Chem 211 - Exam #1 Sample

Sample Exams are designed to give you an idea of the types of questions you can expect.

Problems for this exam will be very similar to the following problems from the indicated chapters.  However, remember that you are responsible for any material that we have discussed this semester, as well as material from Chem210, as it relates to the current content.  

As you can see, many of the problems come from Chapter 14, which is the main chapter on carboxylic acids.  Good luck.

Sample Problems for Exam #1

Chapter	Problem Numbers
13	None listed but you are responsilble for reactions involving  aldehydes and ketones.
14	2, 3, 4, 5, 7, 8, 9, 10, 11, 12, 14, 16, 20, 22, 24, 25, 31
15	1, 2, 5, 6, 9, 15
16	1, 7, 8

Sample questions from previous exams:

1.  Give structures of any Grignard reagent and any reactant (aldehyde, ketone or ethylene oxide) that would react together to yield each of the following alcohols. If more than one combination of reactions is possible show each of the combinations.

• 1-phenyl-1-propanol
• 2-phenyl-2-propanol
• 1-cyclohexylethanol

2. Describe exactly how you would go about separating a mixture of the three water-insoluble liquids, (a) aminobenzene (b.p. 184^oC), (b) n-butylbenzene (b.p. 183^oC), and (c) n-pentanoic acid (b.p. 187^oC), recovering each compound pure and in essentially quantitative yield.  (Think acid-base concepts.)

2. Describe simple chemical tests that would distinguish between the following. Tell what you would do and see.

• propionic acid and methyl acetate
• acetic anhydride and n-butyl alcohol

3. Starting with n-pentanoic acid, and using any other reagents you need, outline the synthesis of 3-ethyl-3-heptanol via the reaction of a Grignard reagent with: (a) a ketone; (b) an ester.

4. Starting with ethyl acetate, show the reactants and products for the following:

• ammonolysis (reaction with ammonia)
• transesterification with t-butanol
• acid catalyzed hydrolysis
• base catalyzed hydrolysis
• production of any ketone

5. Starting with acetyl chloride show the products of reaction with:

• ammonia
• aminoethane
• aniline
• ethanol

6. Show the reaction necessary to produce succinic anhydride from succinic acid (butanedioc acid).

7. Draw the structures of

• acetic anhydride
• isopentyl acetate
• benzoic acid
• benzoyl chloride
• acetamide
• N,N-dimethyl formamide
• propionyl (propanoyl) chloride
• butyl butyrate
• phenyl methyl ketone

8. Draw resonance structures for each of the following

• carboxylate ion
• carboxylic acid
• p-nitrobenzoate

9. Give names for the following, using either IUPAC or common names:

• 2-carbon acid
• 4-carbon acid
• 3-carbon dicarboxylic acid
• CH₃CH₂CH₂COOCH(CH₃)₂
• CH₃CH₂CH₂COCl
• 2-carbon amide

10. Show a complete reaction mechanism for :

• a nucleophilic addition to a ketone or aldehyde
• nucleophilic substitution to an acid or acid derivative
• a carbanion ion reaction. Include all reactants and products for each type of reaction.