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7/31/2019 Orgo 2 Guide
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ORGO 2 GUIDE
General Note: Some of these questions have been previously used in examples,etcetera, but they cover the things that I think are important to know from thissemester. Try to work through them with as few resources as possible, and we
will go through this at the final review.
Chem 210 Stuff
Identify all the chiral centers in this molecule and label them all R/S:
H
BrO
NH2
OH
Show the mechanism of the following reaction:
CH3I
B:-
Chapter 13
Draw the complete oxidation sequence of methane (hint, it starts with oxygeninsertion to make methanol) into carbon dioxide and water.
What are the reagents necessary for Swern Oxidation? What is the benefit of thisreagent set?
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Show the mechanism for the following oxidation reaction (use a Bronstead acidbase as necessary):
OH
Cr
O
O
OHHO
What color is Cr+6? Cr+3? What does adding Cr+6 to a substance determine?
What is required to oxidize an aldehyde to a carboxylic acid?
Predict the products of the following reactions; say what type of reaction theyare and identify the functional groups involved:
Cl
CH3OH
B:-
CH3CH2CH2OH
NaH CH3I
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Paying attention to stereochemistry, predict the following intramolecular
reactions:
OH
I
NaH
I
OH
NaH
Draw the reactive conformation chair form for the following intramolecular
substitution reaction (initial stereochemistry not shown, show what it has to be)and predict the product:HO Br
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Show the following mechanism (draw out TsOH at least once in yourmechanism) keeping track of the radioactive tracer:
CH3CH3CH218OH
TsOH NaCl (a source of Cl-)
Including stereochemistry predict the product of the following epoxide ringopening reactions:
Cl
OH3C
H
Cl
OH3C
H
NaOCH2CH2CH3
HOCH2CH2CH3
Cat. H2SO4
HOCH2CH2CH3
Why do we put in propanol with propanoxide in the top reaction as the solvent?
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Chapter 14
Predict the product of the following reactions:
MgBr
Cl
OH
O
O
Draw out the following mechanism:O
CH3CH2SH
H-B (cat.)
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Predict the product of the following reactions (assume an acid workup of allreactions):
H
H
O
O
O
O
NaH
LiAlH4
NaBH4
C-Li
Draw the mechanism of the following imine formation reaction:
O
H2N
H-B
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Predict the two organic products of the following reaction:
OO
H2O/H3O+
Predict all possible products from the following reaction (Hints: 1- There is onefor the cis formation and one for the trans formation (therefore stereochemistryis important) 2- One never works with a single molecule 3-No acid is available):
O Br
NaBH4
Which is more reactive, formaldehyde or propanal? Why?
What is the byproduct of all of the reversible nucleophile reactions in thischapter? How does this help increase the reversibility of these reactions?
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Chapter 15
Draw the reaction mechanism to form the acid chloride from the followingstarting material (picking the other reactant):
OH
O
List three ways to make a carboxylic acid:
Perform the following base condition mechanism:
Cl
ONaOH/H2O
Perform the following acidcondition mechanism and circle the importantintermediate:
Cl
OH3O
+/H2O
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Predict the product of the following reaction:
Cl
O
+
O
O
Show the mechanism of the following esterification reaction, and explain why thealcohol doesnt attack directly.
Cl
O
N
OH
This is a bit of an odd reaction, but think logically. Using your knowledge ofChem 210 and 215 predict the product of the following reaction:
O3 Ag2O
NaOH
H3O+
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Predict the product of the following reaction (hint: think intramolecular)
HO
O
O
1) NaBH42) H3O
+
Perform the following mechanism:
O
ONH2CH2CH3
H-B
Because your professors seem to love ita transesterification mechanism!
O
OCH3CH2CH2CH2CH2OH
H-B
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Chapter 16
Find all 5 tautomers of the following compound:
H
H
H
C
C
HH
C
OC
H
H
HO O
Show the following enol formation mechanisms:
O
H 3O
+
/H 2O
NaOH/H 2O
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Predict the product of the following set of proton transfers:O O
D2O
Show the mechanism for the following reaction:O
I
H2O
Show the mechanism of the following reaction:
Br
O O
NaOCH3/CH3OH
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Chapter 17
Form an enol from the following molecule under acid conditions:O
Use that enol with the following aldehyde and show the aldol condensationreaction (show the mechanism):
O
Show the following decarboxylation reaction (draw in the curved arrows):
OH
O
O
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Predict the products of the following retroaldol reaction:OHO Bronstead Base
Carbohydrates
What is the generic structural formula for a carbohydrate?
Draw the Fisher-projection of the simplest carbohydrate, name it. Then show theACID catalyzed mechanism of its tautomerization to its ketose form and namethat:
What size ring is the kinetically favored hemi-acetal of a aldohexose?Thermodynamically favored?
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Show the ACID catalyzed mutorotation of the following molecule:
CH3
OH
N
Draw the both products of an ACID catalyzed reaction of B-D Glucopyranose,circle the major product.
Draw a sugar that if it was added to a solution of CuSO 4 (which is blue/green)the solution would turn red and a precipitate would form. If you know it, what isthat precipitate?
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Draw the product of the following reactions and predict the number ofstereoisomers present in solution:
O
OH
HO
HO
OH
LiH
CH3CH2CH2Cl
O
OH
HO
HO
OH
HCl
NH2
What is a glycoside?
What is the result of the Tollins test for the following sugar?
O
H3CO
H3CO
H3
CO
OCH3
O
O H
H O
H O
O H
H C l
CH 3C H 2C H 2O H
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Draw an B(1->4) linkage of galactopyranose (the C-4 epimer of glucose) andglucopyranose (this is lactose):
Draw an a(1->4) linkage of two glucopyranose molecules (this is maltose):
What is poly-a-glucose? Poly-b-glucose?
Amino Acids and Proteins
NOTE: I am going to use any amino acid I want, if you dont know what it lookslikelook it up, it is good to get used to using anything they might throw at you.
Draw the amino acid Gly at physiologic pH (~6.5), what is this form of amolecule called?
Draw the titration curve for the amino acid Glu, draw the structure of themolecule at every important point:
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Predict the product of the following reaction:
Lys + SOCl2 ->
Draw the tripeptide GlnHisThr at pH 9:
Circle all the amino acids in the following list with hydrophilic sidechains:
Arg Leu Ile Glu Ser GlyPro Asp Val Met
Fill in the following blanks in the protecting group charts:
NH3 H
R
COH
O
NH3 H
R
COCH3
O
NH3 H
R
COCH2Ph
O
NH3 H
R
COC
O
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NH3 H
R
COCH3
O
NH3 H
R
COCH2Ph
O
NH3 H
R
COC
O
R
HH3N
COH
O
R
HH3N
COH
O NH
H
COH
R
O
Ph
O
O
NH
H
COH
R
O
O
O
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NH
H
COH
R
O
Ph
O
O
NH
H
COH
R
O
O
O
H3N H
R
COH
O
If given a choice of one of the following which is the most convenient to use andwhy?
CBzPheAlaOtBu CBzPheAlaOMe BocPheAlaOtBu
Draw the mechanism for removal the methyl ester protecting group from GlyOMe
Draw DCC:
What is the purpose of using DCC?
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Draw the mechanism for the reaction between CBzPhe and AlaOtBu using DCC toform CBzPheAlaOtBu:
What is the direction of synthesis of a protein in a machine? In nature?
What is the base material amino acids are connected to in solid state synthesis?
What is the primary structure of a protein? Secondary? Tertiary? Quaternary?
What is the most common kind of crosslinkage in protein structure? What aminoacids is it between?
What is the purpose of enzymes?
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DNA
Draw the mechanism for the reaction between NAD+ and ethanol. What is theproduct?
Which direction does a DNA chain grow in?
How many H-bonds hold together Guanine and Cytosine?
Which base appears in RNA but not DNA?
Which carbon has its OH replaced by H in DNA?
Draw the dinucleotide made up of thymine and adenine as it would appear inDNA:
What is PG-Cl (draw it)? What is it used for in DNA synthesis?
NOTE: Due to lack of notes on this section there is more you probably need toknow, but I wanted to get this done in time for you to start it.
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Naming
Name all of the following molecules using IUPAC naming. If marked with a Talso give their common (trivial name) and IUPAC name. If a name is given, drawthe molecule. Stereochemistry is important if implied by the name or structure.
HO
O
OH
CH3OH
Cl
T:
O
T: HOH2C CH2OH
O
OH
O
Br
OH
O
O
OH
OH
Cl
HO
O
O
OCH3
OCH3
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T:
O
OHHO
O
T: O
OO
HC N
CH3
CH3
O
(2R, 3R)-2,3,4 trihydroxybutanal (give trivial name also)
Propanoyl butanoate m-bromoacetophenone
Tetrahydrofuran Diethylene glycol dimethyl ether (AKA: diglyme)
Benzophenone 2,4-dimethyl-3-oxo-5-phenoxyhexanoic acid
3-cyclohexeneone 2-hydroxypropanamide
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Isopentylbromide m,m-Diaminodiphenylmethane (I use this)
n-hexylmagnesiumbromide p-toluene sulfonic acid
Methanoic acid (also give trivial name) 2,4-dimethylcyclohexanecarboxylic acid
Potassium benzoate ethyl propanoate
2,4-dihydroxyhexanoylchloride 3-methylhexanenitrile
(9Z) Sodium octadec-9-enoate
Good luck all and dont hesitate to ask questions.E-mail:[email protected]: (248)302-1975
mailto:[email protected]:[email protected]:[email protected]:[email protected]