CHM 2200 Exam 3 - Fall 2014: Multiple Choice Questions and Organic Reactions - Prof. Tammy, Exams of Organic Chemistry

Download CHM 2200 Exam 3 - Fall 2014: Multiple Choice Questions and Organic Reactions - Prof. Tammy and more Exams Organic Chemistry in PDF only on Docsity! Exam 3 – CHM 2200 – Fall 2014 (Davidson) Name: UF ID: 1. (3 points) ***Important reminder*** The final exam for this course has been rescheduled for Saturday, December 13 at 10:00am in Leigh 309. Check the box at the end of this question to acknowledge that you know about the schedule change and to receive your points.  2. (14 points) Circle True or False for the following statements. a) True or False: β-Elimination reactions favor formation of the less highly substituted alkene product. b) True or False: An –OH group is a poor leaving group in substitution reactions. c) True or False: Ethers are generally more reactive than alcohols, which is why they are poor solvents. d) True or False: PCC will oxidize a secondary alcohol to a ketone. e) True or False: The mechanism of electrophilic aromatic substitution involves a three step process: generation of the electrophile, addition of the electrophile to the ring, and removal of a proton to regenerate the aromatic ring. f) True or False: If a benzene ring has both an activator and a deactivator group, the deactivator will direct the placement of the next group to be added to the ring. g) True or False: An amino group (–NH2) can be directly added to a benzene ring through an electrophilic aromatic substitution reaction. 3. (6 points) Circle the compounds below that are aromatic. O S N O H 4. a) (3 points) Which of the structures shown below is the stronger acid? Briefly explain. OHOH vs. b) (3 points) Which of the structures shown below is the stronger base? Briefly explain. vs.NH2CH3O NH2O2N c) (4 points) Rank the following compounds in order of increasing reactivity in electrophilic aromatic substitution (1=slowest, 4=fastest). NO2CH3 OCH3 5. (9 points) Draw the structures of the major organic products from the reactions shown below. a) H2CrO4 b) CH3 O CH3 HNO3 H2SO4 c) NO2 H2, Ni 6. (8 points) When the alcohol shown below is treated with HBr, an alkyl halide product forms. OH BrHBr a) Does this reaction most likely occur through an SN1 or SN2 mechanism? _____________ b) Draw the structure of the intermediate that forms right after the loss of the leaving group. c) Based on the structure of the product, it should be clear that a rearrangement has occurred. Briefly explain why this happened.