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Chapter 7 -- Alcohols, Phenols & Thiols
- Which of the following is a secondary (2°) alcohol? A) I B) (^) II C) (^) III D) (^) IV E) (^) V
- Which of the following is 3-pentyn- 1 - ol? A) B) C) D) E)
- What is the IUPAC name for isobutyl alcohol? A) (^1) - butanol B) (^2) - butanol C) (^2) - methyl- 2 - butanol D) (^2) - methyl- 1 - propanol
- 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
- Which of the following molecules is classified as a tertiary (3°) alcohol? A) (^) I B) (^) II C) (^) III D) (^) IV E) (^) V
- What is the correct name for the following molecule? A) (^2) - pentanol B) (^3) - thiopentanol C) (^2) - pentanethiol D) 4 - pentanethiol E) (^) pentylsulfide
- What is the name of the following alcohol?
C) CH 3 OH
D) CH 3 SH
E) CH 3 CH 2 NH 2
- Which of the following molecules would have the highest boiling point? A) (^) CH 3 CH 2 OH B) (^) CH 3 OCH 3 C) (^) CH 3 CH 2 Cl D) (^) CH 3 CH 2 CH 3 E) (^) CH 3 CH 2 I
- The expected order of boiling points of the following is: A) (^) 3 > 2 > 1 B) (^) 1 > 2 > 3 C) (^) 1 > 3 > 2 D) (^) 2 > 3 > 1 E) (^) 2 > 1 > 3
- A Lewis acid is a: A) (^) proton donor B) (^) electron pair donor C) (^) electron pair acceptor D) (^) proton acceptor
- The conjugate base of carbonic acid, H 2 CO 3 , is: A) (^) H 3 CO 3 + B) (^) CO 2 C) (^) HCO 3 – D) (^) CO 32 - E) (^) CO 3 –
- If the p Ka of isopropyl alcohol is 17, what is the Ka of isopropyl alcohol? A) (^17) 10 –^17 B) 10 –^17 C) 10 –^3 D) 1017 E) 103 F) (^17) 1017
- Which of the following molecules would be the strongest Brønsted-Lowry acid? A) (^) H 2 O B) (^) CH 4 C) (^) HF
D) (^) HCl E) (^) NH 3
- Which of the following phenols is the strongest acid? A) D) B) E) C)
- Which of the following is the strongest base? A) B) C) D) E)
- 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.
- 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.
- The p Ka of an acid whose Ka = 10–^11 is A) 1011 B) (^11)
- 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
- Which reagents would you use to accomplish the following transformation? A) (^) H 2 SO 4 , H 2 O, acetone B) (^) CrO 3 , H 2 SO 4 , acetone C) (^) PCC/CH 2 Cl 2 D) (^) Zn, HCl, acetone E) (^) H 2 , Pd, acetone
- 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
- Which of the following mixtures would NOT react? A) (^) I B) (^) II C) (^) III D) (^) IV E) (^) II and IV
- What reagents would accomplish the following transformation?
A) (^) 1. PCl 3 2. H 3 O+ B) (^) CrO 3 , H in acetone C) (^) PCC, CH 2 Cl 2 D) (^) 1. Na 2. CH 3 OH E) (^) none of the above
- Acid-catalyzed dehydration of 3-methyl- 3 - hexanol can give the following number of alkenes (including stereoisomers): A) (^2) B) (^3) C) (^4) D) (^5) E) (^6)
- Cyclohexanol and phenol react similarly toward A) (^) sodium hydride. B) (^) FeBr 3 , Br 2. C) (^) conc. H 2 SO 4 , heat. D) (^) PCl 3. E) (^) SOCl 2.
- Oxidation of secondary alcohols with Jones' reagent (CrO 3 , H+, acetone) gives A) (^) carboxylic acids. B) (^) aldehydes. C) (^) ketones. D) (^) chromate esters. E) (^) tertiary alcohols.
- Which of the following reagents will oxidize primary alcohols to carboxylic acids?
- CrO 3 , H 2 SO 4
- PCC
- PCl 3
- SOCl 2 A) (^) only 1 B) (^) only 2 C) (^) only 3 D) (^) only 4 E) (^) 1 and 2
- Which of the following reagents will oxidize secondary alcohols to ketones?
- CrO 3 , H 2 SO 4
- PCC
- PCl 3
- SOCl 2 A) (^) only 1 B) (^) only 2
42. What is the major product of the following reaction?
- A) CH 3 CH 2 CH=CH
- B) cis - CH 3 CH=CHCH
- C) trans - CH 3 CH=CHCH
- D) (CH 3 ) 2 C=CH
