Test 5 (Lecture 5 / Module 5): 5 points
1. For each reaction below, look at the reagents and conditions (above and below the a
ow) and draw
the final product. Determine if it proceed via: SN1, SN2, or neither (no reaction) (2 points):
(a) (0.4 points):
Answer:
(b) (0.4 points):
Answer:
(c) (0.4 points):
Answer:
(d) (0.4 points):
Answer:
(e) (0.4 points):
Answer:
2. (a) Circle ONLY GOOD LEAVING GROUPS which can be replaced in SN1 or SN2 reactions (0.5 points):
(b) Which one is THE BEST LEAVING GROUP (0.5 points):
Hint: use the chart on page 151 (Chapter 9.4):
Answer:
3. Identify if the following (SOLVENT, SUBSTRATE, NUCLEOPHILE, LEAVING GROUP) are best for SN1 or
SN2 reactions or BOTH (2 points):
SN1 SN2
SECONDARY (SUBSTRATE)
‒
(example)
YES
(example)
TOSYLATE (OTs)
GOOD (LEAVING GROUP)
YES
(example)
YES
(example)
(NUCLEOPHILE)
(SUBSTRATE)
(NUCLEOPHILE)
(NUCLEOPHILE)
(SUBSTRATE)
TRIFLATE (OTf)
(LEAVING GROUP)
(SUBSTRATE)
WATER (H2O)
(SOLVENT)
DMSO
(SOLVENT)
(SOLVENT)
MIDTERM (Lecture 1 – 5 / Module 1 – 5): 20 points
1. Show a mechanism for the acid-base reaction and determine the position of equili
ium. (5 points):
(a) (2.5 points)
Answer:
(b) (2.5 points):
Answer:
2. Draw the structures of the following compounds. (5 points):
(a) 2-chloro-3-ethyl-2,4-difluoro-4-methylnonane (1 point):
(b) 4-ethyl-2,4-dimethylcyclohexa-2,5-dien-1-one (1 point):
(c) (Z)-2-
omo-1-chloro-1-fluoroprop-1-ene (1 point):
(d) (1R,3R)-3-methylcyclohexan-1-ol (1 point):
(e) 3-amino-5-
omo-4-cyclopropyl-2-fluoroheptan-1-al (1 point):
3. (a) Identify the type of hy
idization (sp, sp2, sp3) of each atom (C atoms O atoms and N atoms) of the
following compound (2 points):
sp = BLUE circle or sphere
sp2 = GREEN circle or sphere
sp3 = RED circle or sphere
(b) Identify the type of hy
idization (sp, sp2, sp3) ONLY of N (NITROGEN) atoms of the following
compound (2 points):
4. Draw a chair conformation, a flipped chair conformation and identify the most stable chair
conformation and explain why (6 points):
(a)
(b)
(c)
(d)
(e)
(f)
BONUS QUESTIONS:
1. For the compounds below (a) draw both Conjugate Base 1 and Conjugate Base 2. Determine which of
the two protons is more acidic using the ARIO rule and explain your reasoning - if the reason is R
(number of Resonance Structures) please draw all the resonance structures. Make sure you keep track
of all formal charges and lone pairs (1 point):
Conjugate Base 1:
Resonance:
Conjugate Base 2:
Resonance:
Answer:
2. Answer the questions and fill each box below (total 2 points = 0.1 points x 20 boxes):
Find all of CHIRAL
centers
“Circle or label
them if they exist”
Is it a MESO
form?
YES/NO
Name each
CHIRAL center
(R or S if they
exist)
Draw the
ENANTIOMER
“if it exists”
Remember: meso
forms do not have
enantiomers
Draw a
DIASTEREOMER
3. Draw Newman projection for the compound below (2 points):
Hint: You have to draw two connected Newman projections.
Name: (1S,2R,5S)-2-isopropyl-5-methylcyclohexan-1-ol
(A) Newman 1 (1 points):
(B) Newman 2 (1 points):