Fill in the blank with the appropriate vocabulary word. If two or more words are
given, circle the correct one. (30 pts)
A) Radical bromination has a late / early transition state, is faster / slower and endothermic /
exothermic than radical fluorination.
B) If there are more than one stereocenters in a molecule, the molecule as a whole is sometimes /
always / never chiral. If there is only one stereocenter in a molecule, the molecule as a whole is
sometimes / always / never chiral.
C) In electrophilic addition reactions, the alkene acts as a(n) electrophile / nucleophile,
D) In free radical addition of H-X to alkene HCI / HBr / HI is the only one that works and the product
follows Markovnikov / Anti-Markovnikov rule.
E) KMnO4 reacts with alkene to give syn diols when diluted and cold / concentrated and hot. It
gives oxidative cleavage products when diluted and cold / concentrated and hot.
F) In the indirect hydration of alkenes with oxymercuration-demercuration, the reaction proceeds
through Anti-Markovnikov / Markovnikov with syn / anti addition of H and OH.
G) Electrophiles are always / sometimes / never Lewis bases while Nucleophiles are always /
sometimes / never Lewis acids.
H) In SN2 reactions, the nucleophile attacks the substrate from the front / back / either side, and
the product will have retention / inversion / racemization of stereocenter.
I) The overlap of neighboring orbitals to stablize radicals and carbocations is called
This makes 3°/2°/1° radicals the most stable radicals.
J) On IR spectrum, the region between 2750 and 3650 cm-¹ corresponds to X-H / double bond /
K) In E1 reactions, the hydrogen and the leaving group must be syn / anti / either for the reaction to
effect is a scenario where halogens near an alcohol withdraws electron
density from the conjugate base. This makes the acid stronger / weaker because of the
halogens stablize / destabilize the conjugate base.
M) Jones reagent oxidizes secondary alcohols to aldehyde / ketone / carboxylic acid.
N) When primary alcohols are reacted with nucleophilic acids such as HI and HBr, they will undergo
SN1 / SN2 / E1 / E2 reaction.
O) Nucleophiles attack the least / more substituted side of epoxides when the reaction is run under
P) During an oxidative cleavage with hot and conc. KMnO4, the alkene carbon if di-substituted
, if mono-substituted becomes a(n)
; and if non-
substituted becomes a(n)
Q) Nucleophilicty increases / decreases / remains the same and the acidity of a molecule
increases / decreases / remains the same as we go from left to right on the periodic table and.
PART II. Nomenclature: (25 pts)
Give the IUPAC name for the following compounds or draw the correct structure for the
given names. Use absolute stereochemistry (R, S, E, Z) where appropriate.
Part III: Short answers.
i) Give the hybridization of the indicated atoms as SP, SP2, SP³ or unhybridized. (10 pts)
ii) What is the shape (geometry) at the indicated carbon above? (3 pts)
iii) How many chiral carbons are present in the above molecule? (1 pt)
electron movement arrows. Circle the most stable resonance structure. (7 pts)
compounds may be used more than once, and some may not be used at all. (11 pts)
vi) Convert the following condensed formulas into their bond line structures. (5 pts)
Part III. Short answers continued:
vii) For each of the given pairs of molecules, circle the one that is MORE STABLE. If they have
equal stability write SAME. Give a brief explanation describing the chemical principle that
makes it more stable. (10 pts)
viii) Identify the relationship between the following molecules. Possibilities are Same Meso (M),
Constiutional Isomers (C), Enantiomers (E), Diastereomers (D) and Identical Chiral (l). (8 pts)
Short Answers continued
ix) For each of the given pairs or substrates circle the molecule which would result in a faster SN2
reaction if all other factors were the same. In the space provided, state why that molecule
would have a faster reaction. (i.e. What fundamental principle causes faster reaction) (12 pts)
a) NH3 Vs PH3 as nucleophile
b) H2O Vs CH3COCH3 as solvent
c) F-Vs Br° in aprotic solvent
x) Look at the given molecules and answer the following questions (8 pts)
a) How many different chemical environments (number of peaks) would you expect to see in the
1HNMR spectra for each molecule?
b) Predict how many sub peaks would be seen in the 1HNMR spectrum for the indicated
hydrogen due to spin-spin splitting?
stereochemistry if applicable. Assume a
NaN3 , HMPA
1) mCPBA, CH2CI2
2) CH3OH, H+
2) t-BuOK, t-BuOH
1) H2. Pd
2) Br2, Au
Part IV. Reactions continued.
Draw the structure of the major organic product(s) formed in t
otherwise. If no reaction occurs, write NR. (21 pts)
1) Hg(OAc)2 H2O
2) / S
Part V: Mechanism.
stucture Include complete, all of all of write mechanism all non-zero for charges, the following and reaction. draw
.. N=N=CH2, Au or heat
Show how you would efficiently synthesize the final molecule (right) from the
provided starting material (left). Provide the reagents for each reaction step and draw
all resulting products for each step. Note: No arrow pushing mechanism is required to
answer this question. (10 Pts)
Part VII: Spectroscopy,
Using the following spectra, draw a possible structure for C6H12C in the given box. (10 Pts)
Degree of Unsaturation =
IR: 3300 strong/broad, 3100 strong/sharp and 1600 medium/sharp.
1H, br. S
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