Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic products. 1. Predict the products that would be formed from such a reaction A. 1-pentene (80%) and 2-pentene (20%) B. 1-pentene (20%) and 2-pentene (80 %) C. 1-pentene (50 %) and 2-pentene (50 %) D. 1-pentene (0 %) and 2-pentene (100 %) E. 1-pentene (100 %) and 2-pentene (0 %) 2. What reaction pathway is followed by the reaction above? A. E2 dehydrohalogenation B. E1 dehydrohalogenation C. SN1 dehydrohalogenation D. SN2 dehydrohalogenation E. A mixture of E1 and E2 pathways 3. What is responsible for the formation of different products (major and minor). A. The different activated complex involved in the mechanism. B. Bimolecular Nucleophilic substitution reaction C. Bimolecular Elimination reaction D. The presence of sodium ethoxide E. The hybridisation nature of the secondary carbocation 4. All the following is true about the reaction in question 1 except? A. The reaction follows Zaistev’s rule B. Sodium ethoxide is the nucleophile in this reaction C. The more highly substituted alkene is the most stable product D. Dehydrohalogenation reaction of the alkyl halide is an elimination reaction E. The starting material (reactant) is a secondary alkyl halide 5. All the following parameters would affect the rate and kinetics of the reaction except A. Solvent medium B. Reaction temperature C. Reaction time D. Geometry and structure of the alkyl halide E. pH 6. What would be the major product when 2-iodopentane is involved in a dehydrohalogenation reaction? A. 2-iodo-1-pentene B. 2-pentene C. (E)-2-pentene D. (Z)-2-pentene E. Cis-2-pentene

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter16: Aldehydes And Ketones
Section: Chapter Questions
Problem 16.26P: Wittig reactions with the following -chloroethers can be used for the synthesis of aldehydes and...
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Preamble: A reaction flask contains a 2-bromopentane in an ethanolic solution of sodium ethoxide at room temperature and results in the formation of two olefinic products.
1. Predict the products that would be formed from such a reaction

A. 1-pentene (80%) and 2-pentene (20%)
B. 1-pentene (20%) and 2-pentene (80 %)
C. 1-pentene (50 %) and 2-pentene (50 %)
D. 1-pentene (0 %) and 2-pentene (100 %)
E. 1-pentene (100 %) and 2-pentene (0 %)


2. What reaction pathway is followed by the reaction above?
A. E2 dehydrohalogenation
B. E1 dehydrohalogenation
C. SN1 dehydrohalogenation
D. SN2 dehydrohalogenation
E. A mixture of E1 and E2 pathways

3. What is responsible for the formation of different products (major and minor).
A. The different activated complex involved in the mechanism.
B. Bimolecular Nucleophilic substitution reaction
C. Bimolecular Elimination reaction
D. The presence of sodium ethoxide
E. The hybridisation nature of the secondary carbocation

4. All the following is true about the reaction in question 1 except?
A. The reaction follows Zaistev’s rule
B. Sodium ethoxide is the nucleophile in this reaction
C. The more highly substituted alkene is the most stable product
D. Dehydrohalogenation reaction of the alkyl halide is an elimination reaction
E. The starting material (reactant) is a secondary alkyl halide


5. All the following parameters would affect the rate and kinetics of the reaction except
A. Solvent medium
B. Reaction temperature
C. Reaction time
D. Geometry and structure of the alkyl halide
E. pH

6. What would be the major product when 2-iodopentane is involved in a dehydrohalogenation reaction?
A. 2-iodo-1-pentene
B. 2-pentene
C. (E)-2-pentene
D. (Z)-2-pentene
E. Cis-2-pentene
Preamble: A student chemist in an attempt to synthesise compound B from the aromatic aldehyde. Use the flow equation to answer Q25-28

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