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Orgo 18
Organic Chemistry
| Question | Answer |
|---|---|
| The carbon of the carbonyl group is s____ hybridized. The C=O bond is ______, ______ and ______ than C=C bonds. | p2; shorter, stronger, more polar |
| Ketones and Aldehydes have a _____ BP than comparable alkanes and ethers, and a ____ boiling point than comparable alcohols because they don't ______. | higher BP than alkanes and ethers; lower BP than alcohols; hydrogen-bond |
| Ketones and aldehydes are a good solvent for ______ because the lone pair of electrons on carbonyl oxygen can accept a ________ bond from O-H or N-H. | alcohols; hydrogen |
| Acetone and _______ are miscible with water. | acetaldehyde |
| Aldehydes and ketones show strong IR absorption between ____-____. The H-NMR of Aldehyde shows a signal at ______-_____, and the alpha carbon of aldehydes and ketones shows a signal at ___-____. | IR 1630-1810; H-NMR 9.5-10.1; C-NMR 2.2-2.6 |
| The carbonyl carbon of aldehydes and ketones is identifiable by the position of its signal in C NMR between ____-____ | 180-210 |
| Aldehydes and ketones with sufficiently long carbon chains under go _________ rearrangement, which involves a cyclic flow of electrons in a six-membered ring transition state. There is a loss of an _____ (even mass number). | McLafferty; alkene |
| Secondary Alcohol + Chromic Acid -> _____ | ketone |
| Primary Alcohol + PCC -> _____ | aldehyde |
| Ozonolysis of Alkenes -> ______ | mixture of aldehydes and ketons depending on alkene substituents |
| Acid Chloride/AlCl3 + Benzene (Friedel-Crafts)-> _______ | Ketone |
| CO + HCl + AlCl3/CuCl + Benzene (Friedel-Crafts) -> ________ | benzaldehyde |
| Terminal Alkyne + (HgSo4, H2SO4, H20) -> ____ | methyl ketone (follows Markovnikov) |
| Terminal Alkyne + (Sia2BH, H2O2/NaOH) -> ____ | aldehyde (anti-Markovnikov) |
| Remove H+ from 1,3-Dithiane using ______. Alkylate with ______________, then _________. This gives ______. Repeat steps to get a __________. | BuLi; primary alkyl halide; hydrolyze; an aldehyde; ketone |
| Organolithium compounds attack the _____ and form a _____. Neutralization with aqueous acid produces an unstable _____ that loses water to form a ketone. | carbonyl; diion; hydrate |
| In the synthesis of ketones from Nitriles, A Grinard or Organolithium reagent attacks the _______ carbon (_____ attack). The ____ salt is then _______ to form a ketone. | nitrile; nucleophilic; imine; hydrolyzed |
| To form an aldehyde from Acid Chlorides, use a mild _____ agent to prevent ____ to primary alcohol. A good reagent is ___________. | reducing; reduction; LiAlH (O-t-Bu)3 |
| To form Ketones from Acid Chlorides, use ___________, formed by the reaction of 2 moles of R-Li with cuprous iodide. This is called a ____ reaction. | Lithium DiAlkylcuprate (R2CuLi); Gilman |
| One of the most common reaction themes of a carbonyl group is addition of a _______ to form a _______ carbonyl addition compound. | nucleophile; tetrahedral |
| A strong nucleophile attacks the carbonyl carbon, forming an __________ ion that is then _________. | alkoxide; protonated |
| A weak nucleophile will attack a carbonyl if the C=O group has been ___________, thus increasing its reactivity. Aldehydes are ______ reactive than ketones. | protonated; more |
| What is the trend of Carbonyl Reactivity with a Nucleophile? | Formaldehyde > Aldehyde > Ketone > Ester |
| The Wittig reaction is a very versatile synthetic method for the synthesis of _______ from aldehydes and ketones. It works by the ______ addition of phosphorus _____. | alkenes; nucleophilic; ylides |
| _________ is a molecule which has positive and negative charges on adjacent atoms (in a Lewis Structure) | Ylide |
| In a Wittig Reaction, the negative C on the ____ attacks the positive C of the ________ to form a _______. Oxygen combines with Phosphine to form the _______________. | Ylide; Carbonyl; betaine; phosphine oxide |
| The addition of water of a carbonyl group of an aldehyde or ketone forms a __________, commonly referred to as a ________. Formalehyde is much ____ likely than ketones to be hydrated. | 1,1-diol, hydrate |
| For hydrations in acid, _______ is the nucleophile. For hydrations in base, _______ is the nucleophile. Aldehydes are more _______ and therefore ____ stable than ketones. Aldehydes are ___ likely than ketones to form stable hydrates. | water; hydroxide; electophilic; less stable than ketones; more likely to form stable hydrates |
| _____ adds to the C=O group of an aldehyde or ketone to give a cyanohydrin. Cyanohydrin is a molecule containing an ____ and a ____ group bonded to the same carbon. The mechanism is a ____-catalyzed ____ addition. | HCN; -OH, -CN; base-catalyzed nucleophilic addition |
| The reactivity trend of ketones and aldehydes in cyanohydrin formation (reversible process): | Formaldehyde > aldehydes > ketones>> bulky ketones |
| Ammonia, Primary aliphatic amines, and primary aromatic amines react with the C=O group of aldehydes and ketones to give ________ + ____. | Imines, water |
| Formation of an imine occurs in two steps. Step 1: _____-catalyzed addition of the ____ to the carbonyl group. Step 2: acid-catalyzed _______ | acid-catalyzed; amine; dehydration |
| The proper ___-- is crucial to imine formation. The second mechanism is acid-catalyzed, so it must be somewhat acidic. It can't be too acidic, otherwise the amine becomes protonated and non-nucleophilic. An ideal pH is ____. | pH; 4.5 |
| Aldehyde or Ketone + 2 Alcohol -> _____ + ____ | acetal + H20 |
| _______ is a molecule containing two -OR or -OAr groups bonded to the same carbon. | Acetal |
| Acetal formation MUST be ____-catalyzed because it promotes the first step, which is ________ of the carbonyl group. Then the ____ attacks, followed by loss of a proton to give a _____. | Acid-catalyzed; protonation; alcohol; hemicetal |
| Hemiacetals are too unstable to be isolated and purified. Following hemiacetal formation, _______ of the hydroxyl group, followed by loss of ____, gives a resonance-stabilized _______. An ____ attacks, followed by loss of a ____, giving the acetal. | protonation; water; carbocation; carbocation; alcohol; proton |
| All the steps of the formation of acetals are _______ and the ______ constant determines the proportions of reactants and products present at equilibrium. | reversible; equilibrium |
| Formation of an acetal using a _______ as the alcohol gives a cyclic acetal. These have a favorable equilibrium constant. ________ commonly exist as acetals or hemiacetals. | diol; Sugars |
| ___ hydrolyze easily in acid, but are very stable in base and nucleophiles. They are easily converted from ketones and aldehydes and back, making them good ____ groups to keep ketones and aldehydes from reacting w/ strong bases and nucleophiles. | Acetals; protective |
| Aldehydes form ______ more readily than ketones, so aldehydes can be protected selectively in the presence of a ketone. This leaves the ketones available for modification under ____ or ___ conditions without disturbing the more reactive aldehyde group. | acetals; neutral or basic |
| Unlike ketones, aldehydes are easily oxidized to _______, by common oxidants such as chromic acid or permanganate. Mild reagents such as ______ can oxidize aldehydes selectively in the presence of other oxidizable functional groups. | carboxylic acids; Ag2O |
| The _____ Test involves adding a solution of silver-ammonia complex to the unknown compound. If _____ are present, its oxidation reduces silver ion to metallic silver. | Tollens; aldehydes |
| Ketones and aldehydes are most commonly reduced by ______. This reduces ketones to ____ alcohols and aldehydes to ____ alcohols. It can reduce C=___ but not C=__ bonds. LiAlH4 is much stronger and difficult to handle | Sodium borohydride (NaBH4); ketones -> secondary alcohols; aldehydes -> primary alcohols; can reduce C=O but not C=C |
| Both alkene double bonds and carbonyl double bonds can be reduced by catalytic ________. The most common catalyst for this is ________. | hydrogenation; Raney Nickel |
| ________ replaces the carbonyl oxygen of an atom of a ketone or aldehyde with two hydrogen atoms, reducing the carbonyl group to a _____ group. | Deoxygenation; methylene (C=O to CH2) |
| The _________ reduction is used to reduce (deoxygenate) molecules that are stable in hot acid. It uses _______ with HCl and H2O as the reactancts/solvents. Benzene rings are stable. | Clemmensen; Zn(Hg) |
| The ________ reduction is used to reduce molecules that are stable in very strong base. Use a ___ solvent, and a strong base such as KOH. | Wolff-Kishner; high-boiling |
Created by:
jgold37