E test Module 7 Organic chem 1 (Chem-40010) University of California (San Diego), Exams of Organic Chemistry

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Question 1 Please predict the products for each of the following reactions, Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Hint: In this case you must choose the best answer to demonstrate the stereochemistry of H2 addition. Fa 2 g g & 6 3 ia be} CamScanner oo { | ae Question 2 l Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). Ifa mixture of enantiomers is formed, please draw all the enantiomers. be} CamScanner | Question 4 L Please predict the products for each of the following reactions, Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). if a mixture of enantiomers is formed, please draw all the enantiomers. be} CamScanner Question 6 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. be} CamScanner Question 10 Please predict the products for each of the following reactions. ° Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. be} CamScanner Question 11 Please predict the products for each of the following reactions, Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. i \ | S \ 2 | | 2 g z g : a faa ae Question 13 Please predict the products for each of the following reactions. 3 Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereocher If a mixture of enantiomers is formed, please draw all the enantiomers. \ y | | mistry (syn- vs anti- or both). Question 14 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. | Question 16 | Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. be} CamScanner | Question 17 Re ee By IF IS 0 eee Ol oo POND Eo Deke oe es MOR ees SREP | | Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or bot If a mixture of enantiomers is formed, please draw all the enantiomers. be} CamScanner Question 19 Please predict the products for each of the following reactions. Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. be} CamScanner Question 20 Please predict the products for each of the following reactions. . Clearly show the regiochemistry (Markovnikov vs anti-Markovnikov) and stereochemistry (syn- vs anti- or both). If a mixture of enantiomers is formed, please draw all the enantiomers. Reee saa : WA ) “hte neh @ secondary carbocation Mechanism C: proton transfer me ON H3C eh dilute H-Cl: secondary carbocation Mechanism D: a methyl migration (rearrangement) spree attack abies attack 2Cl: methyl * Hs tertiary disassosiation carbocation proton cy disassosiation dilute H-CI: ®©® 0 O on > oO o 0 66-32 secondary carbocation tertiary carbocation fucleophilic attack Vat >) secondary aN carbanion | © >) proton transfer H Question 22 - i i alt iran | Select correct and most relevant mechanism for each of the following reaction. Hint: Review Chapter 11.4. . Bi dilute H8r Mechanism A: nucleophilic attack reas transfer OQ H © Z H UGH, H CH } 6 \A H) proton ferrin Br ne H-Br? Br pane transfer ) se * ‘0 tertiary ‘Bri carbocation Mechanism B: hydrogen migration — transfer _‘(fearrangement) nucleophilic attack a ) H® at CH. Gott dilute H-Br: ae 3° ol VY secondary nf tertiary carbocation a carbocation = Cc: aw i nucleophilic -O 2 « it, a A ’ :Br: “Br. Me) la ‘Bh i ) CH; Pea C O ccssde : bs tyl ll dilute H-Br? attack ie tl ed proton transfer Th elimination primary La carbanion *Br: proton proton transfer, (y disassosiation ° B na ‘3 dilute H-Brt a -e@ i Hoh : be} CamScanner