4 × π-Bond - Hybridization ## Homocyclic - These refer to cyclic compounds that contain only carbon atoms - Examples : Benzene, Cyclohexane, Cyclopentane ## Heterocyclic - These refer to cyclic compounds that contain an atom other than carbon - Examples: Pyridine, Pyrrole, Furan ## Alicyclic - Cyclic but not aromatic: - Alicyclic Homocyclic Compound: - ☐ - - - Alicyclic Heterocyclic cyclic: - - ## Aromatic Compounds - Cyclic compound - Condition - Each carbon a - Total no of πe- = 4n +2 - n = 0, 1, 2, 3..... : 14 × πe- - 2 × πe- = 6 × πe- = 10 × πe- ## Note: - An open chain compound can never be aromatic ## Examples: - Benzene - Cyclic ring - Each e- atom sp2 (planer) - Huckel's rule: 4n + 2 = 6 - Aromaticity: 4n = 4, n = 1 ## Aromatic - *Benzenoid* - Benzene - Napthalene - Anthracene - *Non - Benzenoid* - Cyclic - Sp2 (planer) - Cyclopropenyl cation - Huckel's rule: 4n + 2 = 2 - n = 0 - Examples: - 1. <img src="https://i.imgur.com/o4g3t13.png" alt="A pentagonal ring with hydrogen substituents"> - 2. <img src="https://i.imgur.com/eP70Z1c.png" alt="A hexagonal ring with a double bond and hydrogen substituents"> - Sp2 - CH - SP3 - CH - CH - SP3 - CH - Sp2 - CH - Sp2 - H - CH - SP3 - Sp3 - H - Sp3 - Huckel's rule: 4n + 2 = Te- - 4n + 2 = 2 - 4n = 0 ## Homologous series - All members of H.S. ball - Similar chemical property - Different physical property ### Examples: 1. Alkane (CnH2n+2) - CH4 - C2H6 - C3H8 → differ CH2 2. Alkene (CnH2n), - CH2 = CH2 - C2H4 - C3H6 → differ CH2 3. Alkynes: (G.F = CnH2n-2), - C2H2 - C3H4 - C4H6 → differ CH2 4. Alcohol - (C.M.F = CnH2n+1,0) - CH3OH - C2H5OH - C3H7OH - C4H9OH → differ CH2 ## Organic Compound - Acyclic: Acyclic/open chain compound - Straight chain - Branched chain - Cyclic compound - Ring compound - Homocyclic/Carboncyclic (Ring = only c-atom) - Heterocyclic compound (Ring = C + other atom) - Alicyclic compound - Benzene - Napthalene - Anthracene - Aromatic compound - Benzenoid - Non - Benzenoid ## Examples of Naming Cyclic Compounds: - 16. Prismane - C6H6 → (C + 1) - ( H + X – N) ÷ 2 = 7 – 3 = 4 - 17. C6H6→(C+1) -(H+x-N) ÷ 2 = 7-3 = 4 - → 1 ring + 3 × π - bond - 18. C6H6Cl6 → (BHC) - (Benzene hexa chloride or Gammaxane) - <img src="https://i.imgur.com/1pG8z6G.png" alt="Diagram of C6H6Cl6 structure."> - DU= (6 + 1) - (6+6)= 7 – 6 = 1 - 19. C6H4ClNO2 - DU = *(C + 1) - (H + X - N) ÷ 2* = 7 - 2 = 5 - 20. C6H5CIO - DU = *(6 + 1) – (5 + 1) ÷ 2* = 7 - 3 = 4 ## Homologous Series - The series of compound in which members can be represented by general formula ## Characteristics of Homologous Series - Two consecutive members differ CH2 and this molecular mass differ by 14 units. - Functional group it present must be the same for all compounds. - All members of homologous series have the same general methods of preparation. ## Examples: - 5. - C-C-C -C -C -C -C → CH3 - CH - CH - CH2 - CH2 - CH2 - CH3 - 1 CH2 - CH3 - 9-ethyl , 2-methyl heptane (H3 - 6. <img src="https://i.imgur.com/UOCf83b.png" alt="Diagram of a chain with multiple substituents"> - 3, 8 - Diethyle, 2, 4 - Dimethyl 5 - [1- Methyl propyl] 6-[1,2 Dimethyl propyl] Decane. ## Note: - The Di, Tri, Tetra of simple substituent is not considered in alphabetical order whereas Di, Tri, Tetra of complex substituent is considered - Iso, Neo are considered in the alphabetical order whereas secondary and tertiary are not considered ## Ques: 1. CH3-CH-CH-CH3 → 3, 5 dimethyl - Hexane - Et Et - 1 2 3 4 - CH3 – CH – CH – CH3 - CH2 CH2 - CH2 - 6 CH3CH3 - CH - CH2 - CH - CH3 - 1 3 4 2. CH - CH - CH2 - CH2 - CH - CH3 - ipr ipr - CH3 - CH - CH2 - CH2 - CH - CH3 - CH - CH2 - CH3 - CH3 - [2, 3, 6,7 - Tetramethyl octane] ## Note : - [Butyle on Bu] - Common Name | IUPAC |---|--- | N-Butyl | Butyl | Secondary Butyl | 1 methyl propyl | Iso Butyl | 2 methyl propyl | Tertiary Butyl | 1, 1 dimethyl ethyl ## Example: - (i) CH3 - CH - CH2 - CH2 - CH3 → *2methyl pentane* - CH3 - (ii) <img src="https://i.imgur.com/R1P6I60.png" alt="Diagram of a chain with multiple substituents"> - 3ethyl, 2, 2 dimethyl pentane - (iii) CH3 - CH - CH - CH2 - CH3 → (*2, 3 Dimethyl pentane*) - CH3 CH3 - (iv) CH3 - CH - CH - CH2 - CH2 – CH2 - CH3 → *Eth meth* ## Rules: - Longest chain - Numbering where branch is near (Lowest Locant rule). - If parent chain main chain is the same, then more no. of branches more brier. - If methyl or ethyl both are parental is parent chain, we should write all in alphabetical order. ## 1th NEET - **Equilibrium Process and Homogeneous and Heterogeneous Equilibrium** - The vapour density of un-decomposed N2O4 is 46. - It compound has *pri-* prefix: - Open chain: - 1 ring → *cyclo* - 2 ring → *bicycle* - 3 ring → *tricycle* ## Naming of Alkanes - General formula → CnH2n+2. - Example: n = 1: CH4, methane (marsh gas) → found in marshy field - C2H6 → Ethane → CH3-CH3 - C3H8 → Propane →CH3-CH2-CH3 - C4H10 → Butane →CH3-CH2-CH2-CH3 - CH3 - CH - CH3 | CH3 → *2-Methyl propane* ## Side Substituent/Side chain → *Alkyl* - Alkane + ane = tyl - CH4 (Methane) → CH3 - methyl or “me”" - C2H6 (Ethane) → C2H5 - ethyl or “et” - C3H8 → C3H7 -propyl or “pr” - C4H10 → C4H9 - butyl or “bu” ## Note : - CH3 - CH2 - CH3 → <img src="https://i.imgur.com/g3hX05X.png" alt="Drawing of propyl structure with labels"> or <img src="https://i.imgur.com/UOCf83b.png" alt="Drawing of propyl structure with labels"> or <img src="https://i.imgur.com/g3hX05X.png" alt="Drawing of propyl structure with labels"> - <img src="https://i.imgur.com/g3hX05X.png" alt="Drawing of propyl structure with labels"> [Secondary] - <img src="https://i.imgur.com/UOCf83b.png" alt="Drawing of propyl structure with labels"> [Primary] - <img src="https://i.imgur.com/g3hX05X.png" alt="Drawing of propyl structure with labels"> 1-methyl ethane. ## Aromatic Homocyclic Compounds - <img src="https://i.imgur.com/934E7A9.png" alt="Aniline structure"> - Aniline - <img src="https://i.imgur.com/bR8Q14A.png" alt="Phenol structure"> - Phenol - <img src="https://i.imgur.com/6k22G8o.png" alt="Toluene structure"> - Toluene - <img src="https://i.imgur.com/6k22G8o.png" alt="Toluene structure"> - NO2 → Nitrobenzene ## IUPAC: International Union of Pure and Applied Chemistry - Nomenclature of Organic Compounds ## Scheme - Prefix - Root word- Suffix - no. of c-atom - Primary/Secondary Prefix - Functional group - Primary/Secondary suffix - Senior ### Examples: - 1C → meth - -ane ( C-C) - -ene ( C=C) - -yne (C≡C) - 2C→ eth - Saturated - unsaturated - 3C→ prop - 4C → But - 5C → Pent - 6C→ Hex - 7C → Hept - 8C → Oct - 9C → Non - 10C → Dec - 11C → Undec - 12C → Dodec ## If Compound Has - All c-c → *ane* - One c=c → *ene* - Two c=c → *diene* - Three c=c → *triene* - One c≡c → *yne* - Two c≡c → *diyne* - One c=c + 1c≡c→ *enyne* ### Examples: - Eg: - 4 3 2 1 - C = C - C - C = C - 1 2 3 4 5 - 3-ethyl penta-1, 4 diene - Eg: - 3 4 - CH2 - CH - CH3 - CH - CH2 - HC = C – C = C – C = CH2 - CH - CH2 - 1 2 3 4 5 6 - [3, 4 diethyle hexa 1, 3, 5-ene] ## Note: - Side chain/Substitution - -H → Alkene - -e → Alkenyl - Example : - CH2 = CH2 → CH2 = CH – ethenyl, ethenyl - H2C = CH → CH3CH = CH – CH3 → (propenyl) - CH2 = C - CH3 → (methy ethenyl) ## Ques: - <img src="https://i.imgur.com/235vN9j.png" alt="Diagram of a chain with a bromine substituent and carbon-carbon double bond"> - [2-Bromo But-2-ene] - <img src="https://i.imgur.com/235vN9j.png" alt="Diagram of a chain with a bromine substituent and carbon-carbon double bond"> - [1-Bromo But-2-ene] - <img src="https://i.imgur.com/235vN9j.png" alt="Diagram of a chain with bromine substituent and carbon-carbon double bond"> - [4- Bromo But-1-ene] - <img src="https://i.imgur.com/235vN9j.png" alt="Diagram of a chain with bromine substituent and carbon-carbon double bond"> - [But - 2-yn-1-en-3-yne] - <img src="https://i.imgur.com/235vN9j.png" alt="Diagram of a chain with a carbon-carbon triple bond.""> - [Pent-3-yn-1-yne] - <img src="https://i.imgur.com/h6rO73i.png" alt="Diagram of a complex structure with multiple substituents"> - CH2 - - CH=CH- C – CH = CH2 - CH - CH2 - 2 1 3 4 5 - [3, 3- diethyl pent-1, 4-diene] ## Naming of Alkenes - General formula - CnH2n - 1C → Alkene नही होता है (Does not exist.) - Example - C2H4 → CH2 = CH2 → [*ethene*] - C3H6 → CH2 = CH - CH3 → [*propene*] - C4H8 ### Examples - Eg 1. - CH2=CH-CH2-CH3 → [*butene*] or *but-2-ene* - Eg 2. CH2 = CH - CH3 → [*butene*] = *but-2-ene* - Eg 3. - CH3 - CH - CH - CH3 → 2, 3- Dimethyl pentane - CH2 CH3 - CH2 - CH3 - C = C - CH3 - 1 2 3 4 - 2, 3- Dimethyl pent-2-ene - Eg 4. - CH3 - C = C - Me → CH3 - C = C CH3 → [3, 4- dimethyl Hexane] - Et - CH2 CH2 - CH3 CH3 - Hex-3-ene → CH3 - CH = CH - CH = CH - CH3 - Haxene → CH3 - CH = CH – CH = CH - CH3 - 2 4 - Hax 2,4 - aene ## Alkene (Minimum c = 2 and more) - Examples: - Eg 1 : CH2 = CH2 → C2H4 → [*ethene*] - Eg 2 : C = C → *prop-1-ene* ## Naming of Alkyne - General formula: CnH2n – 2 - Example: - CH≡CH → [*ethyne*] - CH≡C - CH3 → [*propyne* ] - CH≡C - CH2 - CH3 → [*but - 4-yne* ] - C≡C → [*but-2-yne*] - CH≡C - C - CH3 → [*3-chlorobut-1-yne*] - CI - C≡C - C≡C → [*but-1, 3-diyne* ] - C≡C - C -C≡C - C≡C → [*1, 3-ethynyl pent 1, 4-diyne* ] - e - C≡C - C - C≡C - C - C≡C → [4-ethynyl oct- 1, 5-diyne] - C≡C - C - C≡C → [3- ethynyl pent- 1-en-u-yne] - C=C - Gethynyl ## Naming of Cyclo Alkanes - *(Max 3 or more carbon atom forms Cycloalkane)* - 1Cx → <img src="https://i.imgur.com/14qXw5D.png" alt="Diagram of cyclopropane structure."> - [*Cyclopropane*] - 2Cx → <img src="https://i.imgur.com/UOCf83b.png" alt="Diagarm of cyclobutane structure."> - [*cyclobutane* ] - 3Cx → <img src="https://i.imgur.com/14qXw5D.png" alt="Diagram of cyclopentane structure."> - [*cyclopentane*] - 4Cx → <img src="https://i.imgur.com/14qXw5D.png" alt="Diagram of cyclohexane structure."> - [*cyclohexane*] - <img src="https://i.imgur.com/O4O1I6v.png" alt="Diagram of cyclopropane with a methyl substituent."> - [*1-methyl cyclopropane*] ## Priority order of functional group: - Functional group|Secondary Name | Prefix Name |---|---|---| | -COOH or -C(=O)OH| -oic acid or carboxyl acid | 4-carboxy!* | -SO3H | Sulphonic acid | Sulpho | -C(=O)-O-C(=O)- | Dic anhydride or Carboxylic anhydride | -C(=O)-O-(Ester) | -oate or carboxylate | Alkanoyloxy, alkoxy carbonyl | - C(=O)-X and - C(=O)-Halide | oyl halide/ carbonyl halide | Halo- carbonyl | -C(=O)-NH2 | Amide / Carboxamide | Carbomoyl | -CN | Nitrite/Carbonitite | Cyano | -CHO | -al / Carboldehyde| OXO/ formyl | -C=O (ketone)| -one | oxo/ keto | -OH | *ol* | Hydrox | -SH (Thioalcohol) | *thiol* | Mereapto | - NH2 (Amine) | *amine* | Amino ## Naming of Carboxylic Acid - R-COOH - 1st part: Alkanoic acid - 1st Carboxy: carbon of COOH is always included in parent chain. ## Examples: - Eg: - -COOH → 2°nd suffix → oic acid - -CH → carboxylic acid - -OH → carboxylic acid ## Functional Group [F.G]: - The group which is responsible for the properties of the compound is known as functional group: - CH3 - CH3 → CH3 - CH2 - OH - ethan → *ethanol* → *acidic property* - H2O [H+ ions] ## Functional Group 1. -OH → *alcohol*| 2. -SH → *Thioalcohol* 3. -O- → *ether* 4. -S - → *thioether* 5. -SO3H → *sulphonic acid* ## Note: - S=O - OH → *sulphate ester* ## Functional Group 6. -C=O → *carboxylic acid anhydride* - C=O 7. -C=O → *carboxylic acid* - OH 8. -C=O - C=O - C → *acid anhydride* 9. -C=O - X → *acid halide* 10. C=O - H → *aldehyde* 11. C=O - - → *ketone* 12. C=O - → *Ester* 13. -NH2 → *(1° amine)* 14. -NH → *(2° amine)* 15. -N → *(3° amine)* 16. -CN → *(cyanide)* 17. C=N-OH → *(oxime)* 18. -N=N - → *(azo)* 19. -N≡N → *(diazonic)* 20. -NC - → *(isocyanide)* - 21. -NO2 - → *(nitro)* 22. –X (F/Cl, Br,I) - *floro, chloro, bromo, iodo* 23. -NO → *nitroso* 24. = O - N - - O → *nitrito* 25. CH - - - CH → *[1, 2 tri cyclopropyl methane]* - 1 - 2 26. <img src="https://i.imgur.com/8T9w8mG.png" alt="Diagrams of a bicyclic structure"> - CH-CH → *[1,1,2,2-tetracyclohexyl ethane]* ## Naming of Bicyclo compounds - <img src="https://i.imgur.com/c01gCq3.png" alt="Diagram of a bicyclic structure"> - 2-ring - Bridge → *[Dewar Benzene]* - [Bicyclo] (2,2,0) Hexane - <img src="https://i.imgur.com/c01gCq3.png" alt="Diagram of a bicyclic structure"> - → [Bicyclo 2, 2, 1 Heptane] - <img src="https://i.imgur.com/c01gCq3.png" alt="Diagram of a bicyclic structure"> - → [ Bicyclo 2, 2, 2 Octane] - <img src="https://i.imgur.com/c01gCq3.png" alt="Diagram of a bicyclic structure"> - → [Bicyclo [2, 2, 1] Hept - 2 - ane) - <img src="https://i.imgur.com/c01gCq3.png" alt="Diagram of a bicyclic structure"> - → [Bicyclo (2,2,2). Oct – a - 2, 5 - diene] ## Examples of Naming Bicyclic Compounds: - 21. <img src="https