Chapter 4 — Quiz
Twenty-five questions. Functional-group recognition, IUPAC nomenclature basics, classification of alcohols/amines.
1. A functional group with structure $-COOH$ is: (a) an aldehyde (b) a ketone (c) a carboxylic acid (d) an ester
2. The suffix -ol designates: (a) an aldehyde (b) a ketone (c) an alcohol (d) an ester
3. In IUPAC nomenclature, the highest-priority functional group becomes: (a) a prefix (b) the suffix (c) ignored (d) written in italic
4. Which has highest priority in IUPAC suffix selection? (a) aldehyde (b) alcohol (c) carboxylic acid (d) ketone
5. The name of $CH_3CH_2CH_2OH$ is: (a) methanol (b) ethanol (c) 1-propanol (d) 2-propanol
6. The name of $(CH_3)_2CHOH$ is: (a) propanol (b) 1-propanol (c) 2-propanol (d) isobutanol
7. A secondary alcohol has: (a) 1 carbon attached to the C-OH carbon (b) 2 carbons attached to the C-OH carbon (c) 3 carbons attached (d) An N-H bond adjacent
8. In $CH_3CO_2CH_2CH_3$, the ester is named: (a) ethyl acetate (b) methyl propanoate (c) ethyl propanoate (d) acetaldehyde
9. An amide contains: (a) $C-OH$ (b) $C-O-C$ (c) $C-NR_2$ directly bonded to a carbonyl (d) $C=N$
10. An aromatic hydroxyl is called a: (a) alcohol (b) ether (c) phenol (d) amine
11. The compound $CH_3-CH_2-O-CH_2-CH_3$ is: (a) propanol (b) butanol (c) diethyl ether (d) methyl propyl ether
12. A nitrile has the structure: (a) $C=N$ (b) $C \equiv N$ (c) $C-NH_2$ (d) $N=O$
13. A chiral center (stereocenter) is: (a) Any double bond (b) Any carbon with four bonds (c) A carbon with four different groups attached (d) An $sp^2$ carbon
14. The compound $CH_3COCl$ is: (a) ethyl chloride (b) acetyl chloride (c) chloroacetic acid (d) methyl chloroacetate
15. The functional group $-SH$ is called: (a) sulfonyl (b) sulfate (c) thiol (d) sulfide
16. A tertiary alcohol is oxidized to: (a) aldehyde (b) ketone (c) carboxylic acid (d) cannot be easily oxidized (no α-hydrogen on O)
17. In the compound 3-methylbutan-2-ol, the -OH is on which carbon? (a) C1 (b) C2 (c) C3 (d) C4
18. Which IUPAC name corresponds to a compound with two C=O groups at positions 2 and 5 of a six-carbon chain? (a) hexan-2,5-dione (b) 2-methylhexan-5-one (c) hexan-2-ol-5-one (d) 2,5-dihydroxyhexane
19. A primary amine has: (a) 0 organic groups on N (b) 1 organic group on N (i.e., RNH₂) (c) 2 organic groups on N (d) 3 organic groups on N
20. Aspirin (acetylsalicylic acid) contains: (a) only a carboxylic acid group (b) a phenol (c) an ester and a carboxylic acid (d) an amide
21. The functional group $-NO_2$ on a ring (e.g., nitrobenzene) is: (a) strongly electron-donating (b) strongly electron-withdrawing (c) neither donor nor acceptor (d) a leaving group in SN2
22. The most acidic functional group listed below: (a) alcohol (pKa ~16) (b) phenol (pKa ~10) (c) carboxylic acid (pKa ~5) (d) thiol (pKa ~10)
23. Tosylate (Ts), mesylate (Ms), and triflate (Tf) are all: (a) functional groups bearing nitrogen (b) sulfonate esters used as excellent leaving groups (c) types of amides (d) protecting groups for amines
24. A primary amine reacting with an aldehyde gives: (a) an amide (b) an imine (c) an amino alcohol (d) an enamine
25. Common bioisosteres for the carboxylic acid group include: (a) tetrazole and sulfonamide (b) ester and ether (c) ketone and aldehyde (d) thiol and sulfide
Answers
| # | Answer | Explanation |
|---|---|---|
| 1 | c | -COOH is the carboxylic acid group |
| 2 | c | -ol = alcohol suffix |
| 3 | b | Highest priority becomes the suffix |
| 4 | c | Carboxylic acid > aldehyde > ketone > alcohol |
| 5 | c | 1-propanol (3-carbon chain, OH at C1) |
| 6 | c | Isopropanol = 2-propanol |
| 7 | b | 2° alcohol: 2 C's on the C-OH |
| 8 | a | Acetate (ethanoate) ester of ethanol |
| 9 | c | Amide: C(=O)-NR₂ |
| 10 | c | Ar-OH = phenol |
| 11 | c | Diethyl ether (Et-O-Et) |
| 12 | b | Nitrile: C≡N |
| 13 | c | 4 different groups = chiral center |
| 14 | b | Acetyl chloride (an acid chloride) |
| 15 | c | -SH = thiol |
| 16 | d | 3° alcohol has no H on the C — can't be oxidized to ketone/aldehyde |
| 17 | b | "an-2-ol" = OH on C2 |
| 18 | a | -2,5-dione: two C=O at positions 2 and 5 |
| 19 | b | 1° amine: RNH₂ (one R) |
| 20 | c | Aspirin: ester + carboxylic acid + aromatic |
| 21 | b | -NO₂ is electron-withdrawing (Ch 22) |
| 22 | c | Carboxylic acid is the most acidic listed (pKa ~5) |
| 23 | b | Sulfonate esters; excellent SN/E leaving groups |
| 24 | b | Imine = R₂C=NR; via condensation from R-NH₂ + RCHO |
| 25 | a | Tetrazole and sulfonamide are common -COOH bioisosteres |
Scoring: 22+ = ready to proceed. 17–21 = re-read the functional-group table. Below 17 = re-read the chapter; nomenclature is a prerequisite for everything that follows.
Concept connections
- Functional groups predict reactivity: alcohols → SN/E; carbonyls → addition; amines → bases/nucleophiles; aromatics → EAS/SNAr.
- Suffix priority (the only ordering you must memorize): COOH > COOR > CONR₂ > CN > CHO > C=O > OH > NH₂.
- The 4 anchor drugs (aspirin, ibuprofen, acetaminophen, thalidomide) illustrate the variety of functional groups in real medicines.
- Spectroscopy connects to functional groups: every group has a characteristic IR/NMR signature (Ch 6, 9).
- Industrial relevance: petrochemistry organizes around functional-group taxonomy.