Exam 19: Aldehydes and Ketones: Nucleophilic Addition Reactions

Exhibit 19-3 Consider the reaction below to answer the following question(s). -Refer to Exhibit 19-3.The product of this reaction is called:

Exhibit 19-9 Consider the data below to answer the following question(s). C₇H₁₄O IR: 1715 cm−¹ MS: M⁺ at m/z = 114,α-cleavage fragment at m/z = 71, McLafferty rearrangement fragment at m/z = 86. ¹H NMR: 0.92 δ (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet) -Refer to Exhibit 19-9.Calculate the degree of unsaturation for this compound.

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Draw the mechanism of the Grignard reaction involving acetone and methyl magnesium chloride.​

​Draw the mechanism of the nucleophilic addition reaction of pentanal to give an alcohol.

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Exhibit 19-9 Consider the data below to answer the following question(s). C₇H₁₄O IR: 1715 cm−¹ MS: M⁺ at m/z = 114,α-cleavage fragment at m/z = 71, McLafferty rearrangement fragment at m/z = 86. ¹H NMR: 0.92 δ (6H,triplet),1.59 δ (4H,multiplet),2.36 δ (4H,triplet) -Refer to Exhibit 19-9.Propose a structure consistent with the spectral data presented above.

Exhibit 19-4 α,β-Unsaturated aldehydes and ketones can undergo reaction with nucleophiles at the β carbon,as shown below. -Refer to Exhibit 19-4.Draw a resonance form for the unsaturated carbonyl that accounts for this reactivity.