Download Exam Paper - Organic Chemistry II | CHM 223 and more Exams Organic Chemistry in PDF only on Docsity! 1. MATCH a structure or term from the following list with each description below. Place the letter of the structure or term in the blank to the left of the description. (3pts. Each) a. benzyne b. +NO2 c. R3C+ d. electron-donating e. +NO f. Meisenheimer complex g. R - C O+ h. electron-withdrawing __________ The reactive electrophile in Friedel-Crafts acylation reactions. __________ The electrophile in aromatic nitration. __________ Groups which activate aromatic rings towards electrophilic substitution. __________ Groups which activate aromatic rings towards nucleophilic substitution. __________ Intermediate in the elimination-addition mechanism of nucleophilic aromatic substitution. 2. Draw a structures corresponding to the following IUPAC names. (1pt. each) 3-methyl-2-buten-1-ol diethyl ether 3. Rank the compounds in each group below according to their reactivity toward electrophilic aromatic substitution (most reactive 1 ; least reactive 3 ). Place the number corresponding to the compounds’ relative reactivity in the blank below the compound. (3pts.) 4. Consider the reaction below to answer the following question. Draw resonance structures for the intermediate carbocation that explain the directing effect of the -Br.(8pts.) CH2FCH3F Refer to the data below to answer the following questions. 8. The weakest acid in the table is: (3pts.) 9. A highly useful and general method for the synthesis of alcohols is the addition of Grignard reagents to carbonyl compounds. Show what Grignard reagent and what carbonyl compound you would start with to prepare the alcohol below. (6pts.) 10. 17. 10. Propose structure(s) for the starting material(s), reagent(s), or major organic product(s) of the following reactions or sequences of reactions. Show all relevant stereochemistry. (3pts. each, 33pts. total) 11. CH)CH3,
NBS
(PhCO3)2, CCly
oO
Il
cHo CH,CCI
3 AIC,
Ol
H,0, acetone
Ul
1. NaBLL,, ethanol
Sa
2. H,0'
oO
CH;
KMn0O, Bp
#30! Kelirs
