H2 CHEMISTRY 9647

TUTORIAL 10: INTRODUCTION TO ORGANIC CHEMISTRY
FORMATIVE ASSESSMENT: Each carbon atom can form 4 covalent bonds. Carbon needs to form equivalent orbitals of same shapes and energies by a process known as hybridisation before bonding can occur.

Classification: Aliphatic molecules contain open (straight or branched) chains of carbon skeletons. Alicyclic molecules consist of closed rings of carbon atoms, which may contain single or multiple bonds. Aromatic molecules contain at least 1 benzene ring (ring of 6 carbon atoms where electrons in p-orbitals are delocalized). Functional Groups & Homologous Series: Functional Group consists of an atom or groups of atoms or bond common to a series or family of compounds and it governs the principal chemical properties of the series. A series of compounds containing the same functional group is called a homologous series. Formulae: Empirical formula – gives the simplest ratio of the atoms of each element present. Molecular formula – gives the actual number of atoms of each element present. Condensed structural formula – shows how the constituent atoms are joined together. Full-structural or Displayed formula – shows both the relative placing of atoms and the number of bonds between them. Nomenclature:

(position — prefix substituent) Parent

Indicates the position of the Indicates the number Longest, continuous Arrange in substituent on the carbon of the same carbon chain alphabetical order chain. substituent. (functional group) Number should be as small as possible.

1

involves the removal of a molecule from a larger molecule. (e) Oxidation / Reduction (III) Types of bond fission: (a) Homolytic fission: when the bond breaks. OH-.g. (II) Types of reactions: (a) Substitution: involves replacing an atom (or a group of atoms) by another atom (or groups of atoms). (b) Addition: (c) Elimination: (d) Hydrolysis: involves two molecules joining to form a single new molecule. The rest of the molecule becomes a cation. involves breaking covalent bonds by reaction with water. which are atoms or groups of atoms with unpaired electrons.Reactions of Organic Compounds: (I) Types of reagent: (a) Nucleophiles are negative ions (e. CN-) and compounds in which an atom has a lone pair of electrons (e. each of the bonded atoms takes one electron. one of the atoms take both of the bonding electrons to form an anion. are formed. NH3).g. They are electrically neutral but highly reactive. NO2+) which attack a region where the electron density is high. Isomerism: Isomers are compounds with the same molecular formula but different arrangement of the atoms in the molecule. (b) Electrophiles are reagents (e.g. Free radicals. different arrangement of atoms Stereoisomerism same molecular formula same structural formula but different spatial arrangement of atom Chain Positional Functional Group Geometric (cis-trans) Optical isomerism 2 . (b) Heterolytic fission: When the bond breaks.e. ISOMERISM Structural same molecular formula different structural formula i.

3-dimethylbutane does not give the smallest overall number assigned to the compound. (a) CH3CH CHCH3 CH3 CH3 (b) CH3CHCH=CH2 CH3 (c) CH3CHCO2H CH3 (d) Br Cl CH3C CCH3 CH3 CH3 (e) CH3 C CH CH3 3 CH=CH2 (f) (CH3)2CHCCl=CH2 (g) CH3C(CH3)2CHClCH3 Q1a 2.2-dimethylbutane CH3 H3C H C Cl CH3 C CH3 2-chloro-3. Q1f Functional group: alkene 2-chloro-3-methylbut-1-ene Cl H H C H H C CH3 C C H H Q1c 2-methylpropanoic acid Functional group: carboxylic acid Functional group: alkene Q1g 3-chloro-2.3-dimethylbut-1-ene H H HH C H H C H CH3 C CH3 C C H H Q1b 3-methylbut-1-ene Numbering starts from the carbon with the double bond.3dimethylbutane 3 .DISCUSSION QUESTIONS: 1 Give the IUPAC name for each of the following structures. Q1d 2-bromo-3-chloro-2.3-dimethylbutane Q1e 3.

4 . Give the IUPAC name of the compound ii. bi) pent-2-ene ii) Carbon is sp2 hyridized (bonded to 3 atoms)  trigonal planar iii) double bond consists of a σ and π bond. Predict the hybridization and geometry of the carbon atom (marked with an asterix *) iii. Indicate whether the bonds involved are σ or π bonds (a) CH3CH2C*Br2CH3 (b) CH3CH2CH=C*HCH3 * H3C (c) * Cl Note: There are two asterixes ai) 2. Assign lowest number to substituents by alphabetical order) ii) Carbon on methyl group is sp3 hybridized (bonded to 4 atoms)  tetrahedral Carbon in benzene ring is sp2 hyridized (bonded to 3 atoms)  trigonal planar iii) Carbon in methyl group only has σ bonds. For each of the following compounds. Carbon in benzene ring has 3 σ bonds and 1 π electron in a delocalized π cloud. 2-dibromobutane ii) carbon is sp3 hybridized (bonded to 4 atoms)  tetrahedral iii) All bonds involved are σ bonds.* Substitutents arranged in alphabetical order 2. c) i) 3-chloromethylbenzene (Note: Numbering of carbon atoms in ring can be clockwise or anticlockwise. 3 Write the structural formula for each of the following compounds. i.

CH2ClCH(OH)CH3 c) 3-chloro-3-ethylpentane H H C H H C HH H Cl C C C H H C HH H H CH2BrCH(CH3)CH2CH3 d) 2-methylbut-2-ene H H C H H H H C H C C C H H C H H H CH3CH2CCl(C2H5)CH2CH3 CH3CHC(CH3)2 4.(a) (c) 1-chloropropan-2-ol 3-chloro-3-ethylpentane (b) (d) 1-bromo-2-methylbutane 2-methylbut-2-ene a) 1-chloropropan-2-ol H Cl H C H O C H H b) 1-bromo-2-methylbutane Br H C H H H C C H H C H H H C H H C HH * To show all bonds and arrangement of atoms in compounds. 5 . (a) What do you understand by the term structural isomerism? (b) Draw and name the full structural formulae for all possible isomers of (i) (ii) (iii) (iv) (v) C3H7Cl C3H6Br2 C4H9Br C3H8O C8H10 (Hint: this structure contains a benzene ring) a) Structural isomerism arises due to different arrangement of atoms in organic compounds (different structural formulae) but they have the same molecular formula.

1dibromopropane 2.3dibromopropane No chain isomers or functional group isomers possible for 3bi and 3bii (iii) C4H9Br CH3CH2CH2CH2Br H H C H H C H H C H H H CH3CHBrCH2CH3 H C H H C Br H C H H C H H Positiona l isomers H C Br 1-bromobutane CH2BrCH(CH3)2 H CH3 H C H C H H H 2-bromobutane CH3CBr(CH3)2 H C H CH3 H C Br C H H Chain isomers H C Br 1-bromo-2-methylpropane (iv) C3H8O CH3CH2CH2OH (alcohol) 2-bromo-2-methylpropane CH3OCH2CH3 (ether) 6 .b) i) C3H7Cl CH3CH2CH2Cl H H C H H C H Cl H CH3CHCl CH3 H C H Cl C H H C H H Positional isomers H C H 1-chloropropane (ii) C3H6Br2 CH3CH2CHBr2 Positional isomers H H C H H C H Br C Br H H 2-chloropropane CH3CBr2CH3 H C H Br H C C H CH2BrCHBrCH3 Br Br H H C H C H C H H CH2BrCH2CH2Br H H C H C Br C H H Br H Br H 1.2dibromopropane 1.2dibromopropane 1.

7 .Functional group isomers H H C H H C H H C H OH H H C H O H C H H C H H Propan-1-ol CH3CH(OH)CH3 H H C H C H Methoxyethane Positional isomers H C H OH H Propan-2-ol (v) C8H10 CH3 H CH3 C H H C H H Chain isomers 1.2-dimethylbenzene CH3 CH3 ethylbenzene Positiona l isomers CH3 CH3 1.4dimethylbenzene 5. (a) What do you understand by the term stereoisomerism? (b) Name the two types of stereoisomerism and explain briefly how they arise.3dimethylbenzene 1.

cis-but-2-ene (iv) trans-but-2-ene 8 .(c) Which of the following structures will have cis-trans isomers? (i) CH2=C(CH3)2 (iii) CH3CH=CHCH3 (v) CH2=CHCH2CH=CH2 (d) Mark the chiral carbons (if any) with an asterisk (*). a) Stereoisomerism arises due to different arrangement of atoms in space in organic compounds with the same molecular and structural formula. c) (i) (ii) (iii) H C H3C C CH3 H3C H H C C H CH3 Does not display cis-trans as 2 similar groups (CH3) are attached to the same carbon atom. (i) (ii) (iii) (ii) (iv) CH3BrC=CCl2 C6H5CH=CHCO2H OH OH CH3 C OH H C NH CH3 2 CO2H H C N OH CH3 H2NCH2CO2H (iv) (CH3)2CHCHBrCH3 (e) (v) (vi) CH3CHBrCHBrCH2CH3 Draw the optical isomers for the organic compounds in parts d (i) and d (iv). Optical isomerism – arises when compounds do not exhibit a plane of symmetry and forms mirror images which are non-superimposable. Does not display cis-trans as 2 similar groups (Cl) are attached to the same carbon atom. b) Geometric isomerism – arises to the restriction of rotation about the C=C double bond & when 2 different substituents are attached to each C across the double bond.

H C H3C C H H C H3C CO2H CH3 C H CO2H CH3 cis-isomer trans-isomer (v) Does not display cis-trans as 2 similar groups (H) are attached to the same carbon atom. H H C H C CH2CH=CH2 d) (i) H3C H C * H NH2 H C CH3 C H3C CO2H NH2 CO2H H2N HO2C Mirror (ii) (iii) OH H C OH H3C C H3C OH HO H C CH3 No chiral carbon OH HO * OH Mirror (iv) 9 .

C3H7 as CH2CH2CH3 and C4H9 as CH2CH2CH2CH3 when representing solutions to students. if any). (a) (c) hex-1-ene 2-methylbut-1-ene (b) (d) hex-2-ene 1-chlorobut-2-ene H C C H (a) No geometric isomers1 (b) C3H7 C H C C4H9 H CH3 H C C CH3 H C3H7 H cis-hex-2-ene trans-hex-2-ene 1 To express C2H5 as CH2CH3. 10 .H H C CH(CH3)2 * (CH3)2CHCHBrCH3 (H3C)2HC C Br CH3 Br Mirror H3C (v) (vi) No chiral carbon 2 chiral carbons CH3CHBrCHBrCH2CH3 * CH3CHBrCHBrCH2CH3 * H H3C C Br CHBrCH2CH3 H3CBrHC H C Br CH2CH3 6. Give the structural formulae for each of the following compounds (including geometrical isomers.

73 1 3 6 Let molecular formula be (C3H6O)n Mr of carboxylic acid = (36.3 27.60 × 10 − 4 1000 Since the acid is a monocarboxylic acid. A monocarboxylic acid P occurs in goat’s milk.0 1.1 10.0n = 116. 27.60 × 10 − 4 58.0)n = 58. Neutralisation of a sample of 0.60 x 10-4 0.6 12. P has the following composition by mass: C.0+16.3%.6%. of moles of NaOH = No.99 ≈ 2 11 .18 10. O. 62.28 n = 1.6 cm 3 of 0.0+6.10 g of P requires 8. (Ans: C3H6O. H.6 × 0.0n 8 . C6H12O2) % by mass Ar No of moles Simplest mole ratio Empirical formula: C3H6O C H O 62.10 = 8.H3C C C H (c) No geometric isomers (d) H3C C H C C2H5 H CH2Cl H C C CH2Cl H H3C H cis-1-chlorobut-2-ene trans-1-chlorobut-2-ene 7.3 1.10 = 8.1%. 10.0 5.10 mol dm-3 sodium hydroxide. NaOH ≡ acid No.0 16. of moles of acid = 8.0n 58. Calculate the empirical and the molecular formulae of P.

only one of the pair of enantiomers is obtained. thus the acid is able to rotate polarised light. Why is this so? a) A carboxylic acid with formula C3H5O2Br has two possible structural formulae as shown below: Br H C H H C H C OH O H H C H Br C H O C OH * 3-bromopropanoic acid 2-bromopropanoic acid However only 2-bromopropanoic acid is optically active (b)* C2H5 OH C H CH3 * Note: Ans to 8(b) should be O─H │ H─C≡C─C─CH3 │ H Lowest molecular mass alcohol (containing only C. whereas a solution of 2-hydroxypropanoic acid synthesised from ethanol did not rotate polarised light.∴ Molecular formula of acid = C6H12O2 ASSIGNMENT QUESTIONS 8. (a) A carboxylic acid of the formula C3H5O2Br is optically active. What is its structure? (b) Give the structure of the lowest-molecular-mass alcohol (containing only C. H and O) that is chiral. H and O) that is chiral. When 2hydroxypropanoic acid is isolated from the natural source. (c) A racemic mixture containing an equal amount of both 2-hydroxypropanoic acid enantiomers is formed when the acid is synthesised from ethanol. 12 . (c) A solution of 2-hydroxypropanoic acid isolated from a natural source rotated polarised light to the right.

9.0g Let molecular formula of hydrocarbon be (CH2)n Mr of hydrocarbon = 14. (a) (b) (c) Calculate its empirical formula.3% by mass of hydrogen) is a gas of density 2.0 1.0 1 C H 85.p.50 = 56.0 7. (a) % by mass Ar No of moles Simplest mole ratio Empirical formula: CH2 (b) Molar gas volume at s.4 × 2.7 14. Draw three possible structural formulae for the compound.3 1 2 Molecular formula of hydrocarbon = C4H8 (c) CH2CH2CH2CH2 CH3CH2CHCH2 H C2H5 C H C H H CH3CHCHCH3 H3C C C H H CH3 H CH2C(CH3)2 CH3 C C CH3 Structural isomers cyclobutane But-1-ene But-2-ene 2-methylpropene ADDITIONAL QUESTIONS (ON ISOMERISM) 1) Nov 2004 P3 Q6 (a) 2) Nov 2002 P2 Q5 (a) 13 . 1 mole of the hydrocarbon has a volume of 22. Calculate its molecular formula.t.14 14.50g dm-3 at s.p = 22400 cm3 At s.t.t.4 dm3 Mass of 1 mole of hydrocarbon = 22.0n 14.p.0n = n=4 56.3 12. A hydrocarbon (containing 14.

3) Nov 2000 P2 Q4 (a) 4) Jun 2000 P1 Q6 (a) 14 .