a) Bromobenzene, 2-bromopropane, bromoethane
Interpretation:
The compounds bromoethane, 2-bromopropane and bromobenzene are to be ranked in the order of their reactivity in Williamson synthesis.
Concept introduction:
In Williamson synthesis, the primary
To rank:
The compounds bromoethane, 2-bromopropane and bromobenzene in the order of their reactivity in Williamson synthesis.
b) Chloroethane, bromoethane, 1-Iodopropene
Interpretation:
The compounds chloroethane, bromoethane and 1-iodopropene are to be ranked in the order of their reactivity in Williamson synthesis.
Concept introduction:
In Williamson synthesis, te alkoxuide reacts with primary alkyl halides through a SN2 mechanism. The requirements are thus a backside attack, a stronger nucleophile and a better leaving group. Among the halides, iodine is better leaving than bromine which in turn is a better leaving than chlorine. Vinyl halides are less reactive than alkyl halides.
To rank:
The compounds chloroethane, bromoethane and 1-iodopropene in the order of their reactivity in Williamson synthesis.

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Chapter 18 Solutions
EBK ORGANIC CHEMISTRY
- Q1: Predict the major organic product(s) of the following reactions. Include stereochemistry when necessary. Write NR if no reaction, try to explain. 1.) LDA, THF 2.) СОН CI OH H2SO4, heat OH m...... OH 1.) PCC, CH2Cl2 2.) CH3CH2MgBr, THF 3.) H3O+ 4.) TsCl, pyr 5.) tBuOK, tBuOH 1.) SOCI 2, CHCI 3 2.) CH3CH2ONA, DMF OH 1.) HBr 2.) Mg, THF 3.) H₂CO, THE 4.) H3O+ OH NaH, THFarrow_forwardWhat is the stepwise mechanism for this reaction?arrow_forwardDraw the major product of this reactionarrow_forward
- Please provide the IUPAC name for the compound shown herearrow_forwardProblem 6-29 Identify the functional groups in the following molecules, and show the polarity of each: (a) CH3CH2C=N CH, CH, COCH (c) CH3CCH2COCH3 NH2 (e) OCH3 (b) (d) O Problem 6-30 Identify the following reactions as additions, eliminations, substitutions, or rearrangements: (a) CH3CH2Br + NaCN CH3CH2CN ( + NaBr) Acid -OH (+ H2O) catalyst (b) + (c) Heat NO2 Light + 02N-NO2 (+ HNO2) (d)arrow_forwardPredict the organic product of Y that is formed in the reaction below, and draw the skeletal ("line") structures of the missing organic product. Please include all steps & drawings & explanations.arrow_forward
- Please choose the best reagents to complete the following reactionarrow_forwardProblem 6-17 Look at the following energy diagram: Energy Reaction progress (a) Is AG for the reaction positive or negative? Label it on the diagram. (b) How many steps are involved in the reaction? (c) How many transition states are there? Label them on the diagram. Problem 6-19 What is the difference between a transition state and an intermediate? Problem 6-21 Draw an energy diagram for a two-step reaction with Keq > 1. Label the overall AG°, transition states, and intermediate. Is AG° positive or negative? Problem 6-23 Draw an energy diagram for a reaction with Keq = 1. What is the value of AG° in this reaction?arrow_forwardProblem 6-37 Draw the different monochlorinated constitutional isomers you would obtain by the radical chlorination of the following compounds. (b) (c) Problem 6-39 Show the structure of the carbocation that would result when each of the following alkenes reacts with an acid, H+. (a) (b) (c)arrow_forward
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