Ch#41c,#Organic#Chemistry# Quiz#1# Question 1 _____/12 points Question 2 _____/08 points Question 3 _____/16 points Question 4 _____/16 points Question 5 _____/16 points Question 6 _____/16 points Question 7 _____/16 points TOTAL _____/100 points Name (printed) Signature There are six pages (2–7) of questions in this exam. There is a periodic table on page 8. 1 of 8 April#23,#2014 (1) (3 points each, 12 points total) Please provide: (1) the ML aXb assignment (i.e., give a and b) ________ Cl PPh 3 (2) the formal oxidation state of the metal ________ CO (3) the dn electron count (i.e., give n) ________ Ir Ph 3P (4) the total electron count ________ (2) (4 points each, 8 points total) Please provide the product of the illustrated reactions. Ph I cat. Pd(PPh 3)4 cat. Cl PCy 3 Cl Ru CH2 PCy 3 2 of 8 (3) (16 points) Please provide the best stepwise mechanism for the illustrated transformation, including the name of each elementary step (e.g., ligand substitution, oxidative addition, reductive elimination, β-migratory insertion, β-elimination, α-migratory insertion, four-center reaction, or [2+2] reaction). Me H H CO O HCo(CO) 4 H Me H 3 of 8 (4) (4 points each, 16 points total) Please provide the product of the illustrated reactions. If no reaction is expected, write "NR". O Me H OMe O Me NaBH 4 NMe 2 O Me H Me O Me EtOH (solvent) EtOH (solvent) SOCl2 OH 4 of 8 (5) (16 points). An amide hydrolysis performed under basic conditions in labeled water was stopped before the reaction was complete. The "unreacted" amide contained mostly labeled oxygen in the carbonyl oxygen. Please provide the best explanation for this observation, including a mechanism for the formation of the labeled amide (with all arrow pushing). O Me HO NMe 2 (1 equivalent) H 2O O Me 5 of 8 + carboxylate NMe 2 (6) (16 points) A hemiaminal ether can be converted into a ketone upon treatment with aqueous acid. Please provide the best mechanism for this process, including all arrow-pushing O Me NMe Me H (1 equivalent) H 2O O HO Me a hemiaminal ether 6 of 8 Me NH 2Me (7) (16 points total) In the Negishi reaction illustrated below, in addition to the formation of the desired product (PhCD 2CD 3), some Ph–D (an undesired side product) was isolated at the end of the reaction, Please provide the best stepwise mechanism for the formation of Ph–D. Ph I BrZn CD2CD 3 cat. Pd(PPh 3)4 7 of 8 Ph CD2CD 3 Ph D 18 1 13 2 3 132.90 137..33 (223) (226) 8 of 8 14 15 16 17