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Identify the tertiary alcohol(s). CH3CH2CHCH(CH3)2 CH3CHCH2CH(CH3)2 CH3CH2CH2C(CH3)2 OH OH A only A only B only C both A and C B A) B) C) D) 2. A) B) C) D) What is the hybridization of the oxygen atom in alcohols? sp sp sp2 sp3 1. OH C 3. What is the nucleophile in the following substitution reaction? (CH3)3COH + HBr (CH3)3CBr + H2O A) B) C) D) 1) (CH3)3COH is 1 is 2 is 3 is 4 2) (CH3)3C 3) Br 4) H 4. What are the products of the following reaction? CH3CH2CH2CH2OH + HBr A) 1-bromobutane and water B) 1-bromobutane and hydrogen C) butane and HOBr + hydrogen D) CH3CH2CH2CH2OBr Page 1 5. Arrange the following alcohols in order of their decreasing reactivity with HBr (most reactive first). CH2OH CH3 OH HC 3 OH A) B) C) D) A A>B>C A>C>B C>A>B B>C>A B C 6. What is the product of the following reaction? → A) ClCH2CH2CH2CH2OH B) ClCH2CH2CH2CH2Cl C) BrCH2CH2CH2CH2Cl D) ClCH2CH2CH2CH2SOCl BrCH2CH2CH2CH2OH + SOCl2 7. Which of the following undergoes a substitution reaction with sodium cyanide in DMSO at the fastest rate? A) CH3CH2F B) CH3CH2Cl C) CH3CH2Br D) CH3CH2I 8. The rate law for the following reaction is: DMSO CH3CH2CH2Cl + NaCN A) rate = k[CH3CH2CH2Cl] B) rate = k[CH3CH2CH2Cl][NaCN] C) rate = k[CH3CH2CH2Cl][NaCN]2 D) rate = k[CH3CH2CH2Cl]2[NaCN] 9. A) B) C) D) Which of the following reacts the fastest by the SN2 mechanism? CH3Br CH3CH2Br (CH3)2CHBr (CH3)3CBr Page 2 10. Which halide ion reacts the fastest with cyclopentyl p-toluenesulfonate in ethanol/water? OTs A) B) C) D) 1) Iis 1 is 2 is 3 is 2 2) Br- 3) Cl- 4) F- 11. Which of the following reacts fastest with methanol by the SN1 mechanism? CH3 1) CH3CH2CH2CH2CH2Br 3) CH3CCH2CH3 Br 2) CH3CH2CHCH2CH3 4) (CH3)3CCH2Br Br A) B) C) D) is 1 is 2 is 3 is 2 12. A) B) C) D) A pentacoordinate carbon is a transient species in the _____ mechanism. SN1 SN2 E1 E2 Page 3 13. Which of the following reacts the slowest with sodium cyanide, NaCN? 1) OTs 2) A) B) C) D) OTs 3) OTs 4) OTs is 1 is 2 is 3 is 4 14. Which of the following conditions favor the SN1 mechanism as opposed to the SN2 mechanism? (A) tertiary alkyl halide (B) primary alkyl halide (C) polar solvent A) only A B) only B C) A and C D) B and C 15. Rank the following in decreasing order of leaving group ability. O O H3C S O CH3CO Cl OH B C D O A) B) C) D) A A>C>D>B A>C>B>D C>B>A>D B>A>C>D Page 4 16. In which of the solvents below would the reaction shown take place at the fastest rate? CH3CH2CH2CH2CN + NaBr CH3CH2CH2CH2Br + NaCN A) ethanol B) acetic acid C) dimethyl sulfoxide D) water 17. Which of the following undergoes SN1 solvolysis in ethanol/water at the fastest rate? O OTs A) B) C) D) 1) is 1 is 2 is 3 is 4 F Br 2) 3) Page 5 OCCH3 4) Answer Key 1. 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. 13. 14. 15. 16. 17. C D C A B C D B A A C B B C B C A Page 6