2010 fall che 230 chapter 2 homework

ILLINOIS STATE UNIVERSITY
Organic Chemistry 1, CHE 230, fall semester 2010, Homework #2
Chapter 2: Structure and Reactivity
Write out the dissociation expression for acetic acid (CH3CO2H). Write out the Ka expression for the above equilibrium. Provide a rationale for why acetic acid (CH3CO2H) is more acidic than ethanol (CH3CH2OH). 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Provide a reasonable definition for the terms Lewis Acid. Provide a reasonable definition for the terms Lewis Base. Identify the following molecules as either Lewis acids (A), Lewis bases (B) or as neither (N). Consider the following reaction and answer the questions below. What orbital on carbon is accepting the electron density? What is the name given to this type of bond? 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Complete the following reactions. Identify the Lewis acid and the Lewis base. Show the flow of electron density and draw the product. Provide a rationale for why hydroiodic acid (HI) is more acidic than hydrofluoric acid (HF). Provide a rationale for why ammonia (NH3) is more acidic than methane (CH4). 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 One substance has a pKa of -12 and another substance has a pKa of +12. Which one of these acids is the strongest acid? What is the basis for your answer? Determine which side of the equilibrium is favored in the following reactions. Also determine the magnitude of the equilibrium. The pKa value for the amine is 35. The pka of butane is 55. Determine which side of the equilibrium is favored in the following reactions. Also determine the magnitude of the equilibrium. The pKa value for the alcohol is 18. The pka of the carboxylic acid is 5. Determine if the following molecules are Lewis acids, Lewis bases, or neither. 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Write in the letter that corresponds to the functional group in the following series of molecules. 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Rozerem (ramelteon) is described as an orally hypnotic drug used to help people have trouble
sleeping. Determine the molecular formula and identify all of the functional groups that are
present and their mode of reactivity.
Molecular weight:__________________________ Albuterol (ventolin HFA) is a relatively selective beta2-adrenergic bronchodilator. Determine
the molecular formula and identify all of the functional groups that are present and their mode of
reactivity.
Molecular weight:__________________________ 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Detrol LA (tolterodine) is a synthetic agent used to control urinary incontinence. Determine
the molecular formula and identify all of the functional groups that are present and their mode of
reactivity.
Molecular weight:__________________________ Propecia (finasteride) is a synthetic 4-azasteroid that is a specific inhibitor of steroid Type II
5α-reductase. Propecia is a relatively selective beta2-adrenergic bronchodilator. Determine the
molecular formula and identify all of the functional groups that are present and their mode of
reactivity.
Molecular weight:__________________________ 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Crestor (rosuvastatin) is a synthetic lipid lowering agent prepared by AstraZeneca.
Rosuvastatin is an inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG coA) reductase.
Determine the molecular formula and identify all of the functional groups that are present and
their mode of reactivity.
Molecular weight:__________________________ Lipitor (atorvastatin) is a synthetic lipid lowering agent prepared by Pfizer. Atorvastatin is an
inhibitor of 3-hydroxy-3-methylglutaryl-coenzyme A (HMG coA) reductase. Determine the
molecular formula and identify all of the functional groups that are present and their mode of
reactivity.
Molecular weight:__________________________ 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Draw out at least four (4) constitutional isomers for hexane. Name the following molecules. You may use either systematic nomenclature or common names. Describe in detail what is wrong with the names for the following molecules. 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Provide systematic IUPAC names for the following side chains. Provide a reasonable name for the molecules that are depicted below: 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Provide a reasonable name for the molecules that are depicted below: Simple Branching
2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Provide a reasonable name for the molecules that are depicted below: Complex Branching
Provide names for the following molecules. Two boxes are provided. Use the first box
for the systematic branch name; use the other for the branch common name.
2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Draw the Newman projections of the least stable and most conformers of ethane along the 1,2 bond. Least stable
Most stable
Draw the Newman projections of the least stable and most conformers of butane along the 2,3 bond. Least stable
Most stable
Draw the Newman projections of the least stable and most conformers of 2,2-dimethylbutane along the 2,3 bond. Least stable
Most stable
2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Draw the Newman projections of the least stable and most conformers of n-hexane along the 3,4-bond. Least stable
Most stable
Draw the Newman projections of the least stable and most conformers of 2,2,3,3-tetramethylbutane along the 2,3 bond. Least stable
Most stable
2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160 Write in the name that best describes the conformers that are drawn below. Which structure is most likely dominant in solution at room temperature?__________________ Which structure is most likely in very low concentration at room temperature?______________ Which structure has the greatest torsional strain?______________________________________ Which structure has the least amount of torsional strain?________________________________ Identify two structures that have the same amount of potential energy _____________________ 2010 Assoc. Prof. S. R. Hitchcock, Department of Chemistry, Illinois State University, Normal, IL 61790-4160

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