Organic Chemistry by Solomons, Fryhle and Synder 11th and 12th editions
Chapter 14 Aromatic compounds

Active-learning Questions (completed individually)

  1. Describe the structure of benzene in terms of the two theories provided.
  2. Why is the benzene molecule more stable than simply the hypothetical 1,3,5-cyclohexatriene?
  3. What is Hückel’s rule? Describe, with the use of an example, the four (4) criteria a compound must possess to be considered aromatic? Omit the polygone method. 
  4. Choose one (1) example of an aromatic compound from among the following: benzenoid aromatic compounds, graphite, fullerene, carbon nanotubes, heterocyclic aromatic compounds, and aromatic compounds in biochemistry.  Describe its structure and its importance/significance. Each team must choose a different example and will give their explanation to the class on the white board.

Portfolio Questions (completed individually)

  1. How do the ultraviolet rays (all together) affect our DNA at the molecular level? Provide one (1) negative AND one (1) positive physiological effect of the ultraviolet rays (UVA or UVB).
  2. List the active sun-blocking ingredients in the sunscreen Ombrelle kids SPF 50+ water resistant (40 min).
    1. These ingredients can be divided into general two categories. What are they and how does each perform their function?
    2. For each organic ingredient:
      1. Draw its structure and indicate whether it protects against the UVA or UVB rays. 
      2. Indicate its wavelength of maximum absorbance (Lambdamax).
      3. Identify and provide the name the different classes of organic compounds present in the molecules (e.g. 1° aliphatic alcohol), as well as the conjugated unsaturated regions (circle it with a different color).
      4. Indicate its EWG score. Environmental Working Group (EWG) has created a Skin Deep Cosmetics Database (https://www.ewg.org/skindeep/) to allow us to protect ourselves from everyday exposures to chemicals in many cosmetics and personal care products.  Its score helps to assess the potential hazards and health concerns for many ingredients and products. 
      5. Provide one health concern or risk.
    3. You may find useful information on PubChem (https://pubchem.ncbi.nlm.nih.gov/) and Drugbank (https://www.drugbank.ca/).
  3. How are sunscreens an application of the three important concepts: aromatic systems, conjugated unsaturated systems, as well as UV-Vis spectroscopy?
SectionSubject
14.1The discovery of benzene
14.2Nomenclature of benzene derivatives
14.3Reactions of benzene
14.4The Kekulé structure for benzene
14.5The thermodynamic stability of benzene
14.6Modern theories of the structure of benzene (omit Figure 14.4)
14.7Hückel’s rule: The 4n + 2 electron rule (omit 14.7A, C, D, E)
14.8Other aromatic compounds (read only)
14.9Heterocyclic aromatic compounds (read only)
14.10Aromatic compounds in biochemistry (read only)
14.11Spectroscopy of aromatic compounds (omit 14.11 A, B, E)
The chemistry of…Sunscreens (catching the sun’s rays and what happens to them) – p 656 (11th edition), p 648 (12th edition)