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Chemistry · Class 11 Science

Ch 14Basic Principles of Organic Chemistry — Class 11 Chemistry, concept-first.

Among all the elements of the periodic table, carbon alone is able to form an almost unlimited variety of compounds -- everything from methane, with its single carbon atom, up to deoxyribonucleic acid (DNA), which strings together billions of carbon atoms.

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Key concepts

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Structural Representation of Organic Molecules

Covers the full toolkit of ways an organic molecule can be drawn on paper: the full structural (dash) formula and the electron-dot (Lewis) formula, which show every atom and bond/electron explicitly; the condensed formul…

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In previous exams

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Chapter contents

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14.1

Introduction

Among all the elements of the periodic table, carbon alone is able to form an almost unlimited variety of compounds -- everything from methane, with its single carbon atom, up to deoxyribonucleic acid…

14.2

Structural Representation of organic molecules

Before any of a molecule's chemistry can be discussed, it first has to be represented clearly on paper.

14.2.1

Condensed formula

A condensed formula is a deliberate simplification of the full structural formula: rather than drawing out every single covalent-bond dash, some or all of the bonds are simply hidden, and wherever an…

14.2.2

Bond line formula or zig-zag formula

A bond-line (or zig-zag) formula goes a step further than a condensed formula by dropping the element symbols for carbon and hydrogen entirely, keeping only the bond lines themselves.

14.2.3

Drawing the molecules in three dimensions

Because most real organic molecules are genuinely three-dimensional in shape, chemists use four different conventions to project a 3-D molecule onto flat paper, each suited to a slightly different pur…

14.3

Classification of organic compounds

With so many different organic structures to keep track of, chemists needed a systematic way to relate a molecule's structure to its chemical behaviour -- and that need is exactly what motivates class…

14.3.1

Classification based on carbon skeleton

Classification by carbon skeleton looks purely at how a molecule's own carbon atoms are bonded to one another -- this bonded network is called the carbon skeleton, and it is what fundamentally decides…

14.3.2

Classification based on functional group

Classification by functional group instead looks at which specific, reactive group of atoms a molecule carries -- and that functional group is defined precisely as the part of an organic molecule that…

14.4

Nomenclature of organic compounds

Having established how to draw and how to classify organic molecules, the next essential skill is being able to NAME them -- and to name each one so precisely and unambiguously that any chemist, anywh…

14.4.1

Common/trivial names

As organic chemistry developed historically, a new compound was typically given its own individual, one-off name as soon as it was discovered or isolated, well before any systematic naming scheme exis…

14.4.2

IUPAC Nomenclature

As organic chemistry's known compounds multiplied rapidly, and their structures grew steadily more complex, simply inventing a fresh trivial name for every new compound stopped being workable -- diffe…

14.4.3

IUPAC names of straight chain alkanes

The homologous series of straight-chain alkanes provides the PARENT HYDROCARBON building block for every aliphatic IUPAC name -- so before any branching, functional group, or ring can be named, the st…

14.4.4

IUPAC names of branched saturated hydrocarbons

Any branch or side chain hanging off a saturated parent hydrocarbon is itself an ALKYL group (an alkyl substituent).

14.4.5

IUPAC nomenclature of unsaturated hydrocarbons (Alkenes and Alkynes)

Naming alkenes (carbon-carbon double bonds) and alkynes (carbon-carbon triple bonds) uses every rule already given for alkanes, PLUS several additional rules specific to the multiple bond itself.

14.4.6

IUPAC Names of simple monocyclic hydrocarbons

A saturated MONOCYCLIC hydrocarbon (a single-ring, fully saturated compound) is named simply by attaching the prefix 'cyclo-' to the name of the OPEN-CHAIN alkane with the same number of carbon atoms…

14.4.7

IUPAC nomenclature of compounds containing one or more functional groups

IUPAC names for compounds carrying one or more functional groups build on everything already established for the underlying hydrocarbon skeleton, adding the functional group itself in as a prefix and/…

14.4.8

IUPAC nomenclature of substituted benzene

Naming a substituted benzene ring follows its own set of conventions, layered by how many substituents are present.

14.5

Isomerism

Isomerism is the phenomenon in which two or more genuinely DIFFERENT compounds nonetheless share exactly the same molecular formula; any two (or more) such compounds are called isomers of one another.…

14.5.1

Structural isomerism

Compounds that share the same molecular formula but have a genuinely different structural formula are called structural isomers of one another, and the overall phenomenon is called structural isomeris…

14.6

Theoretical basis of organic reactions

Every organic reaction, at bottom, comes down to one or more of a molecule's covalent bonds being broken while one or more new covalent bonds are simultaneously formed, usually because a second reacta…

14.6.1

Types of cleavage of covalent bond

A covalent bond -- a shared pair of electrons holding two atoms together -- can be broken (undergo 'cleavage' or 'fission') in one of two distinct ways.

14.6.2

Types of reagent

Organic reagents are classified into two broad types, based purely on whether they DONATE or ACCEPT electrons when they react with a substrate.

14.6.3

Electronic effects in organic reaction

Beyond simply classifying reagents, organic chemistry also needs a way to explain WHY particular parts of a substrate molecule end up being electron-rich or electron-deficient in the first place, sinc…

14.6.4

Inductive effect

A covalent bond formed between two atoms of genuinely DIFFERING electronegativity is, by definition, a polar covalent bond -- the C-Cl bond is the chapter's running example, since chlorine is consider…

14.6.5

Resonance structures

Resonance theory applies whenever a molecule's Lewis structure contains a CONJUGATED system of pi bonds -- that is, two or more multiple bonds alternating with single bonds along a chain or ring -- or…

14.6.6

Resonance Effect

The existence of resonance within a conjugated system frequently ends up developing a real, ground-state POLARITY in the overall molecule -- and this specific polarity, arising directly from the inter…

14.6.7

Electromeric effect

The ELECTROMERIC effect is, by contrast with the inductive and resonance effects covered above, a genuinely TEMPORARY electronic effect -- one that is shown ONLY by multiple-bonded groups, and only un…

14.6.8

Hyperconjugation

Hyperconjugation is a further, genuinely PERMANENT electronic effect (unlike the electromeric effect, but like the inductive and resonance effects), and it specifically explains the observed relative…

Exercises

+Show 41 questions41 questions
  1. 14.1A. Write condensed formulae and bond line formulae for the following structures. a. H-C-C-C-C-H, a straight four-carbon chain with all hydro…Free
  2. 14.2B. Write dash formulae for the following bond line formulae. a. A bond-line structure; only the fragment 'O' survives in the extracted sourc…Free
  3. 14.3C. Write bond line formulae and condensed formulae for the following compounds a. 3-methyloctane b. hept-2-ene c. 2,2,4,4-tetramethylpentane…Free
  4. 14.4D. Write the structural formulae for the following names and also write correct IUPAC names for them. a. 5-ethyl-3-methylheptane b. 2,4,5-tr…Preview
  5. 14.5E. Identify more favourable resonance structure from the following. Justify. a. CH3-C(=O)-OH and CH3-C(-OH)=O, one neutral and one bearing a…Preview
  6. 14.6F. Find out all the functional groups present in the following polyfunctional compounds. a. Dopamine, a neurotransmitter that is deficient i…Preview
  7. 14.7G. Find out the most stable species from the following. Justify. a. Methyl free radical (CH3•), isopropyl free radical [(CH3)2CH•], tert-but…Preview
  8. 14.8H. Identify the α-carbons in the following species and give the total number of α-hydrogens in each. a. CH3-CH2-CH(⊕)-CH2-CH3 b. H3C-C(⊕)(CH…Preview
  9. 14.9I. Identify primary, secondary, tertiary and quaternary carbon in the following compounds. a. CH3-C(CH3)(CH3)-CH(CH3)-CH2-CH2-CH3 b. A secon…Preview
  10. 14.102. Match the pairs Column 'A': i. Inductive effect ii. Hyperconjugation iii. Resonance effect Column 'B': a. delocalisation of π electrons b…Preview
  11. 14.113. What is meant by homologous series? Write the first four members of homologous series that begins with A. CH3CHO B. H-C≡C-H Also write do…Preview
  12. 14.124. Write IUPAC names of the following A. A structural-formula diagram; not present in the extracted source text. B. A structure; only the fr…Preview
  13. 14.135. Find out the type of isomerism exhibited by the following pairs. A. CH3-CH2-NH-CH2-CH3 and CH3-NH-CH2-CH2-CH3Preview
  14. 14.14B. CH3-CH(OH)-CH2-CH3 and CH3-CH2-O-CH2-CH3Preview
  15. 14.15C. CH3-CH2-NO2 and its structural isomer CH3-CH=N(-OH)=O (an aci-nitro-type form)Preview
  16. 14.16D. A structure containing a C=O group and a structure containing a C-OH with a C=C, printed in the source only as the fragments 'O' and 'OH'…Preview
  17. 14.176. Draw resonance structures of the following: A. PhenolPreview
  18. 14.18B. BenzaldehydePreview
  19. 14.19C. Buta-1,3-dienePreview
  20. 14.20D. Acetate ionPreview
  21. 14.217. Distinguish: A. Inductive effect and resonance effectPreview
  22. 14.22B. Electrophile and nucleophilePreview
  23. 14.23C. Carbocation and carbanionPreview
  24. 14.24D. Homolysis and heterolysisPreview
  25. 14.258. Write true or false. Correct the false statement. A. Homolytic fission involves unsymmetrical breaking of a covalent bond.Preview
  26. 14.26B. Heterolytic fission results in the formation of free radicals.Preview
  27. 14.27C. Free radicals are negatively charged species.Preview
  28. 14.28D. Aniline is a heterocyclic compound.Preview
  29. 14.299. Phytane is a naturally occurring alkane produced by the alga spirogyra and is a constituent of petroleum. The IUPAC name for phytane is 2…Preview
  30. 14.3010. Observe the following structures and answer the questions given below. (i) CH3-CH2-CH2-CHO (ii) CH3-CH(CH3)-CHO a. What is the relation…Preview
  31. 14.3111. Observe the following and answer the questions given below CH3-CH3 --U.V. light--> CH3• + CH3• a. Name the reactive intermediate produce…Preview
  32. 14.3212. An electronic displacement in a covalent bond is represented by following notation. CH3 -- CH2 -- Cl, with δ⊕ on the CH3 carbon, a large…Preview
  33. 14.3313. Draw all the no-bond resonance structures of isopropyl carbocation.Preview
  34. 14.3414. A covalent bond in tert-butylbromide breaks in a suitable polar solvent to give ions. A. Name the anion produced by this breaking of a c…Preview
  35. 14.3515. Choose correct options A. Which of the following statements are true with respect to electronic displacement in covalent bond? a. Induct…Preview
  36. 14.36B. Hyperconjugation involves overlap of ..... orbitals a. σ - σ b. σ - p c. p - p d. π - πPreview
  37. 14.37C. Which type of isomerism is possible in CH3CHCHCH3? a. Position b. Chain c. Geometrical d. TautomerismPreview
  38. 14.38D. The correct IUPAC name of the compound is ..... a. hept-3-ene b. 2-ethylpent-2-ene c. hex-3-ene d. 3-methylhex-3-ene (The compound's own…Preview
  39. 14.39E. The geometry of a carbocation is ...... a. linear b. planar c. tetrahedral d. octahedralPreview
  40. 14.40F. The homologous series of alcohols has general molecular formula ......... a. CnH2n+1OH b. CnH2n+2OH c. CnH2n-2OH c. CnH2nOH (NOTE: the so…Preview
  41. 14.41G. The delocalization of electrons due to overlap between p-orbital and sigma bond is called a. Inductive effect b. Electronic effect c. Hyp…Preview