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21) Arrange the following alkenes according to their increasing stability: A) A < B < C < D B) B < C < A < D C) B < A < C < D D) C < B < A < D E) C < A < B < D 22) Hyperconjugation is best described as: A) an interaction between the orbitals on a substrate and orbitals on a nucleophile B) an interaction between σ bonds and π network C) a resonance structure with separated charges D) an interaction between two π networks E) an electrostatic interaction between an electrophile and a nucleophile 23) What is the major product in the reaction between 2-bromo-3-methylbutane and KOtBu in ethanol? A) B) C) D) E) 24) The rate of E2 reaction between an alkyl halide RX and a base B is given by the following expression (k is a rate constant): A) k[RX} B) k[B] C) k[RX]{B] D) k{RX]2 E) k{RX]2[B] 25) In which of the following reactions can alcohol participate? I) oxidation reactions II) elimination reactions III) amide synthesis IV) peptide synthesis V) ester synthesis A) I), III) and V) B) I), II) and V) C) II), III) and V) D) I), II) and IV) E) II), III) and IV) 26) What is a dehydration reaction? A) Dehydration is elimination of water molecule from an alcohol molecule to produce alkene. B) Dehydration reaction is removal of one equivalent of H2 from an alkane to produce alkene. C) Dehydration reaction is one of the steps in chain-reaction polymerization. D) Dehydration reaction is removal of crystalline water. E) Dehydration reaction is deprotonation of a substrate with a strong base in E2 mechanism. 27) Which of the following roles can alcohols have in organic reactions? I) electrophile II) solvent III) base IV) substrate V) acid A) II), III) and IV) B) I), II), and III) C) I), III) and V) D) II), III) and V) E) II), IV) and V) 28) What product would you expect to obtain from a reaction between one isomer of 3-methyl-1-pentanol and HI? A) a substitution product with retention of configuration B) only one elimination product C) a substitution product with inversion of configuration D) two elimination products E) a racemic mixture of substitution products 29) Which of the following is an unsymmetrical reagent? A) Cl2 B) H2O C) H2O and HCl D) HCl E) I2 30) Markovnikof's rule predicts that when HBr is added to an unsymmetrical alkene or alkyne, the H atom will add to which carbon atom? A) the carbon with the fewest attached hydrogens B) the carbon with the Br C) the carbon with the most attached hydrogens D) the carbon next to the double or triple bond E) HBr does not react with unsymmetrical alkenes or alkynes.

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