Chem 112A Fall 2012 Homework A Based on lecture 8/23/12 1) Add hydrogen atoms to the structures found in the

the lecture notes, and write a molecular formula for each. 2) Identify as many functional groups as you can in the same set of molecules. 3) Additional molecules to practice (write molecular formulas and identify functional groups): tetrahydrofuran (a common laboratory solvent) Molecular Formula: C4H8O Functional group(s): ether

propargyl alcohol (a useful synthetic building block) Molecular Formula: C3H4O Functional group(s): alkyne, alcohol

leucine (the most common amino acid in proteins) Molecular Formula: C6H13NO2 Functional group(s): amine (protonated ammonium ion), carboxylic acid (deprotonated carboxylate ion)

geraniol (a natural insect repellant found in geraniums) Molecular Formula: C11H20O Functional group(s): alkenes, alcohol

Correction: the structure above was misdrawn. Geraniol is actually C10H18O, shown below: OH

ibuprofen (an analgesic) Molecular Formula: C13H18O2 Functional group(s): aromatic ring, carboxylic acid

vitamin c (required for collagen biosynthesis) Molecular Formula: C6H8O6 Functional group(s): alkene, alcohols, ester

ethyl acetate (a common laboratory solvent) Molecular Formula: C4H8O2 Functional group(s): ester
O O

ethyl cinnamate (an aroma component in cinnamon) Molecular Formula: C11H12O2 Functional group(s): alkene, aromatic ring, ester

vanillin (the principal aroma component of vanilla) Molecular Formula: C8H8O3 Functional group(s): phenol, ether, aldehyde

Periplanone B (the sex attractant of the female cockroach) Molecular Formula: C15H20O3 Functional group(s): alkenes, ethers, ketone

Captopril (a medication used to treat high blood pressure) Molecular Formula: C9H15NO3S Functional group(s): carboxylic acid, amide (note that the nitrogen is part of the amide, so it is not considered an amine)

quinine (anti-malarial compound found in tonic water) Molecular Formula: C20H24NO2 Functional group(s): ether, aromatic ring, alcohol, amine, alkene

methionine-tyrosine dipeptide (a component of many proteins) Molecular Formula: C14H20N2O4S Functional group(s): phenol, carboxylic acid, amide, amine

cyamemazine (antipsychotic used to treat symptoms of drug withdrawal) Molecular Formula: C19H21N3S Functional group(s): aniline, aromatic ring, amine, nitrile

erythromycin (an antibiotic) Molecular Formula: C37H67NO13 Functional group(s): ketone, alcohols, ester, ether, amine