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Theory and Portfolio (10%) - completed individually

Organic Chemistry by Solomons, Fryhle and Synder - 12th edition

Active-learning Questions (completed individually)

  1. Complete the following table below which compares the nucleophilic addition mechanism of aldehydes and ketones and the nucleophilic addition–elimination mechanism of acyl compounds.

Nucleophilic addition reactions
of aldehydes and ketones
(Chapter 16)		Nucleophilic addition–elimination reactions
of acyl compounds
(carboxylic acids and their derivatives)
(Chapter 17)
A. General description of the reaction. Describe the reaction in general and its importance  (maximum 2-3 explanatory points).
B. Provide the general reaction and the general mechanism. Name the mechanistic steps. 
C. Does nucleophilic addition occur? Why? There are three reasons. 
D. In general, when the addition product is stable,  does elimination occur? Why? Omit dehydration reactions talked about in section 16.6C.
E. What is the overall order of reactivity of the substrates? Why?
F. Products formed

Portfolio Questions (completed individually)
  1. Provide product(s) at all steps of the following reaction sequences:
    1. Benzene reacts with
      1. chloromethane in the presence of AlCl3
      2. KMnO4 conc., HO-, hot
      3. H3O+
      4. SOCl2
    2. 1-bromobutane reacts with
      1. NaCN
      2.  H2O, H2SO4
      3. isobutyl alcohol (xs), H2SO4 (cat.)
    3. Bromocyclopentane reacts with
      1. Mg, dry Et2O
      2. CO2
      3. H3O+
      4. LiAlH4, dry Et2O
      5. H3O+
    4. Benzyl alcohol reacts with
      1. H2CrO4, acetone
      2.  SOCl2
      3. dimethylamine (xs)
    5. Phthalamic acid reacts
      1. in the presence of heat
      2.  NaOH, H2O (xs), heat
    6. (R)-2-Bromobutane reacts with
      1. sodium propanoate
      2. NaOH, H2O
    7. Benzoyl chloride reacts with
      1. butyl  lithium (xs), dry Et2O
      2. H3O+
    8. Prop-2-en-1-ol reacts with
      1. PCC, CH2Cl2
      2. CH3OH (xs), HA
      3. KMnO4, HO-, dilute, cold
      4. H3O+
      5. NaBH4, H2O
    9. 4-Bromobutanal reacts with
      1. HOCH2CH2OH, HA
      2. Mg, dry Et2O
      3. CH3CHO
      4. H3O+
      5. CH3OH, HA
    10. Benzene reacts with
      1. ethanoyl chloride, AlCl3
      2. H3O+
      3. SO3, H2SO4
      4. Br2, FeBr3
      5. ethylamine, HA (cat.)
    11. Benzene reacts with
      1. Br2 / FeBr3
      2. Li, dry Et2O
      3. CuI (Corey-House reaction sequence), Section 21.6E, Gilman reagent-mediated couplings
      4. butanoyl chloride
      5. hydrazine / NaOH / heat

  2. You wish to prepare isoamyl acetate (banana flavor) from an alcohol and a carboxylic acid derivative. What method provides the best yield?  Why? Do not forget to provide the complete reaction. 

Chapter 16 Aldehydes and Ketones: Nucleophilic addition to the carbonyl group 
SectionSubject
16.6 Nucleophilic addition to the carbon-oxygen double bond
16.7The addition of alcohols: Hemiacetals and acetals
16.8The addition of primary and secondary amines
16.9The addition of hydrogen cyanide: Cyanohydrins
Chapter 17 Carboxylic Acids and Their Derivatives. Nucleophilic Addition – Elimination at the Acyl Carbon
SectionSubject
17.1Introduction
17.2Nomenclature and physical properties
17.3Preparation of carboxylic acids
17.4Acyl substitution: Nucleophilic addition – elimination at the acyl carbon
17.5Acyl chlorides
17.6Carboxylic acid anhydrides
17.7Esters
17.8Amides
17.12Summary of the reactions of carboxylic acids and their derivatives
Chapter 23 Lipids
SectionSubject
23.1Introduction
23.2Fatty acids and triacylglycerols (omit 23.2E)