Chapter 1 — Quiz

Twenty questions for self-assessment. Answers at the bottom. Do not scroll ahead.

1. Which of the following was not one of Berzelius's defining claims about organic chemistry? (a) Organic compounds are produced only by living systems. (b) Organic compounds cannot be synthesized from inorganic starting materials. (c) A "vital force" is required to produce organic compounds. (d) Organic compounds contain carbon.

2. Wöhler's 1828 synthesis of urea from ammonium cyanate is significant because: (a) It was the first synthesis of any organic compound. (b) It produced urea for the first time in history. (c) It showed that an "organic" compound could be made from "inorganic" starting materials. (d) It proved that all organic compounds can be synthesized from $CO_2$.

3. The modern definition of organic chemistry is: (a) The chemistry of compounds produced by living systems. (b) The chemistry of compounds whose principal skeleton is built from carbon. (c) The chemistry of compounds that contain carbon-hydrogen bonds. (d) The chemistry of compounds that contain both carbon and hydrogen.

4. Carbon's ground-state electron configuration is: (a) $[He]2s^{2}2p^{4}$ (b) $[He]2s^{2}2p^{3}$ (c) $[He]2s^{2}2p^{2}$ (d) $[He]2s^{1}2p^{3}$

5. Which feature of carbon is not cited in Chapter 1 as a reason for carbon's uniqueness? (a) Tetravalency. (b) Strong $\sigma$ and $\pi$ bonds. (c) High electronegativity (above that of oxygen). (d) Catenation (ability to bond to itself indefinitely).

6. The $C-C$ bond dissociation energy is approximately: (a) 35 kcal/mol (b) 53 kcal/mol (c) 83 kcal/mol (d) 200 kcal/mol

7. Compared to the $C=C$ bond, the $Si=Si$ bond is: (a) Stronger and more common in biology. (b) Similar in strength. (c) Much weaker, which is why silicon does not form stable $\pi$-bonded molecules. (d) Not possible to form at all.

8. How many constitutional isomers of $C_4H_{10}$ exist? (a) 1 (b) 2 (c) 3 (d) 4

9. The geometry of a saturated ($sp^3$-hybridized) carbon is: (a) Linear, 180° bond angles. (b) Trigonal planar, 120° bond angles. (c) Tetrahedral, 109.5° bond angles. (d) Octahedral, 90° bond angles.

10. A chiral carbon has: (a) A single hydrogen atom. (b) Four different groups attached. (c) Two identical groups and two different ones. (d) A $\pi$ bond.

11. The two enantiomers of thalidomide differ in: (a) Their molecular formulas. (b) Their connectivity of atoms. (c) The three-dimensional arrangement of bonds at one carbon. (d) The number of chiral centers they contain.

12. The four primary skills Chapter 1 identifies for the organic chemistry course are: (a) Memorizing reactions, balancing equations, computing yields, and writing lab reports. (b) Drawing structures, predicting reactivity, designing syntheses, and interpreting spectra. (c) Naming compounds, knowing named reactions, computing $pK_a$, and doing chromatography. (d) Working in groups, taking careful notes, attending office hours, and finishing problem sets.

13. Retrosynthetic analysis is the skill of: (a) Running a reaction backward to recover starting materials. (b) Designing a synthesis by working backward from a target to simpler precursors. (c) Analyzing the spectrum of a product to confirm structure. (d) Computing the thermodynamics of a synthesis.

14. In the $S_{N}2$/$S_{N}1$/$E2$/$E1$ decision framework, which factor does not appear? (a) The substrate (primary, secondary, tertiary). (b) The nucleophile or base (strong, weak, bulky). (c) The solvent (polar protic or aprotic). (d) The molecular weight of the substrate.

15. Approximately how many distinct organic compounds are registered in the Chemical Abstracts Service (CAS) database? (a) 1 million (b) 10 million (c) 210 million (d) 2 billion

16. Aspirin, ibuprofen, and acetaminophen all share the functional group / feature: (a) An ester group. (b) A chiral carbon. (c) A six-membered aromatic ring (benzene). (d) A carboxylic acid.

17. Sodium borohydride ($NaBH_4$) reduces an aldehyde to: (a) A ketone. (b) A primary alcohol. (c) A carboxylic acid. (d) An alkene.

18. Vitalism is best described as: (a) A chemical theory, still valid today, that explains enzyme catalysis. (b) A nineteenth-century doctrine that organic compounds require a "vital force" to be synthesized. (c) A modern term for the study of biomolecules. (d) A method for distinguishing organic from inorganic compounds in the laboratory.

19. The mechanism-first approach to organic chemistry, as this book argues, is superior to the functional-group-first approach because: (a) It is easier to memorize. (b) It produces higher test scores. (c) It teaches a smaller number of principles that can be used to derive many reactions. (d) It is the approach favored by most introductory textbooks.

20. Thalidomide has been recently rehabilitated as the scaffold for: (a) A new class of antibiotics. (b) A new class of statins (cholesterol-lowering drugs). (c) A new class of targeted protein degraders (PROTACs) used in cancer therapy. (d) A new class of antivirals for influenza.

Answer key

  1. (d) — Vitalism pre-dated our modern structural understanding, so Berzelius did not claim organic compounds contain carbon per se; he claimed they required a vital force. (Carbon was the observed commonality, not the definition.)
  2. (c)
  3. (b)
  4. (c)
  5. (c) — Carbon's electronegativity is moderate (2.55), below oxygen's (3.44).
  6. (c)
  7. (c)
  8. (b) — n-butane and isobutane (2-methylpropane).
  9. (c)
  10. (b)
  11. (c)
  12. (b)
  13. (b)
  14. (d)
  15. (c)
  16. (c)
  17. (b)
  18. (b)
  19. (c)
  20. (c)

Scoring guide: - 18–20 correct: You are ready for Chapter 2. - 14–17 correct: Re-read any section where you missed a question. - 10–13 correct: Re-read the whole chapter more slowly, with notes. - Below 10: Read the chapter again. Do not proceed to Chapter 2 yet.