Exam Study Notes for Chemistry 242-0004

Examination Information

  • Institution: James Madison University
  • Course: Chemistry 242-0004 Organic Chemistry II
  • Semester: Spring Semester 2025
  • Date: March 30, 2026
  • Instructor: Chris Hollinsed, Ph.D.
  • Exam Type: Exam 3P
  • Chapters Covered:
    • Chapter 12, 13: Alcohols and Ethers (Objective 5)
    • Chapter 19: Aldehydes and Ketones (Objective 6)

Periodic Table of Elements

  • List of selected elements with their atomic numbers and atomic masses:
    • H (Hydrogen): Atomic Number = 1, Atomic Mass = 1.00
    • He (Helium): Atomic Number = 2, Atomic Mass = 4.00
    • Li (Lithium): Atomic Number = 3, Atomic Mass = 6.94
    • Be (Beryllium): Atomic Number = 4, Atomic Mass = 9.01
    • B (Boron): Atomic Number = 5, Atomic Mass = 10.8
    • C (Carbon): Atomic Number = 6, Atomic Mass = 12.0
    • N (Nitrogen): Atomic Number = 7, Atomic Mass = 14.0
    • O (Oxygen): Atomic Number = 8, Atomic Mass = 16.0
    • F (Fluorine): Atomic Number = 9, Atomic Mass = 19.0
    • Ne (Neon): Atomic Number = 10, Atomic Mass = 20.1
    • Na (Sodium): Atomic Number = 11, Atomic Mass = 22.9
    • Mg (Magnesium): Atomic Number = 12, Atomic Mass = 24.3
    • Al (Aluminum): Atomic Number = 13, Atomic Mass = 26.9
    • Si (Silicon): Atomic Number = 14, Atomic Mass = 28.0
    • P (Phosphorus): Atomic Number = 15, Atomic Mass = 30.9
    • S (Sulfur): Atomic Number = 16, Atomic Mass = 32.0
    • Cl (Chlorine): Atomic Number = 17, Atomic Mass = 35.4
    • Ar (Argon): Atomic Number = 18, Atomic Mass = 39.9
    • K (Potassium): Atomic Number = 19, Atomic Mass = 39.1
    • Ca (Calcium): Atomic Number = 20, Atomic Mass = 40.0
    • Sc (Scandium): Atomic Number = 21, Atomic Mass = 44.9
    • Ti (Titanium): Atomic Number = 22, Atomic Mass = 47.8
    • V (Vanadium): Atomic Number = 23, Atomic Mass = 50.9
    • Cr (Chromium): Atomic Number = 24, Atomic Mass = 52.0
    • Mn (Manganese): Atomic Number = 25, Atomic Mass = 54.9
    • Fe (Iron): Atomic Number = 26, Atomic Mass = 55.8
    • Co (Cobalt): Atomic Number = 27, Atomic Mass = 58.9
    • Ni (Nickel): Atomic Number = 28, Atomic Mass = 58.6
    • Cu (Copper): Atomic Number = 29, Atomic Mass = 63.5
    • Zn (Zinc): Atomic Number = 30, Atomic Mass = 65.3
    • Subsequent elements continue with respective atomic numbers and masses until 118.

Alcohols and Ethers (Chapters 12, 13, Objective 5)

Reagent Sequences

  1. Choose the correct sequence of reagents for each transformation:

    • A. 1) TMSCl, pyridine
      2) KOt-Bu
      3) m-CPBA
      4) NaH
      5) TBAF or H3O+
    • B. 1) TMSCl, pyridine
      2) Mg0
      3) 2-butanone
      4) H3O+
    • C. 1) TMSCl, pyridine
      2) Mg0
      3) acetone
      4) H3O+
    • D. 1) NaH
    • E. 1) NaH
      2) 2-bromobutane
      3) H3O+
    • F. 1) TMSCl, pyridine
      2) KOt-Bu
      3) TBAF
      4) Hg(OAc)2
      5) NaBH4

  2. Expected Product of Reaction:

  3. Reagents for Conversion:

    • A. 1) mCPBA; 2) CH3MgBr; 3) H3O+
    • B. 1) CH3MgBr; 2) H2O
    • C. 1) mCPBA; 2) H2O
    • D. mCPBA
      Note:
  • TMSCl = Trimethylsilyl chloride
  • TBAF = Tetra-n-butyl ammonium fluoride
  • TBAF or H3O+ can be used to deprotect trimethylsilyl groups.

Additional Transformations and Product Selection

  1. Choose the correct product.

  2. Reagents for Other Transformations:

    • A. 1) BH3 THF, 2) H2O2, NaOH, 3) NaH, 4) CH3CH2CH2Br
    • B. 1) HBr, ROOR, 2) NaOCH2CH3
    • C. 1) Hg(OAc)2, CH3CH2OH, 2) NaBH4
    • D. 1) m-CPBA, 2) PCC, 3) CH3CH2MgBr

  3. Choose the correct reagents for various transformations.

    • A. 1) R2BH, 2) H2O2, NaOH, 3) NaBH4, 4) NaH, 5) CH3CH2CH2Br
    • B. 1) Na, liq NH3, 2) HBr, ROOR, 2) NaOCH2CH3
    • C. 1) H2, Lindlar’s cat., 2) m-CPBA, 3) EtMgBr, 4) H3O+
    • D. 1) mCPBA, 2) PCC, 3) CH3CH2MgBr

  4. Select appropriate reagents for further transformations:

    • A. 1) Mg, ether, 2), 3) H3O+, 4) Na2Cr2O7, H2SO4, H2O
    • B. 1) Na, liq NH3, 2) HBr, ROOR, 2) NaOCH2CH3
    • C. 1) Mg, ether, 2), 3) H3O+, 4) Pyridinium chlorochromate (PCC), CH2Cl2
    • D. 1) KOt-Bu, mCPBA, 2) PCC, 3) CH3CH2MgBr

Outcomes Based on Structure

  1. Choose correct products based on given transformations.
    • Structures are referenced but not detailed here.

Aldehydes and Ketones (Chapter 19, Objective 6)

Reactions and Products

  1. Choose the correct product of reaction from given reagents.
  2. Identify reagents appropriate for synthesizing given compounds under the specified conditions:
    • Catalytic amount of acid and water removal conditions.
  3. Determine structures formed from reactions involving catalytic acids and water removal.

Structural Identification

  1. Write structural representations based on the reactions applied.
  2. Identify correct structures that lead to specified products.
  3. Choose combinations leading to the desired compound under specified conditions.

Endnotes

  • Questions 12-21 include multiple choice regarding compound formations related to dehydrations and other reactions involving aldehydes and ketones.
  • Note emphasis on catalytic conditions where water is removed, affecting product outcomes.