The exam will be available at 10:00 Wednesday 3/25 on the course Blackboard site under "Assignments". Once you start the exam, you will have 80 minutes to complete all 33 multiple-choice questions. The questions will appear in random order, one at a time, and it will not be possible to revisit a question once you submit an answer.The exam will not be available after 11:45 on Wednesday. If you start at 10:00, your exam will automatically end at 11:20. If you start at 10:10, your exam will end at 11:30. If you start at 11:30, you will only have 15 minutes to complete it because the testing period will end at 11:45.
This is an open book test. You can consult your notes and/or the textbook, but you will need to work quickly to finish 33 questions in 80 minutes. It would be best to be fully prepared so it is not necessary to spend any time reading through the book. You cannot consult with another person during the exam, and you cannot search the internet for answers (the exam may even include a "lock-down browser" feature to hamper internet usage during the testing period).
Be sure to know how to identify the functional groups in the table below, and know how to name them. You will not need to know how to name thiols or amides.Knowing nomenclature will be very important for the exam. The Blackboard multiple-choice test will not have structures drawn, so you will need to be quick with nomenclature and know condensed structural formulas.
For example, CH3COOH is ethanoic acid, CH3COOCH3 is methyl ethanoate (an ester), and CH3CONH2 is an amide.
Also be sure to know the structures corresponding to these special IUPAC names: phenol, benzaldehyde, and benzoic acid.
Functional Group IUPAC Name Common Name Alcohols Yes No Ethers No Yes Aldehydes Yes No Ketones Yes No Thiols No No Carboxylic Acids Yes No Carboxylate Salts Yes No Esters Yes No Amines No Yes Amides No No
Functional Group Transformations
Most of the reactions can be viewed as transformations of functional groups. For example, oxidation of a primary alcohol gives a carboxylic acid, and oxidation of a secondary alcohol gives a ketone.
- Oxidation of primary and secondary alcohols (Ch 14)
- Dehydration of alcohols to make alkenes (Ch 14)
- Dehydration of alcohols to make ethers (Ch 14)
- Oxidation thiols to make disulfides (Ch 14)
- Preparation of esters (Ch 15)
- Hydrolysis of esters under acidic conditions (H+ catalyst)(Ch 15)
- Hydrolysis of esters under basic conditions (NaOH(aq)) (Ch 15)
- Preparation of amides (Ch 15)
- Hydrolysis of amides (Ch 15)
Acid-Base Reactions
Some of the reactions involve the transfer of a proton (H+, the nucleus of a hydrogen atom. You need to be familiar with hydronium ion (H3O+), hydrochloric acid (HCl), and sodium hydroxide (NaOH).
- Ionization of an acid (water + HCl, phenol, or a carboxylic acid)
- Neutralization of an acid (acid + base)
- Reactions of amines with an acid
In sorting out boiling points and water solubilities, the key is to understand the relative strengths of intermolecular forces. For small molecules, dispersion forces (from overlapping electron clouds) are the weakest and hydrogen bonding is the strongest. Among simple compounds that can participate in hydrogen bonding, the interaction is strongest for carboxylic acids.Polar molecules and those with hydrogen-bonding capabilites tend to be more water soluble ("like dissolves like").
Look over your class notes (and the text book) to understand a few special topics. These include alkaloids, flavors and odors, anesthetics, and saponification.
Items not covered are listed below.
Glycols and glycerols (section 14.6) Sodium carbonate and sodium bicarbonate (in Ch 15) Lithium or potassium salts (in Ch 15) Condensation polymers and polyamides (in Ch 15) Esters of phosphoric acid (section 15.10) Names for ammonium ions (but know what an ammonium ion is) Names for amides (but know the structure of an amide) Any problems involving aniline (in Ch 15)