Mid-Term Exam (Organic Chemistry, AMIE261-00, Fall 2019)

October 21, 2019, 03:00 pm – 04:15 pm

Name: Prof. Jae Woong Jung
ID number:

Select True (T) or False (F) for each statement. (5 points each)
• For the structure of ethyelene, H atoms form σ bonds with four sp3 orbitals. ( F )
• The organic acids may lose a proton from C–H from a carbon atom next to a C=O double bond. ( F )
• Isomers that differ in how their atoms are arranged in chains are called constitutional isomers. ( T )
• Cycloalkanes are more flexible than open-chain alkanes. ( F )
• Chair conformations readily interconvert, resulting in the exchange of axial and equatorial positions by a ring-flip,
and thus two conformations of monosubstituted cyclohexane are equally stable. ( F )
• Aryl halides and vinylic halides do not react in Fridel-Crafts alkylation reaction because their carbocations are
very unstable to form. ( T )
• For the meta-directors in electrophilic aromatic substitution, Ortho and para intermediates destabilized because
inductive and resonance effects reinforce each other. ( T )
• Resonance forms differ only in the placement of their π or nonbonding electrons. ( T )

1. Give IUPAC names for the following molecules (5 points each)

(a) (b) (c) (d)

2. Predict the major organic product(s) in the reaction below. Suggest the exact reason for each product(s). (5 points each)
(a) (b) (c)
Br2, FeBr3 HBr

3. Determine the configuration of the carbon atom labeled with an arrow for following molecules. (5 points each)
(a) (b)

4. Determine the pair of molecules below as enantiomers, diastereomers, or identical. (5 points each)
(a) (b)

5. Draw the major product of the following reaction. (5 points)