INTRODUCTION TO ORGANIC CHEMISTRY. Section A
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1 Section A Q1 The formula CH3 can represent an anion, a cation or a free radical. Species with the molecular formula CH3 can act as an electrophile, a free radical or a nucleophile depending on the number of outer shell electrons on the central carbon atom. How many outer shell electrons must be present for CH3 to act in these different ways? Q2 Pentanol, C5H11OH, has four structural isomers that are primary alcohols. How many of these primary alcohols contain a chiral carbon atom? A 0 B 1 C 2 D 3 Q3 The diagram shows the structure of the naturally-occurring molecule cholesterol. Student X claimed that the seventeen carbon atoms in the four rings all lie in the same plane. Student Y claimed that this molecule displays cis-trans isomerism at the C=C double bond. Which of the students are correct? A both X and Y B neither X nor Y C X only D Y only Q4 Which compound does not show cis-trans isomerism? A 2-methylpent-2-ene B 3-methylpent-2-ene C 3,4-dimethylhex-3-ene D pent-2-ene Q5 Which formulae show propanone and propanal as different compounds? A empirical, molecular, structural and displayed formulae B molecular, structural and displayed formulae only C structural and displayed formulae only D displayed formulae only Q6 How many isomers with the formula C5H10 have structures that involve π bonding? A 3 B 4 C 5 D 6 Q7 How many isomeric esters have the molecular formula C4H8O2? A 2 B 3 C 4 D 5 ZAHID IQBAL WARRAICH
2 Q8 Which diagram gives the skeletal formula of 2-chloropentan-3-ol? Q9 Isomers X and Y both react with HBr. A mixture of X and Y is reacted with HBr. Which three structures represent three different possible products of this reaction? Q10 The following compounds are found in the seaweed Asparagopsis taxiformis. Which compound could show both cis-trans isomerism and optical isomerism? Q11 Pentane, C5H12, is reacted with chlorine in the presence of ultraviolet light. A compound R is found in the products. R has molecular formula C5H10Cl 2. Each molecule of R contains one chiral carbon atom. Which two atoms of the pentane chain could be bonded to chlorine atoms in this isomer? A 1 and 3 B 1 and 5 C 2 and 3 D 2 and 4 Q12 How many isomers, including structural and stereoisomers, with the formula C4H8 have structures that involve π bonding? Q13 In the general formula of which class of compound, is the ratio of hydrogen atoms to carbon atoms the highest? A alcohols B aldehydes C carboxylic acids D halogenoalkanes ZAHID IQBAL WARRAICH
3 Q14 The molecule shown is optically active. How many chiral carbon atoms are present in this molecule? Q15 Carvone is found in spearmint. Q16 An alkene has the formula CH3CH=CR CH2CH3 and does not possess cis-trans isomers. What is R? A H B Cl C CH3 D C2H5 Q17 Menthol is an important compound extracted from the peppermint plant. ZAHID IQBAL WARRAICH
4 How many chiral centres are there in one molecule of menthol? Q18 What is the skeletal formula of 2-methylpentan-1-ol? Section B Q19 What is always involved in a carbon-carbon π bond? 1 a shared pair of electrons 2 a sideways overlap of p orbitals 3 delocalised electrons Q20 What are the same for a pair of optical isomers? 1 their empirical formula 2 their functional groups 3 their structural formula Q21 Disaccharides, C12H22O11, are important in the human diet. For example, sucrose is found in pastries and lactose occurs in milk products. Both of these compounds can be hydrolysed. Which statements about these hydrolysis products are correct? 1 Glucose and fructose have structural isomers. 2 Glucose and galactose are optical isomers. 3 Glucose and galactose are ketones. ZAHID IQBAL WARRAICH
5 MCQ Solution 1. A 2. B 3. B 4. A 5. C 6. D 7. C 8. A 9. B 10. B 11. A 12. D 13. A 14. A 15. D 16. D 17. C 18. C 19. B 20. A 21. B ZAHID IQBAL WARRAICH
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