FL 6 - Chem/Phys Flashcards
Oxidation of aldehydes produces which functional group?
A strong oxidizing agent will likewise oxidize an aldehyde to a carboxylic acid.
Many of the stronger oxidizing agents such as KMnO4will transform aldehydes into carboxylic acids.Tollens’ reagent [Ag(NH3)2]+ is one such oxidant. A shiny mirror of metallic silver is deposited through oxidation of aldehydes to form carboxylic acids by Tollens’ reagent, so it is a frequently used test for aldehydes in qualitative analysis
When ketones are oxidized by Tollen’s reagent, what does the product look like?
Ketones are not oxidized by Tollens’ reagent, therefore no “product” is formed, so the treatment of a ketone with Tollens’ reagent in a glass test tube does not result in a silver mirror.
A ______ ______ can be oxidized to an aldehyde by a mild oxidizing agent (such as PCC) or to a carboxylic acid by a strong oxidizing agent like NaCr2O7.
A primary alcohol can be oxidized to an aldehyde by a mild oxidizing agent (such as PCC) or to a carboxylic acid by a strong oxidizing agent like NaCr2O7.
A ________ ______will be oxidized to a ketone by either a mild or a strong oxidizing agent.
A secondary alcohol will be oxidized to a ketone by either a mild or a strong oxidizing agent.
When aldehydes are oxidized by Tollen’s reagent, what does the product look like?
Many of the stronger oxidizing agents such as KMnO4will transform aldehydes into carboxylic acids.Tollens’ reagent [Ag(NH3)2]+ is one such oxidant. A shiny mirror of metallic silver is deposited through oxidation of aldehydes to form carboxylic acids by Tollens’ reagent, so it is a frequently used test for aldehydes in qualitative analysis
A ______ reducing agent, such as LiAlH4, can reduce a carboxylic acid directly to an alcohol.
A strong reducing agent, such as LiAlH4, can reduce a carboxylic acid directly to an alcohol.
Will NaBH4 reduce a carboxylic acid? Why/Why not?
A weak reducing agent, such as NaBH4 will not reduce carboxylic acids at all.
What types of reducing agents can produce alcohols?
Both mild and strong reducing agents can reduce aldehydes and ketones to primary and secondary alcohols, respectively.
What types of oxidizing agents + substrates can produce a ketone?
A secondary alcohol will be oxidized to a ketone by either a mild or a strong oxidizing agent.
An ____ configuration involves two groups immediately adjacent to each other, while _____ structures have two substituents separated by a single carbon. Finally, ____ diols include two –OH groups immediately across from each other on the ring.
An ortho configuration involves two groups immediately adjacent to each other, while meta structures have two substituents separated by a single carbon. Finally, para diols include two –OH groups immediately across from each other on the ring.
All carboxylic acid derivatives are formed through a ________ ________ reaction, and upon hydrolysis, they all _____________
All carboxylic acid derivatives are formed through a nucleophilic substitution reaction, and upon hydrolysis, they all convert back to their parent carboxylic acid.
_____________ are formed when carboxylic acids react with thionyl chloride (SOCl2), PCl3, or PCl5. They are the ______ reactive derivatives of carboxylic acid.
Acid chlorides are formed when carboxylic acids react with thionyl chloride (SOCl2), PCl3, or PCl5. They are the most reactive derivatives of carboxylic acid.
LiAlH4 is a (strong/weak) base and a (strong/weak) reducing agent
LiAlH4 is a strong base and a strong reducing agent
What will happen to a molecule that has both a ketone and a carboxylic acid when reacted with LiAlH3?
Both the ketone and the carboxylic acid will be reduced to alcohols. This is because LiAlH3 is not chemoselective and is a strong reducing agent.
What will happen to a molecule that has both a ketone and a carboxylic acid when reacted with BH3?
Only the carboxylic acid will be reduced to an alcohol. This is because BH3 is chemoselective.
Why is it difficult to synthesize an amide directly from a carboxylic acid?
Amides are the most stable (least reactive) of the carboxylic acid derivatives because the amino substituent is a very poor leaving group. In order to synthesize amides however, one cannot simply use the amino substituent as a nucleophile; as a relatively strong base, it will instead preferentially participate in an acid-base neutralization reaction with the acidic hydrogen of the organic acid.
Instead, one must first create an acid chloride, or an acid anhydride, to eliminate the confounding acidic hydrogen. Afterwards, one can proceed with a normal nucleophilic substitution.
In the conversion of a fatty acid to an ester, what functional groups are changed?
In the conversion of a fatty acid to an ester, we lose a hydroxyl group, and neither gain nor lose any other relevant functional groups.
This is the conversion of a carboxylic acid to an ester, in which the carboxylic acid -OH is replaced with an -OR.
The hydrocarbon tails of trans fats stack _____ densely than those of comparable cis fats.
As shown in the image below, the hydrocarbon tails of trans fats are very similar to those of saturated fatty acids, meaning that they stack together more densely than the corresponding cis fats. The denser, more stable stacking of trans fats means that they are more likely to be solids—and therefore less likely to be liquids—at room temperature. This property of trans fats makes them useful for inclusion in commercially produced baked goods because the stable solid state of trans fats contributes to longer shelf life. Unfortunately, trans fats have also been closely associated with an elevated risk of cardiovascular disease.
Will a -cis or a -trans fatty acid have a higher melting point?
Which is more likely to be a liquid at room temperature?
A -cis double bond in a fatty acid makes a kink, preventing stacking of multiple fatty acids, and significantly lowering the possible van der waals forces, lowering the melting point. Therefore, a -trans fatty acid, with its ability to stack, will have a higher melting point and will be more likely to be a solid at room temperature.
In gas-liquid chromatography, what compounds will have the highest retention time?
In gas-liquid chromatography, the sample is volatilized in a hot chamber. The higher the boiling point temperature, the more time the compound will spend at the beginning of the chamber waiting to get volatilized. Retention time is the time it takes for the sample to reach the detector. Therefore, the compound with the highest boiling point will have the highest retention time.
Reaction 1 releases 188.6 J, what is the ∆H of Reaction 2?
Reaction 2 is simply Reaction 1 run in reverse with the stoichiometric coefficients doubled. So when we’re told that Reaction 1 releases 188.6 J, that means its enthalpy change is -188.6 J. The reverse reaction would have an enthalpy change of +188.6 J, and if you double the stoichiometry, you must double this value to get +377.2 J.
Define an Arrhenius base
An Arrhenius base is a compound or element that releases hydroxide ions into a solution when dissolved in water.
Define a bronsted-Lowry base
The bronsted-Lowry base is a proton acceptor.
Define a Bronsted-Lowry acid
A Bronsted-Lowry acid is a proton donor.