Summary: Organic Chemistry.

I. Nomenclature.

1. Know the IUPAC systematic organic nomenclature method:

prefix - root - suffix.

2. Know the root names for from one to ten carbons.

3. Know the use of prefixes and locants for the designation of:

a. rings

b. branches

c. halogens

4. Know the use of suffixes (including priority rules), prefixes (when necessary) and locants for the naming of:

a. C,C double bonds (including cis/trans)

b. C,C triple bonds

c. C-OH groups

d. C=O groups in aldehydes, ketones and acids.

5. Know the meaning of 1, 2 and 3 when applied to carbon atoms.

Example Questions.

1. Sketch line structures for the following organic molecules:

a. 4-Ethyl-2,3,5-trimethyloctane

b. trans-But-2-ene

c. 3-Methylcyclopentan-1-ol.

d. 2-Chloro-3-isopropylheptanal

e. 2-Hydroxy-5-methyl-4-oxodecanoic acid

2. Name the following organic molecules according to the IUPAC method:

II. Reactions.

Be able to give examples of, predict reactants, reagents, and/or products of the following organic reactions.

Functional Group Reagent Product
Haloalkane (not F) OH- Alkanol
Haloalkane R-CC- Alkyne
Haloalkane LiAlH4 (H-) Alkane
Alkene Br2, I2, Cl2 (1,2)-Dihaloalkane
Alkene HCl, HBr, HI Haloalkane
Alkene KMnO4 (cold) (cis)-Alkane-(1,2)-diol
Alkene H2 / Pt (catalyst) Alkane
Alkene ROOR(radical) Polyalkene
Alkyne Br2, I2, Cl2 (1,1,2,2)-Terahaloalkane
Alkyne HCl, HBr, HI (1,1)-Dihaloalkane
Alkyne H2 / Pt (catalyst) Alkane
Alkyne H2 / Pd, BaSO4 (cis)-Alkene
Alkanol KMnO4 1: Alkanoic acid

2: Alkanone

3: no reaction

Alkanol ZnCl2 / HCl(aq)

or HBr or HI

Alkanol Alkanoic acid / H+ Ester (or polyester)
Alkanal Tollen's (Ag mirror) Alkanoic acid
Alkanal 2,4-DNP 2,4-DNP deriv.
Alkanal LiAlH4 (H-) Alkanol (1)
Alkanal R-CC- Alk(-2-)yn(-1-)ol
Alkanone 2,4-DNP 2,4-DNP deriv
Alkanaone LiAlH4 (H-) Alkanol (2)
Alkanone R-CC- Alk(-2-)yn(-1-)ol
Alkanoic acid Alkanol Ester (or polyester)

Example Question Fill in the appropriate box in the following reactions: