Organic Chem 1 Quiz - Addition

This is the first of my free Organic Chemistry 1 and 2 quizzes helping you to practice predicting major organic products of typical Organic Chemistry 1 addition reactions to alkenes and alkenes. Here are the addition reactions (and brief reaction overview) covered in this quiz:

(1) Hydrohalogenation: Addition of HX, where X = F, Cl, Br, or I. Follows Markovnikov's Rule: C in double or triple bond with the most Hs gets the H from HX, other C gets X. In terminal alkynes, i. e., triple bond starts at carbon 1, with 2 eq. of HX, 2Hs go to C with most Hs and 2Xs go to the other C.

(2) Halogenation: Addition of X2, where X = Cl or Br only)

(3) Hypohalous Acid Addition of Halohydrin Formation: Overall addition of "HOX", a Hypohalous Acid, where X = Cl, Br, or I. Note: I (iodine) successfully adds to alkenes with OH, but not as two I atoms. To match textbook coverage, this is reaction is restricted to alkene addition in the quiz.

(4) Acid-Catalyzed Hydration: Addition of H2O with acid catalyst, follows Markovnikov's Rule: C in double or triple bond with the most Hs gets the H from H2O, other C gets OH.

(5) Hydroboration-Oxidation: Anti-Markovnikov (C with least Hs gets the H), syn (same side) addition of H and OH to alkenes, In terminal alkynes, i. e., triple bond starts at carbon 1, 2Hs go to C with least Hs and =O goes to the other C in alkynes.

(6) Epoxidation: Adding O to C=C to make an epoxide, i. e., a three-membered ring with an O atom and two Cs.

(7) Syn-1,2-Dihydroxylation: Adding one OH to each C in an alkene, and both OHs are on the same side (syn).

(8) Ozonolysis: Cleaving C=C into two C=O groups, cleaving a terminal alkyne into a carboxylic acid and CO2, and cleaving an internal alkyne into two carboxylic acids.

(9) Catalytic Hydrogenation: Syn (same side) addition of H2 to C=C with H2 and Pd/C. Both alkenes and alkynes become alkanes.

(10) Syn addition of H2 to Alkynes to Make Cis-Alkenes: H2, Lindlar, doesn't react with alkenes.

(11) Anti-Addition of "H2" to Alkynes to Make Trans-Alkenes: Na, NH3 (liquid), -33oC. doesn't react with alkenes except benzene (usually this point is ignored in textbooks). No actually H2 used, just electrons from Na and protons from NH3.

(12) Deprotonation of Terminal Alkynes and Subsequent Alkylation: A terminal alkyne (triple bond starts at carbon 1) has a proton acidic enough to react with the strong base NaNH2 (sodium amide) to make an alkyne anion and NH3. Alkyne anion can subsequently react by SN2 with methyl and primary alkyl halides and sulfonates to make a C-C bond, useful in syntheses. Secondary and tertiary alkyl halides and sulfonates will mostly react with alkyne anions by E2, forming alkenes.