5:08 Back CHE 2511_Tutorial S... CHE 2511 BASIC ORGANIC CHEMISTRY QUESTION ONE (a) The following reactions either proceed through an E2 or an SN2 mechanism. Give the major product of the following bimolecular reactions. (i) (ii) (iv) Jok (ii) E OTS (i) CI *OK* + CH₂-Br H₂C-CH₂ CI CH3 x (i) Nu: + (ii) R-L NaOMe (i) (ii) H Br CH3 (b) Competition experiments are those in which two reactants at the same concentration (or one reactant with two reactive sites) compete for a reagent. Predict the major product resulting from each of the following competition experiments: NaSH DMSO K'OCH(CH3)2 in propanol, 97 °C I DMF acetone H₂O Acetone CH3 RT H+CI C₂H5 MeOH heat, reflux (c) Suggest the shortest synthetic schemes for each of the following transformations. More than one step is required in each case. Show the reagents, solvents, reaction conditions, and intermediates for each step clearly. Please do not write reaction mechanisms. + R-L 28th April 2022 ? ? ? ? (d) What would be the effect of increasing solvent polarity on the rate of each of the following nucleophilic substitution reactions? CH3 HCN C₂H5 OH R-Nu RⓇ + 3G + :L L 1 A

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CHE 2511 BASIC ORGANIC CHEMISTRY
QUESTION ONE
(a) The following reactions either proceed through an E2 or an SN2 mechanism. Give the major
product of the following bimolecular reactions.
(i)
(ii)
(iv)
Jok
(ii)
E
OTS
(i) CI
*OK* + CH₂-Br
H₂C-CH₂
CI
CH3
x
(i) Nu:
+
(ii) R-L
NaOMe
(i)
(ii)
H
Br
CH3
(b) Competition experiments are those in which two reactants at the same concentration (or
one reactant with two reactive sites) compete for a reagent. Predict the major product
resulting from each of the following competition experiments:
NaSH
DMSO
K'OCH(CH3)2
in propanol, 97 °C
I
DMF
acetone
H₂O
Acetone
CH3
RT
H+CI
C₂H5
MeOH
heat, reflux
(c) Suggest the shortest synthetic schemes for each of the following transformations. More
than one step is required in each case. Show the reagents, solvents, reaction conditions,
and intermediates for each step clearly. Please do not write reaction mechanisms.
+ R-L
28th April 2022
?
?
?
?
(d) What would be the effect of increasing solvent polarity on the rate of each of the
following nucleophilic substitution reactions?
CH3
HCN
C₂H5
OH
R-Nu
RⓇ
+
3G
+ :L
L
1
A
Transcribed Image Text:5:08 Back CHE 2511_Tutorial S... CHE 2511 BASIC ORGANIC CHEMISTRY QUESTION ONE (a) The following reactions either proceed through an E2 or an SN2 mechanism. Give the major product of the following bimolecular reactions. (i) (ii) (iv) Jok (ii) E OTS (i) CI *OK* + CH₂-Br H₂C-CH₂ CI CH3 x (i) Nu: + (ii) R-L NaOMe (i) (ii) H Br CH3 (b) Competition experiments are those in which two reactants at the same concentration (or one reactant with two reactive sites) compete for a reagent. Predict the major product resulting from each of the following competition experiments: NaSH DMSO K'OCH(CH3)2 in propanol, 97 °C I DMF acetone H₂O Acetone CH3 RT H+CI C₂H5 MeOH heat, reflux (c) Suggest the shortest synthetic schemes for each of the following transformations. More than one step is required in each case. Show the reagents, solvents, reaction conditions, and intermediates for each step clearly. Please do not write reaction mechanisms. + R-L 28th April 2022 ? ? ? ? (d) What would be the effect of increasing solvent polarity on the rate of each of the following nucleophilic substitution reactions? CH3 HCN C₂H5 OH R-Nu RⓇ + 3G + :L L 1 A
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