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Review for Exam 2
Introduction to Organic and Biological Chemistry
Fall 2016
Chapter 12: Unsaturated Hydrocarbons
1. Know what an aromatic compound is and the bond angles found there
2. Know how to name aromatic compounds by IUPAC rules.
3. Know the physical properties of aromatics that we discussed
4. Know the chemical properties of aromatic compounds and be able to finish reactions
of the following type:
a. halogenation
b. nitration
c. sulfonation
d. alkylation
e. oxidation of alkylbenzenes
Chapter 13. Alcohols, Phenols, Ethers and their Sulfur Analogues.
1.Know what a functional group is, especially the ones in the chapter
2. Know about the bonding, hybridization, geometry and bond angles for an alcohol
3. Be able to recognize primary, secondary, and tertiary alcohols
4. Be able to name alcohols
5. Understand why alcohols have higher boiling points and better water-solubility than
corresponding alkanes.
6. Know about the chemical reactivity of alcohols
a. Know that alcohols are neutral in water, but can react with strong acid
b. Dehydration in sulfuric acid and high heat (180°) to give double bonds . Be
able to show the major products here.
c. Reaction in sulfuric acid at low heat (140°) to give a symmetrical ether (for
primary alcohols only).
d. Combustion
e. Oxidation with chromic acid or KMnO4. A primary alcohol goes to aldehyde
and secondary goes to ketone. Tertiary does not oxidize.
7. Know about the structure of phenols.
8. Be able to name phenols
9. Phenols are more soluble in water than alcohols because they are more polar. Know
about the chemical reactivity
a. Phenols are acidic in water (carbolic acid)
b. Be able to finish aromatic reactions with phenols. (They do not act like
alcohols in reactions.)
c. Phenols can be oxidized (with O2) to give ketones (hydroxyl quinone to
quinone) and those can be reduced (H2/Pt) to give the phenol...but only if there
are other groups attached to the ring. Remember our discussion of BHT and
other antioxidants.
10. Be able to recognize and name ethers
11. Understand why ethers have similar solubility in water to alcohols, but have much
lower boiling points.
12. Ethers are combustible and used to be used as anesthetics.
13. Be able to recognize and name thiols
14. Know that their odor is disagreeable (think skunk spray )
15. Know the chemical properties of thiols
a. Oxidation of thiols
b. Reduction of thiols
c. Reaction of thiols with heavy metals like lead or mercury.
Chapter 14. Aldehydes and Ketones
1. Be able to recognize and name aldehydes and ketones
2. Know that aldehydes and ketones are functional isomers (constitutional isomers that
involve having different functional groups)
3. Understand why aldehydes and ketones have lower bps than alcohols, but about the
same solubility in water as alcohols.
4. Know the chemical properties of aldehydes and ketones
a. Oxidation with chromic acid, Benedict’s/Fehling’s, or Tollens- aldehydes
oxidize to carboxylic acids, ketones cannot be oxidized.
(Benidict’s/Fehlings works best with an α-hydroxy aldehyde and will also
oxidize an α-hydroxy ketone, as we will see later in the semester) .
b. Reduction with H2/Pt, sodium borohydride (NaBH4 )or lithium aluminum
hydride (LiAlH4) or NAD+- aldehydes reduce to primary alcohols and
ketones to secondary alcohols.
c. Hemiacetal and full acetal formation- aldehydes and ketones react with
alcohols in the presence of an acid to form hemiacetals (hemiketals) with
one mole of alcohol and a full acetal (ketal) with two moles of alcohol.
Chapter 15. Carboxylic acids, Esters, and other Acid Derivatives.
1. Know how to recognize and name carboxylic acids
2. Know that carboxylic acids have higher boiling points than corresponding alcohols
because they can hydrogen bond more (form dimers), but have similar solubility in water.
3. Their odor is disagreeable.
4. Chemical reactivity of carboxylic acids
a. Carboxylic acids are weak acids and will have a low pH in water. Understand
why that is.
b. Know how to make esters from carboxylic acids
and alcohols in the presence of acid including polyesters.
5. Know how to recognize and name carboxylate salts
6. Know that carboxylate salts are solids at RT with high mp and bp because they are
ionic compounds.
7. They are weak bases, preservatives and soaps. Know how soaps clean, what soap
scum is and how to clean it/ avoid it.
8. Be able to recognize and name esters
9. Know that esters will have lower boiling points than corresponding ketones and
aldehydes, but will have similar water-solubility
10. Esters smell good; usually fruity or minty
11. Know how to hydrolyze esters in acid and in base.
12. Recognize acid halides and acid anhydrides and be able to name them
13. Know how they are used in the lab to make esters