Textbook Question
Show how you would synthesize the following primary alcohol by adding an appropriate Grignard reagent to formaldehyde.
(a)
13. Alcohols and Carbonyl Compounds
Grignard Reaction
3:39 minutesProblem 28
Textbook Question
Which of the following alkyl halides could be successfully used to form a Grignard reagent?
Verified step by step guidance1
Identify the general structure of a Grignard reagent. A Grignard reagent is an organomagnesium compound with the formula \( \text{R-MgX} \), where \( \text{R} \) is an alkyl or aryl group and \( \text{X} \) is a halogen (Cl, Br, or I).
Understand the conditions required for the formation of a Grignard reagent. The alkyl halide must not contain functional groups that are reactive with the Grignard reagent itself, such as \( \text{-OH} \), \( \text{-NH_2} \), \( \text{-COOH} \), or \( \text{-C=O} \), as these groups can react with the highly nucleophilic \( \text{R-MgX} \).
Evaluate the alkyl halides provided in the problem. Check if the halogen is attached to a carbon atom that is not sterically hindered or part of a highly reactive functional group. Primary and secondary alkyl halides are generally suitable, while tertiary alkyl halides may not work well due to steric hindrance.
Ensure that the halogen in the alkyl halide is suitable for Grignard reagent formation. Chlorine (Cl), bromine (Br), and iodine (I) are commonly used, while fluorine (F) is generally not reactive enough to form a Grignard reagent.
Exclude any alkyl halides that contain incompatible functional groups or structural features, and identify the ones that meet all the criteria for successful Grignard reagent formation.
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Key Concepts
Here are the essential concepts you must grasp in order to answer the question correctly.
Grignard Reagents
Grignard reagents are organomagnesium compounds formed by the reaction of alkyl or aryl halides with magnesium metal in dry ether. They are highly reactive nucleophiles used in organic synthesis to form carbon-carbon bonds. The general formula for a Grignard reagent is R-MgX, where R is an alkyl or aryl group and X is a halogen.
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Alkyl Halides
Alkyl halides are organic compounds containing a carbon chain bonded to a halogen atom (F, Cl, Br, or I). The reactivity of alkyl halides in forming Grignard reagents depends on the type of halide and the stability of the resulting reagent. Primary alkyl halides are generally preferred for Grignard formation, while tertiary halides often lead to elimination reactions instead.
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Nucleophilicity and Reactivity
Nucleophilicity refers to the ability of a species to donate an electron pair to an electrophile, which is crucial in the formation of Grignard reagents. The reactivity of alkyl halides in this context is influenced by steric hindrance and the leaving group ability of the halide. Stronger nucleophiles and better leaving groups facilitate the formation of Grignard reagents, making the choice of alkyl halide critical.
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