CHEM 3410: Alcohols And Phenols (Ch. 17)
24 Cards in this Set
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Reaction of Grignard reagent (in ether) with formaldehyde produces...
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primary alcohol
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SN2 reaction of alcohol with ____ proceeds with only one inversion of stereochemistry
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tosylate
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Reagent used to reduce carboxylic acids and ethers to primary alcohols
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1. LiAlH4, ether
2. H3O+
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Mono-substituted benzene rings have special absorption bands in the IR spectrum at:
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690-710 cm-1
and
730-770 cm-1
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Reagent used to convert primary or secondary alcohol into an alkyl chloride
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SOCl2 in ether
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Esters with grignard reagents produce:
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tertiary alcohols
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Reaction with ____ is used to protect alcohols in the presence of triethylamine to help form an alkoxide anion
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chlorotrialkylsilane (Cl-SiR3)
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Reaction of Grignard reagent (in ether) with ketone produces...
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tertiary alcohol
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Oxidize a primary alcohol directly into a carboxylic acid
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CrO3 and H3O+ in acetone
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Reagent used to reduce aldehydes and ketones to primary and secondary (respectively) alcohols
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1. NaBH4, ethanol
2. H3O+
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Alcohols undergo fragmentation in mass spectrometry by 2 characteristic pathways:
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alpha cleavage
and
dehydration
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Meta-substituted benzene rings have special absorption bands in the IR spectrum at:
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690-710 cm-1
and
810-850 cm-1
|
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Oxidize a primary alcohol into an aldehyde
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PCC (pyridinium chlorochromate) in CH2Cl2
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Reagent used to convert primary or secondary alcohol into alkyl bromide
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PBr3 in ether
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Carboxylic acids with grignard reagents produce:
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no reaction
|
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Oxidize phenol into benzoquinone
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Fremy's salt: (KSO3)2NO in H2O
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Para-substituted benzen rings have special absorption bands in the IR spectrum at:
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810-840 cm-1
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Alcohols have a strong C-O IR absorption at:
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1050 cm-1
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O-H IR stretching absorption at:
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3300 ot 3600 cm-1
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Reaction of Grignard reagent (in ether) with aldehyde produces...
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secondary alcohol
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Ortho-substituted benzene rings have special absorption bands in the IR spectrum at:
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735-770 cm-1
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Dehydrate tertiary AND secondary alcohols (turns -OH into a good leaving group)
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POCl3 in pyridine at 0 degrees Celsius
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Reduce quinone into hydroquinone
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SnCl2 (or NaBH4) in H2O
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Dehydrate tertiary alcohols
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H3O+ in THF at 50 degrees Celsius
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CHEM 3410: Chapter 14