A competition table can be used to keep track of what conditions promote which reaction mechanism.Factor S1 SN2 E1 E2X X XX XXX.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.BrNaNDMSO15 °COTSCICH₂OHABrOHThe 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.NaClDMSO20 °CNaOHDMF75 °CH₂SEtOH0 °CN₂EtOHSubst. of CStrength Nuc/BSolventATemperature XTotal 3H₂PO495 °CKOMeMeOH-10 °CFactorSubst. 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/BSolventTemperatureUsing the provided competition factor tables, determine which mechanism each of the following reactions isgoing to undergo and predict the major organic product(s) with the correct stereochemistry if necessary.Total 3Subst. of CStrength Nuc/BSolventTemperatureTotalS1XXXStrength Nuc/BSolventTemperatureTotalXX4 2SN2 E1Strength Nuc/BSolventTemperatureTotalXE2X XXXX204Factor S1 S2 E1 E2Subst. of CStrength Nuc/BSolventTemperatureTotalX4 2Factor S1 SN2 E1 E2Subst. of CSubst. of CStrength Nuc/BSolventTemperatureTotalFactor SN1 SN²2 E1 E2Subst. of CFactor S1 SN2 E1 E2Subst. of CStrength Nuc/BSolventTemperatureTotalFactor S1 SN2 E1 E2Factor S1 SN2 E1 E2 10. For each of the following reactions, predict the major organic product, including stereochemistry whereappropriate. If the name of a reagent is given, draw the structure of that reagent.a.(S)-3-chlorooctanef.b. (S)-3-methyl-3-chlorooctaneTSOOHDMFCH3CH₂OKDMSOEtOHNaN3EtOHH3PO4ACH3CH₂OKCH3CH₂OH

Reaction path of any reaction depends on multiple factors like -- nature of the substrate,…

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

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

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

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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Question

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

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