2. a-pinene is one of the constituents of turpentine. It can be found in many essential oils, such as that of rosemary, eucalyptus oil, and orange peels. Another common place to find a-pinene is cannabis plants. The concentration in marijuana is believed to contribute significantly to the side effects felt (such as memory impairment). H+ Propose a facile synthesis route for one of the diastereomers HBr Br2 CCl4 Br2 H₂O NaOEt EtOH LOH O3, -78°C (CH3)2S H2SO4 A

gas, Cl¬CH2CH2¬S¬CH2CH2¬Cl, was used as a poisonous chemical agentin World War I. Mustard gas is much more toxic than a typical primary alkyl chloride. Itstoxicity stems from its ability to alkylate amino groups on important metabolic enzymes,rendering the enzymes inactive.(a) Propose a mechanism to explain why mustard gas is an exceptionally potent alkylatingagent.(b) Bleach (sodium hypochlorite, NaOCl, a strong oxidizing agent) neutralizes and inactivates mustard gas. Bleach is also effective on organic stains because it oxidizes coloredcompounds to colorless compounds. Propose products that might be formed by thereaction of mustard gas with bleach.

Tunicates are marine animals that are called "sea squirts" because when they are taken out of water, they tend to contract and expel seawater. Lepadiformine is a cytotoxic agent (toxic to cells) isolated from a marine tunicate. During a recent synthesis of lepadiformine, the investigators observed the formation of an interesting by-product (3) while treating diol 1 with a reagent similar in function to PBr3 (J. Org. Chem. 2012, 77, 3390–3400):

select the most appropriate reagent(s) to effect the change. K2Cr2O7, H+ H2, Pd 1. Disiamylborane,  2. HO–, H2O, H2O2 NaOCl H2SO4, HgSO4