CHEM 31.1 ORGANIC CHEMISTRY LABORATORY Problem Set Organic Nomenclature Answer the questions on a clean sheet of paper.

Use BLACK or BLUE INK only. Pencil marks will not be checked. Write/Draw clearly and legibly. I. Draw the following compounds (2pts @) a. p-ethynylphenol b. 7,5-diethyl-3,4-dimethyl-6,8-dipropyltridecane c. tert-butylamine d. isobutyl mercaptan e. o-aminobenzoyl chloride

f. dimethoxymethane g. 3,4,5-triiodoanisole h. trifluoroacetic acid i. cyclopentyl alcohol j. m-crotylstyrene

II. Name the following compounds using the IUPAC format (2pts @) CH3 a. b.
S O H3C CH3
O
+

SH CH3 Cl Cl CH3

CH3 CH3
-

CH3 O CH3
HO

OH OH NH2

N CH3

+ -

c.

d.

OH

e.

III. Draw the compounds in Column A and match them with a description in Column B. (3pts @) COLUMN A COLUMN B N-ethyl-3-fluoro-N-methylbenzamide A. Has a positively-charged nitrogen 6-bromo-4-cyclobutyl-3-hydroxy-5-nitro-2-octanone B. Secondary amine 3-chloro-2-ethynyl-5-methoxycyclohexanethione C. Tertiary halide 2-amino-3-chloro-N-(1-methylethyl)cyclopentanone D. Meta substituted (1-bromo-1-methylpropyl)cyclobuta-1,3-diene E. Has an sp carbon IV. Draw the structures and check if the name follows IUPAC format. If it does, write Oh Yeah! and if it does not follow the IUPAC format then write the correct name in correct IUPAC format. (4pts @) 1. 6-butyl-4-chloro-3-cyclohexylheptanal 2. 5-hydroxycyclopenta-1,3-dien-1,2-amine 3. 2,5-dichlorocyclohexa-2,5-dien-1,4-dione 4. 5,11-dibutyl-7-(methylsulfanyl)trideca-3,8-dien-2,10-dione 5. 1,3,5-trinitro-2,6-biphenylbenzene

V. Write Yes, it is! if the statement is TRUE and, No, it is not if the statement is FALSE. (1pt @) 1. The C-N bond in ethylamine is longer than the C-N bond in acetamide. 2. There is no sp3 carbon found in the compound 1,3-cyclopentadiene. 3. The C=O bond in formamide has the same bond energy as the C=O bond in formaldehyde. 4. Cyclic esters are called lactones while oxiranes are three-membered cyclic ethers. 5. The IHD of styrene is 5. 6. The compound 2-propanol is a secondary alcohol. 7. The C-C bond order in ethene is greater than the C-C bond order in ethyne. 8. The condensed formula for 2,2-dimethylheptane is (CH3)3C(CH2)4CH3. 9. The boiling point of neopentane is higher than that of n-pentane. 10. Octadecanoic acid is also called stearic acid. VI. Complete the table. (1pt @) Formula Characteristic C5H12O Tertiary alcohol C3H9N Secondary amine C5H10 All are secondary hydrogen atoms An enal that does not exhibit C4H6O resonance C4H8O Open-chain ether

IHD

Structure

IUPAC name

Common name