alcohols, phenols, thiols, Exams of Organic Chemistry

Download alcohols, phenols, thiols and more Exams Organic Chemistry in PDF only on Docsity! Chapter 7 -- Alcohols, Phenols & Thiols 1. Which of the following is a secondary (2°) alcohol? A) I B) II C) III D) IV E) V 2. Which of the following is 3-pentyn-1-ol? A) B) C) D) E) 3. What is the IUPAC name for isobutyl alcohol? A) 1-butanol B) 2-butanol C) 2-methyl-2-butanol D) 2-methyl-1-propanol 4. What would be the IUPAC name for the following alcohol? A) 2-methyl-4-pentanol B) 2-methyl-4-hydroxypentane C) 4-methyl-2-pentanol D) 4-hydroxy-2-methylpentane E) 2-hydroxy-4-methylpentane 5. Which of the following molecules is classified as a tertiary (3°) alcohol? A) I B) II C) III D) IV E) V 6. What is the correct name for the following molecule? A) 2-pentanol B) 3-thiopentanol C) 2-pentanethiol D) 4-pentanethiol E) pentylsulfide 7. What is the name of the following alcohol? D) HCl E) NH3 18. Which of the following phenols is the strongest acid? A) D) B) E) C) 19. Which of the following is the strongest base? A) B) C) D) E) 20. Electron-withdrawing substituents A) increase acidity by increasing the stability of acids. B) decrease acidity by increasing the stability of a conjugate base. C) increase acidity by increasing the stability of a conjugate base. D) decrease acidity by increasing the stability of acids. E) can only have a slight effect on acidity. 21. Phenols are stronger acids than alcohols because of the A) resonance stabilization of phenoxide ions. B) resonance stabilization of phenols. C) resonance stabilization of alkoxide ions. D) resonance stabilization of alcohols. E) hydrogen bonding in phenols. 22. The pKa of an acid whose Ka = 10–11 is A) 1011 B) 11 C) –11 D) 3 E) –3 23. Which of the following alcohols would react most rapidly under SN1 conditions? A) CH3OH B) CH3CH2OH C) (CH3)2CHCH2OH D) (CH3)3COH E) CH3CH2CH2OH 24. Which statement is false? Tert-Butyl alcohol reacts A) with HCl to give 2-methylpropene by an E1 mechanism. B) with HCl to give 2-chloro-2-methylpropane by an SN1 mechanism. C) with HCl and HBr at very different rates. D) with HCl or HBr to give a carbocation intermediate. E) with HCl to give both 2-methylpropene and 2-chloro-2-methylpropane. 25. The rate-determining step in the following reaction is: A) protonation of the alcohol. B) ionization of the alcohol to give a carbocation. C) loss of water from the protonated alcohol to give a carbocation. D) capture of a carbocation by bromide ion. E) displacement of water from the protonated alcohol by bromide ion. 26. The rate-determining step in the following reaction is: A) protonation of the alcohol B) ionization of the alcohol to give a carbocation. C) loss of water from the protonated alcohol to give a carbocation D) capture of a carbocation by bromide ion. E) displacement of water from the protonated alcohol by bromide ion. 27. What type of compound is formed when a secondary (2°) alcohol is treated with Jones' reagent? A) an alkene B) an alkyne C) an aldehyde D) a ketone E) a carboxylic acid 28. When an alcohol reacts with an alkali metal like Na, the product formed is a(n): A) alkene B) alkoxide C) acetylide D) alkane E) hydroxide F) alkyne 29. Which reagents would you use to accomplish the following transformation? A) H2SO4, H2O, acetone B) CrO3, H2SO4, acetone C) PCC/CH2Cl2 D) Zn, HCl, acetone E) H2, Pd, acetone 30. is the major product from the E1 dehydration of 2-methyl-2-hexanol? A) 4-methyl-1-hexene B) 4-methyl-3-hexene C) 2-methyl-2-hexene D) 2-methyl-1-hexene E) 2-methylhexane 31. Which of the following mixtures would NOT react? A) I B) II C) III D) IV E) II and IV 32. What reagents would accomplish the following transformation?