High School

Starting with the molecule in the center, show the product of each reaction below. Note that each molecule has more than one functional group.

1) [tex] \text{LiAlH}_4 [/tex]
2) [tex] \text{H}_2\text{O} [/tex]
3) [tex] \text{H}_2\text{CrO}_4 [/tex]

6.
a. Draw the structure of any Grignard reagent.
b. Explain why a Grignard reagent is considered a nucleophile.

Answer :

The product of the reaction of [tex]C_6H_5CH_2OH[/tex] with [tex]LiAlH_4[/tex] is [tex]C_6H_5CH_2H[/tex], [tex]C_6H_5CHO[/tex] with [tex]LiAlH_4[/tex] is [tex]C_6H_5CH_2OH[/tex], [tex]C_6H_5CHO[/tex] with [tex]H_2CrO_4[/tex] is [tex]C_6H_5COOH[/tex]. (a) A Grignard reagent is an organometallic compound. (b) Grignard reagents are considered nucleophiles because they have a carbon atom with a partial negative charge.

[tex]LiAlH_4[/tex] is a reducing agent that can reduce aldehydes and ketones to alcohols. It can also reduce carboxylic acids to primary alcohols. The reaction of [tex]C_6H_5CH_2OH[/tex] with [tex]LiAlH_4[/tex] proceeds as follows:

[tex]C_6H_5CH_2OH + LiAlH_4 \rightarrow C_6H_5CH_2H + LiAl(OH)_4[/tex]

The reaction of [tex]C_6H_5CHO[/tex] with [tex]LiAlH_4[/tex] proceeds as follows:

[tex]C_6H_5CHO + LiAlH_4 \rightarrow C_6H_5CH_2OH + LiAl(OH)_4[/tex]

The reaction of [tex]C_6H_5CHO[/tex] with [tex]H_2CrO_4[/tex] proceeds as follows:

[tex]C_6H_5CHO + H_2CrO_4 \rightarrow C_6H_5COOH + H_2O + Cr_2(SO_4)_3[/tex]

In this reaction, [tex]H_2CrO_4[/tex] is an oxidizing agent that oxidizes the aldehyde group to a carboxylic acid group.

(a) The structure of a Grignard reagent can be shown as follows:

R-Mg-X

where R is an alkyl or aryl group and X is a halogen. The carbon atom in the R group has a partial negative charge because it has been de-protonated by the magnesium atom. This makes the carbon atom electron-rich and able to donate electrons to electrophiles.

(b) Grignard reagents are therefore considered nucleophiles, which means that they are electron-rich species that can attack electrophiles. This makes them useful in a variety of organic reactions, including the addition of carbon-carbon bonds, the synthesis of alcohols, and the formation of carbonyl compounds.

Learn more about Grignard reagents here:

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