23 Questions in Exam 3 | Organic Chemistry II | CHEM 3153, Exams of Organic Chemistry

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f CHEM 3153: Exam 3 NOTE: Bubble in Your Name (Last, space, First) \ tt a Oe Wy Bubble in Special Code 000031 1. Acetyl chloride undergoes nucleophilic substitution at a faster rate than methyl acetate because: £ A) the ester ismore-sterically-hindered than the acid chloride. -_ -B) the aeid_chloride is more sterically hindered than the ester: C) the methoxide is a better leaving group than chloride. D) ester hydrolyze faster than acid chlorides, af © chloride is a better leaving group than methoxide. oe 2. Which of the following compounds would yield acetic acid when hydrolyzed under heat? Ou Sd. oe oh” oh H3C~ ~O~ “CH, H3C—C=N HC~ ~cl H,;C~ “OCH, \l Wn ) | 1 Iv) A)I s F) TandIV B) Il G) Il and IV Cc) H) I, TI and Wi D) IV 1) 1, Wand Iv E) Tand Il @ I, 11, 1 and IV 3. Which of the following conditions will drive the equilibrium of the Fischer esterification towards ester formation? ‘ nt < oO HCI 9 we + CHO === + HO Pie age A) addition of water E) both A and B @) removal of water as it formed both B and D Oo addition of an inorganic acid as a catalyst ) A, B,and D ® addition of alcohol H) A,B,C, and D 4. What is the IUPAC name for the following compound? a 9 ° a Oke re AAA ™ ae sent eget H OCH,CH, cil Pe A) 1-ethyl-5-oxopentanoate D) 6-oxa-1 5-dioxooctane B) 6-oxa-5-oxooctanal E) |-ethoxypentanedial C) 5-ethoxy-5-oxopentanal @® ethyl 5-oxopentanoate 5. List the following carbonyl compounds in order of decreasing reactivity towards nucleophiles: = \ ester, acid chloride, ketopie, amide, midepyie A) ester > acid chloride > ketone > amide > aldehyde (B) acid chloride > aldehyde > ketone > ester > amide pcre calor! amide > ketone > ester > aldehyde > acid chloride D) acid chloride > ester > aldehyde > ketone > amide E) amide > ester > acid chloride > ketone > aldehyde > ALO > EFT» > tee