Chapter Ii In Depth (plus – Flashcards
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List the relative boiling points of carbonyl groups. Why are they this way?
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Amide > Carboxylic acid > Nitrile > (Ester~acyl chloride~aldehyde~ketone) > ether. Amides have the highest bp bc of the strong Dipole-Dipole interactions of resonance contributors and Hydrogen bonds form between the molecules. Caboxylic acids bc of intermolecular Hydrogen bonding and Nitriles bc of Dipole-dipole interactions.
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Draw the intermolecular Hydrogen bonding of Carboxylic acids.
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Draw the intermolecular Hydrogen bonding of Amides
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Draw the intermolecular bonding of Dipole-Dipole interactions in amides.
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draw the intermolecular Dipole-Dipole bonding in Nitriles.
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What is the difference in the smell between aldehydes and ketones?
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Aldehydes have pungent odors (like vanilla extract or cinamaldehyde) and Ketones tend to smell sweet (the sweet odors of spearment and caraway seed (carvone).
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What is Ketosis?
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A pathological condition that can occur in people with diabetes in treatment of paediatric epilepsy or on a ketogenic (very low carb diet like the Atkins diet and fatburning bodybuilding diets) when the body produces more acetoacetate than can be metabolized. The excess acetoacetate breaks down to acetone (the simplest ketone). Ketosis can be recognized by the smell of acetone on a person's breath.
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3-chlorobutanal (beta-chlorobutyraldehyde)
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trans-2-methylcylohexanecarbaldehyde
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(acetophenone) ((methyl phenyl ketone))
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Name Functional Group Priority Class, Suffix, Prefix
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Carboxylic (-oic,Carboxy) Ester (-oate, Alkoxycarbonyl) Amide (amide, Amido) Nitrile (-nitrile, Cyano) Aldehyde (al, Oxo ( =O ) Aldehyde (al, Formyl (CH=O) Ketone (-one, Oxo ( =O ) Alcohol (-ol, Hydroxy) Amine (-amine, Amino) Alkene (-ene, Alkenyl) Alkyne (-yne, Alkynyl) Ether (---, Alkoxy) Alkyl halide (---, Halo)
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What is the relative reactivity greatest to least of carbonyl compounds and why?
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Formaldehyde, Aldehyde, ketone. 1.) Hydrogen is more electron withdrawing so the carbonyl carbon charge will be more partial positive and more reactive to nucleophiles and therefore more reactive to nucleophilic addition. While alkyl groups more stabalize the ketone making it less reactive. 2.) Steric factors - hydrogen's small size make the carbonyl carbon on the aldehyde more accessible. Ketones have greater steric crowding in in their transition states. Therefore the alky groups on the ketone stabilize the ketone and destabilize the transition state making it less reactive than aldehydes
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What are the 4 types of nucleophilic addition reactions that aldehydes and ketones undergo? Why these three?
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irreversible (if the nucleophile is a strong base) reversible (if the nucleophile is a weak base) Addition-elimination (if the attacking nucleophile has a lone pair and there is enough acid in the solution to protonate the OH group of the tetrahedral compound then water can be eliminated from the addition product. This reaction is also reversible). Gringnard reactions Can also be considered a strong base reaction and is irreversible).
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how do you use Grignard reactions to form a) A primary Alcohol b) A secondary Alcohol c) A tertiary Alcohol d) A Carboxylic acid
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a) formaldehyde b) Aldehyde c) Ketone d) carbon dioxide ----------------------------> 1.R-Grignard 2. H3o+ (dilute acid)
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Why don"t grignard reagents add to the carbonyl carbon of a carboxylic acid?
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A carboxylic acid has an acidic proton that reacts first converting the reagent into an alkane.
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From ethyne Sythesize 1)1-pentyn-3-ol 2)1-phenyl-2-butyn-1ol 3) 2-methyl-3-hexyn-2-ol
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#1.) ethyne + NaNH2 2.)Propanal 3.) HCl #2) ethyne + NaNH2 2.) CH3MgBr (this gives Methylacetylene) 3) NaNH2 4)benzaldahyde 5) HCl #3)
