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| Question 1 * 0.2 | Draw Zaitsev and Hofmann products that are expected when each of the following compounds is treated with a strong base to give an E2 ELIMINATION product. Hint: Some compounds cannot produce both elimination products because they do not have two beta-hydrogen atoms: in these cases only ONE product will be possible. In cases when neither elimination products are possible, there will be NO REACTION. 4 2 Br a he} | 4 pe |42 Zaitsev Hofmann only ONE product is possible oc 6 of WT} 4 only ONE: product is possible Hofmann Zaitsev 7 Oo > (@) o Question 2 Draw Zaitsev and Hofmann products that are expected when each of the following compounds is treated with a strong base to give an E2 ELIMIN product. Hint: Some compounds cannot produce both elimination products because they do not have two beta-hydrogen atoms: in these cases only ONE product wi possible. In cases when neither elimination products are possible, there will be NO REACTION. Leg cl A pee SU B. NO products are possible (NO REACTION) Zaitsev Hofmann only ONE product is possible Hofmann Zaitsev 0.2 | Draw Zaitsev and Hofmann products that are expected when each of the following compounds is treated with a strong base to give an E2 ELIMINATION product. Hint: Some compounds cannot produce both elimination products because they do not have two beta-hydrogen atoms: in these cases only ONE product will be possible. In cases when neither elimination products are possible, there will be NO REACTION. OX — ? A NO products are possible. B | Cp o> (NO REACTION) Zaitsev 1 Zaitsev 2 Zaitsev Hofmann only ONE product is possible Question 5 “ 0.2 pts Draw Zaitsev and Hofmann products that are expected when each of the following compounds is treated with a strong base to give an E2 ELIMINATION product. Hint: Some compounds cannot produce both elimination products because they do not have two beta-hydrogen atoms: in these cases only ONE product will be possible. In cases when neither elimination products are possible, there will be NO REACTION. 1 NO products are possible : dy A (NO REACTION) B only ONE product is possible nn Zaitsev Hofmann Zaitsev Hofmann OA @B oc | lon) Question 7 : i Draw major E2 ELIMINATION product. Hint: Review Chapter 10.3, the elimination can only occur if the leaving group (Cl, Br, |, OTs, etc) and beta-hydrogen atom (H) are in anti-pe: Red bond = the location of a double bond in the final product and the direction of a Newman projection: cl : a A B Cc D Zee a a NN BN Et OA OB €c ° od luck! Question 8 Draw the appropriate Newman projection which leads to the major E2 ELIMINATION product. Hint: Review Chapter 10.3, the elimination can only occur if the leaving group (CI, Br, I, OTs, etc) and beta-hydrogen atom (H) are in anti-periplanar conformation. Red bond = the location of a double bond in the final product and the direction of a Newman projection: Br : AK ————_— anti-periplanar conformation maj ! el A B c D | H3C._CH; H3C._CH; H3C.__CH; | fac H H3C H H Bp H;C CH; ‘CH; Et (Be CH3 Newman Newman Newman OA OB .e) @® o 0 Question 10 0.2 Draw the appropriate Newman projection which leads to the major E2 ELIMINATION product. Hint 1: Review Chapter 10.3, the elimination can only occur if the leaving group (Cl, Br, |, OTs, etc) and beta-hydrogen atom (H) are in anti-periplanar conformatio Red bond = the location of a double bond in the final product and the direction of a Newman projection. Hint 2: D is a deuterium atom (D is an isotope of H atom and has very similar chemical properties). You have to decide if beta-H or beta-D atom will be eliminated to form the major product. You will have to dra iw two Newman projections and decide which one is the most stable (energetically). CH; H——-D anti-periplanar conformation H-7—5r major Hae preellactl CH; A B c D H CH; Et H IBY H en) H By D li) CH3 H3;C D H CH; CH; ol Hy CH; CH3 major Newman major Newman major Newman major Newman OA OB @c oD Question 11 Draw major E2 ELIMINATION product. Hint 1: Review Chapter 10.3, the elimination can only occur if the leaving group (Cl, Br, |, OTs, etc) and beta-hydrogen atom (H) are in anti-periplanar c Red bond = the location of a double bond in the final product and the direction of a Newman projection. Hint 2: D is a deuterium atom (D is an isotope of H atom and has very similar chemical properties). You have to decide if beta-H or beta-D atomy eliminated to form the major product. You will have to draw two Newman projections and decide which one is the most stable (energetically). CH; of 9 | H-—Br | — CHs | A B Cc D D H H H H . Hye SY Ho S Os ioe wyo7NH | CH3 H D CH; | os | @B | oc Draw major E2 ELIMINATION product. Question 13 mea TE mile ie iA Hint: Review Chapter 10.3, the elimination can only occur if the leaving group (Cl, Br, |, OTs, etc) and beta-hydrogen atom (H) are in anti-periplanar conformati antr-peri conformation Red bond = the location of a double bond in the final product and the direction of a Newman projection: A — ? 1 | Br A B -¢ 5 _ NN : S OA OB , ; @c OD Question 14 Draw the appropriate Newman projection which leads to the major E2 ELIMINATION product. Hint: Review Chapter 10.3, the elimination can only.occur if the leaving group (CI, Br, |, OTs, etc) and beta-hydrogen atom (H) are in anti-periplanar conformatio, Red bond = the location of a double bond in the final product and the direction of a Newman projection: Ww 3 —— anti-periplanar conformation _e—_— nayor f fol) A B c D CHy CH; Et CH; H CH; CH; » B HC H3C HC H3C H Et Et j Et Et Et Et H Newman Newman Newman Newman OA @®B oc OD (D> Question 16 Identify the Major and ALL Minor product(s) that are expected for each of the following reactions. Hint 1: Combination of E1 / E2 or SN1 / SN2 or both. Hint 2: Use Flow Charts on page 167 (Chapter 10.9). NaSH o acd A Ay B Ag i pe A SH c Aon : SH D NO products are possible _(NO REACTION) OA OB @c OD + Question 17 Identify the Major and ALL Minor product(s) that are expected for each of the following reactions. Hint 1: Combination of E1 / E2 or SN1/ SN2 or both. Hint 2: Use Flow Charts on page 167 (Chapter 10.9). AX NaOH 9 OMs — C B NO products are possible (NO REACTION) Question 19 Identify the Major and ALL Minor product(s) that are expected for each of the following reactions. Hint 1: Combination of E1 / E2 or SN1 / SN2 or both. Hint 2: Use Flow Charts on page 167 (Chapter 10.9). NaOEt o cl —* ; a A DA + AK major minor B Zz + Ak + 1X major | minor minor Cc ANZ. a * OEt major minor @A OB oc oD 0.2 . [ Question 20 Identify the Major and ALL Minor product(s) that are expected for each of the following reactions. Hint 1: Combination of E1 / E2 or SN1 / SN2 or both. Hint 2: Use Flow Charts on page 167 (Chapter 10.9). HOH o I major minor SY minor major o* BG, major minor 
