Chapter 21: 68P (page 817)
Draw a stepwise mechanism for the following reaction that converts a dicarbonyl compoundto a furan.
Short Answer

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Chapter 21: 68P (page 817)
Draw a stepwise mechanism for the following reaction that converts a dicarbonyl compoundto a furan.

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:(a) Give the IUPAC name for A and B. (b) Draw the product formed when A or B is treated with each reagent: [1] NaBH4 [2] CH3MgBr then H2O ; [3] Ph3P=CHOCH3 ;[4] CH3CH2CH2NH2mild acid; [5] HOCH2CH2CH2OH,H+ .

Which compound in each pair forms the higher percentage of gem-diol at equilibrium?
a.
or

b.
or

What reagents are needed to convert each compound into butanal (CH3CH2CH2CHO )?
a.

b.

c.

Explain why benzaldehyde is less reactive than cyclohexanecarbaldehyde towards nucleophilic attack.

Treatment of (HOCH2CH2CH2CH2)2CO with acid forms a product of molecular formula C9H16O2and a molecule of water. Draw the structure of the product and explain howit is formed.
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