OTS NaCl DMSO 20°C NaOH DMF 75 °C H₂S EtOH 0°℃ Factor S1 Subst. of C Strength Nuc/B Solvent Temperature Total Factor S1 Subst. of C Strength Nuc/B Solvent Temperature Total Factor S1 Subst. of C Strength Nuc/B Solvent Temperature Total SN2 E1 E2 SN2 E1 E2 SN2 E1 E2

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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A competition table can be used to keep track of what conditions promote which reaction mechanism.
Factor S1 SN2 E1 E2
X X X
X X
X
X
.
Br.
The a-carbon is secondary sp³: works for all mechanisms.
Azide (NaN3) is a strong nucleophile and weak base: works for all substitutions and E1.
DMSO is an aprotic solvent: promotes all bimolecular reactions.
The temperature is less than room temperature: promotes substitution.
SN2 got the most Xs in the competition and wins: predict the product as an SN2.
Br
NaN
DMSO
15 °C
OTS
CI
CH₂OH
A
Br
OH
The a-carbon is tertiary sp³: works for SN1, E1, and E2.
Methanol (CH3OH) is a weak nucleophile and weak base: works for SN1 and E1.
NaCl
DMSO
20 °C
NaOH
DMF
75 °C
H₂S
EtOH
0 °C
N₂
EtOH
Subst. of C
Strength Nuc/B
Solvent
A
Temperature X
Total 3
H₂PO4
95 °C
KOMe
MeOH
-10 °C
Factor
Subst. of C
•
• No solvent is provided. Assume the nucleophile is also the solvent (sovolysis). Methanol is a protic solvent:
promotes all unimolecular reactions.
• The temperature is elevated: promotes elimination.
• Elgot the most Xs in the competition and wins: predict the product as an E1.
Strength Nuc/B
Solvent
Temperature
Using the provided competition factor tables, determine which mechanism each of the following reactions is
going to undergo and predict the major organic product(s) with the correct stereochemistry if necessary.
Total 3
Subst. of C
Strength Nuc/B
Solvent
Temperature
Total
S1
X
X
X
Strength Nuc/B
Solvent
Temperature
Total
X
X
4 2
SN2 E1
Strength Nuc/B
Solvent
Temperature
Total
X
E2
X X
X
X
X
2
04
Factor S1 S2 E1 E2
Subst. of C
Strength Nuc/B
Solvent
Temperature
Total
X
4 2
Factor S1 SN2 E1 E2
Subst. of C
Subst. of C
Strength Nuc/B
Solvent
Temperature
Total
Factor SN1 SN²2 E1 E2
Subst. of C
Factor S1 SN2 E1 E2
Subst. of C
Strength Nuc/B
Solvent
Temperature
Total
Factor S1 SN2 E1 E2
Factor S1 SN2 E1 E2
Transcribed Image Text:A competition table can be used to keep track of what conditions promote which reaction mechanism. Factor S1 SN2 E1 E2 X X X X X X X . Br. The a-carbon is secondary sp³: works for all mechanisms. Azide (NaN3) is a strong nucleophile and weak base: works for all substitutions and E1. DMSO is an aprotic solvent: promotes all bimolecular reactions. The temperature is less than room temperature: promotes substitution. SN2 got the most Xs in the competition and wins: predict the product as an SN2. Br NaN DMSO 15 °C OTS CI CH₂OH A Br OH The a-carbon is tertiary sp³: works for SN1, E1, and E2. Methanol (CH3OH) is a weak nucleophile and weak base: works for SN1 and E1. NaCl DMSO 20 °C NaOH DMF 75 °C H₂S EtOH 0 °C N₂ EtOH Subst. of C Strength Nuc/B Solvent A Temperature X Total 3 H₂PO4 95 °C KOMe MeOH -10 °C Factor Subst. of C • • No solvent is provided. Assume the nucleophile is also the solvent (sovolysis). Methanol is a protic solvent: promotes all unimolecular reactions. • The temperature is elevated: promotes elimination. • Elgot the most Xs in the competition and wins: predict the product as an E1. Strength Nuc/B Solvent Temperature Using the provided competition factor tables, determine which mechanism each of the following reactions is going to undergo and predict the major organic product(s) with the correct stereochemistry if necessary. Total 3 Subst. of C Strength Nuc/B Solvent Temperature Total S1 X X X Strength Nuc/B Solvent Temperature Total X X 4 2 SN2 E1 Strength Nuc/B Solvent Temperature Total X E2 X X X X X 2 04 Factor S1 S2 E1 E2 Subst. of C Strength Nuc/B Solvent Temperature Total X 4 2 Factor S1 SN2 E1 E2 Subst. of C Subst. of C Strength Nuc/B Solvent Temperature Total Factor SN1 SN²2 E1 E2 Subst. of C Factor S1 SN2 E1 E2 Subst. of C Strength Nuc/B Solvent Temperature Total Factor S1 SN2 E1 E2 Factor S1 SN2 E1 E2
10. For each of the following reactions, predict the major organic product, including stereochemistry where
appropriate. If the name of a reagent is given, draw the structure of that reagent.
a.
(S)-3-chlorooctane
f.
b. (S)-3-methyl-3-chlorooctane
TSO
OH
DMF
CH3CH₂OK
DMSO
EtOH
NaN3
EtOH
H3PO4
A
CH3CH₂OK
CH3CH₂OH
Transcribed Image Text:10. For each of the following reactions, predict the major organic product, including stereochemistry where appropriate. If the name of a reagent is given, draw the structure of that reagent. a. (S)-3-chlorooctane f. b. (S)-3-methyl-3-chlorooctane TSO OH DMF CH3CH₂OK DMSO EtOH NaN3 EtOH H3PO4 A CH3CH₂OK CH3CH₂OH
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