Draw the structure of the following three isomeric acid chlorides with chemical formula C6H₂CIO. • Use the wedge/hash bond tools to indicate stereochemistry where it exists. • Consider E/Z stereochemistry of alkenes. • In cases where there is more than one answer, just give one. Acid chloride #1: cis-3-methylcyclobutanecarbonyl chloride

2. The molecules shown below are four terpineol isomers. They are isolated from plants and have distinct aromas. For example, a -terpineol is a common perfume ingredient and smells similar to lilacs. Hol H-O- a-terpineol B-terpineol Y-terpineol 4-terpineol A) Draw a structural isomer of terpineol that meet the following criteria. You should draw one unique structure for each set. You must draw each molecule twice, once as a skeletal structure and once as a complete Lewis structure showing all atoms, bonds, and lone pairs of electrons. i. Does not have a ring. ii. Has an E alkene. iii. Has a secondary alcohol. iv. Does not contain an alcohol. B) Draw a complete Lewis structure of a-terpineol showing all bonds, atoms and lone pairs of electrons.

Provide an IUPAC name for each of the compounds shown. (Specify (E)/(Z) stereochemistry, if relevant, for straight chain alkenes only. Pay attention to commas, dashes, etc.) CH3 CH3 ČH3 Br, CH3 C=C H H2C-CH2

For the molecule given, prioritize each substituent on the stereogenic carbon, and assign absolute stereochemistry.