CHEM 345 Lesson 9 Problem Set Notes

IUPAC Naming and Structure Drawing

• 9.1 IUPAC Naming

  • Convert structure to IUPAC names; example given includes compounds like HO and CHO.

• 9.2 Structure Drawing

  • Draw chemical structures based on names provided. Names:
  • 3-Methylbutanal:
  • Phenylacetaldehyde:
  • 3-Methyl-3-butenal:
  • cis-3-tert-butylcyclohexanecarbaldehyde:
    • Identify stereochemical relationships in provided structures.
  • 2-(1-chloroethyl)-5-methylheptanal: Analyze for chiral centers.

Reactions and Transformations

• 9.3 Chemical Transformations

  • Discuss multi-step transformations for:
  • Cyclohexene to cyclohexanone
  • 3-hexyne to 3-hexanone
  • Benzene to m-bromoacetophenone
  • Bromobenzene to acetophenone

• 9.4 Structure for Oxidation

  • Draw corresponding alcohols that can be oxidized to form specified aldehydes and ketones.

• 9.5 Completing Reaction Schemes

  • Fill in the missing structures and reagents within provided sequences such as:
  • PhCHO to Alcohol
  • Use reagents like PCC, H2O, t-BuOK, and others.

Classification and Practice

• 9.6 Classify Structures

  • Identify structures as acetals, hemiacetals, or neither through analysis of functional groups.

• 9.7 Acetal Practice

  • Complete the table for various reactions, recording major products, reactants, and conditions.

• 9.8 Reaction Practice

  • Similar to acetal practice, complete reactions with details mentioned.

Enolates and Aldol Reactions

• 9.9 Drawing Enolates

  • Generate all possible enolates from provided carbonyl compounds with resonance forms included.

• 9.10 Aldol Addition Products

  • Predict the aldol addition products from various aldehydes when treated with sodium hydroxide.

• 9.11 Aldol Condensation Products

  • Predictions of products for given aldol reactions identified.

• 9.12 Explanation of Reactions

  • Discuss why 2,2-dimethylbutanal does not undergo aldol addition with sodium hydroxide.

Retrosynthesis and Mechanisms

• 9.13 Aldol Retrosynthesis

  • Analyze aldol condensation products and perform retrosynthesis including:
  • Labeling alpha and beta positions
  • Identifying b-hydroxy carbonyl precursors
  • Indicating donor and acceptor structures

• 9.14 Mechanisms Practice

  • Draw mechanisms for various reactions involving catalysts and reactants.

• Additional Practice

  • Include heat and NaOH steps where applicable, such as aldehydes undergoing specific reactions with water or other reagents.