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59 Cards in this Set
- Front
- Back
What is a common feature of Carboxylic acids and derivatives?
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They contain an acyl group bonded to an electrongeative atom or substituent, that can act as a LG.
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Three rules of naming carboxylic acids (RCO2H)?
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1. Replace -e w/ -oic acid
2. -CO2H carbon is # C1 3. Bonded to a ring (-CO2H) use carboxylic acid. ie cyclopent-1-ene carboxylic acid. |
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Name these acids
HCO2H CH3CO2H |
Formic acid
Acetic acid |
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Most carboxylic acids exists as _____ held together by 2 _____ bonds.
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dimer
hydrogen |
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T or F
Esters have a plesant smell and are present in animal fats? |
True
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What is the formula for an Ester?
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CH3CO2R
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T or F
Amids are least reactive of the common acid derivative and are thus stable. |
True
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What is the formula for Amids?
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NH2 is attached at some point.
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Are acid Chlorides and anhydrides found in nature?
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No
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Why are acid Chlorides and anhydrides not found in nature?
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They are highly reactive.
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What is the acidity of Carboxylic Acid? pKa =
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pKa = 4.76
Ka = 1.75x10^-5 |
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When Carboxylic acid react with NaOH, you get?
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a water soluble metal carboxylates RCO2- Na+
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Is Carboxylic Acid a stronger acid than alcohols and phenols?
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Yes.
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Why is Carboxylic Acid a stronger acid then alcohols and phenols?
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because the charge is spread across both O atoms due to resonance.
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T or F
The more stabilized the carboxylate anion, the stronger the acid. |
True.
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the synthesis of Carboxylic Acid oxidation is done using what two chemicals? and what does each add?
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done with KMnO4
adds 2 O's done with (the molecule has a C=O bond already) CrO3 and adds 1 O. |
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Nucleophilic Acyl Substitution Rxn.
Aldehyde or Ketone Nu: addition...explain the details |
Nu: attaches to C and double bond breaks. O has a (-) change now. H3O+ is added and the O takes an H creating an alcohol.
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Nucleophilic Acyl Substitution Rxn.
Carboxylic Acid derivative Nu: substitution |
Nu: attaches to C double bond breaks. O has a (-) charge now. the O e- go back onto the bond creating a double bond again and knocking off the LG.
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In a Nucleophilic Acyl Substitution Rxn., which step is the rate limiting one?
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the addition step.
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What does Acyl mean?
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RCO-
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An Aldehyde or Ketone Nu: addition ends in what CO bond?
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single bond
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An Carboxylic Acid Nu: substitution ends in what CO bond?
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double bond
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List the 5 common carboxylic acids from least reactive to most reactive.
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Amid
Ester Thioester Acid Anhydride Acid Cloride |
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Hydorlysis is a rxn with ____ and yeilds ______.
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H2O
Carboxylic Acid |
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Alcoholysis is a rxn with _____ and yields ______.
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-OH
Ester RC=OOR |
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Aminolysis is a rxn with _______ or an ______ and yields _____.
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ammonia or amine
Amide |
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Reductions is a rxn with ____ to yield _____.
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Hydride (hydrogen being nucleophilic ie. :H-) reducing agnet
-OH or alcohol |
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Grignard is a rxn with _____ to yield _______
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RMgX
-OH |
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Carboxylic Acids and Their rxns
Substitution is done using 2 methods. 1. 2. |
1. using strong acid to protonate (H3O) to give an -OH
2. convert -OH into a better LG. |
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Carboxylic Acids and Their rxns
to convert a Carboxylic Acid into an acid chloride you use what chemical? |
SOCl2
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Carboxylic Acids and Their rxns
to convert a Carboxylic Acid into an Ester you use what? |
Fisher esterification rxn.
The OH is removed and the CH3CH2OH is added. RC=OOCH2CH3 + H2O |
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Carboxylic Acids and Their rxns
Ester is formed when using an ______solvent. Carboxylic acid is formed when using an ______ solvent. |
-OH
H2O |
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Most of the chemistry of carbonyl compounds can be explained by 4 fundamental reactions. What are the first 2?
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1. The nucleophilic addition reaction of Aldehydes and Ketones
2. the nucleophilic acyl substitution reaction of carboxylic acid derivatives. |
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Review Exam 1:
Name each type of bond: 1. Equal sharing of electrons 2. Unequal sharing of electrons 3. no sharing of electrons at all |
1. Non polar covalent bond
2. polar covalent bond 3. Ionic Bond |
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Review Exam 1:
Pi bonds are made from the overlap of? |
the p orbital (at both ends)
They are sideways overlaped |
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Review Exam 1:
Sigma bonds are made up of the overlap of? |
the sp3-sp3 hybrid bond
They are end on end overlaped |
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Review Exam 1:
What is a lewis Acid and lewis Base |
Lewis acid it an electron acceptor, lewis base is an electron donor.
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An sp2 hybrid has what type of bond and what type of shape?
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Double bond
Trigonal planar shape. |
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Review Exam 1:
sp1 has how many equivalent sp orbitals and how many unhypridized |
2,2
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Review Exam 1:
sp2 has how many equivalent sp orbitals and how many unhypridized |
3,1
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Review Exam 1:
sp3 has how many equivalent sp orbitals and how many unhypridized |
4,0
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Review Exam 1:
state the Hand's Rule |
when empty orbitals of equal energy are available 1e- occupies each w/ parallel spins.
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Review Exam 1:
State Avfbau principal |
Start at the bottom and build your way up.
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Review Exam 1:
State the polyexclusion principal |
only 2e- w/ different spin can be in an orbital.
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Review Exam 1:
In Newman projections the staggard configuration is higher in energy. T or F |
False
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Review Exam 1:
In Newman projections the eclipsed configuration is higher in energy. T or F |
True, because the "clouds" are bumping.
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Review Exam 1:
In Newman projections which is more stable. Eclipsed or Staggered? |
Staggered is more stable.
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Review Exam 1:
What are steroisomers? |
Have the same formula and structure, but different in space due to bond rotation
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Review Exam 1:
What are constitutional isomers? |
Have the same formula, but different connections.
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Review Exam 1:
What is a cis isomer and a trans isomer? |
Cis = same side of the molecule
Trans = opposite side of the molecule. |
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Review Exam 1:
List what each scientist discovered. Kekule Watson & Crick Pauling Wohler |
Chemical structure
DNA structure Electronegativity Organic cmpd formed from inorganic cmpds. |
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Review Exam 1:
Saturated hydrocarbons have _____ hydrogens attached to the carbons |
the max number
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Review Exam 1:
What is a conformational isomer? |
The isomer can be interconverted due to the rotation of the C-C bond.
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The chair conformation of cyclohexane contain what type of strain.
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no strain
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Review Exam 1:
Angle strain you should think of? Steric strain you should think of? |
A cyclopropane
An Ethyl (Newman projection) |
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Review Exam 1:
In the chair conformation the axial bonds are? |
up and down/parallel
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Review Exam 1:
in the chair conformation the equitorial conformation bonds are? |
parallel to one bond over.
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Review Exam 1:
In the chair conformation the more stable conformation will have the largest molecule in the _____ bond |
equitorial
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Review Exam 1:
When prediction which side a reaction will favor the reaction runs to the side with the weak acid and weak base. T or F |
True
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