Organic Chemistry 2 - Exam 3
which will elute first from an ion exchange column packed with anionic sulfonate polystyrene using pH=6 buffer solution
1. Ninhdrin 2.PTH of alanine 3. Sanger's reagent
which one answer most accurately lists the reaction steps for this transformation
1. Sn+HCl 2. HONO +HCl 3. COpper (1) chloride
glutamic acid has a pl of
3.22
which one answer most accurately ranks the basicity of substituted anilines?
4-methoxyanaline> p-chloroanaline>p-nitroaniline
How many fragments are produced after cleaving the following peptide with Carboxypeptidase B?
A
Identify the reactant of the following reaction
A
What are these three compounds
A
What is the imine intermediate of the reaction below?
A
What is the major product of the following reaction?
A
What is the minor product formed from the Hofmann elimination reaction shown below
A
What is the missing reactant in the following transformation
A
What is the product of the reaction sequence shown below
A
Which of the following amines is the least basic, based on the pKa values of their conjugate acids
A.
Which of the following indicates the correct order of steps in a complete liquid phase hydrolysis protocol
A. C,A,B,D
What is the name of the reaction shown below
A. Fischer Esterification
What is the correct abbreviated name of this tripeptide
A. Gin-Tyr-Met
Which of the following BEST classifies the compounds shown below
A. i)Nitrosamine ii) Pyrrolidine iii)Pyrrole
Which of the following peptides will carboxypeptidase B cleave?
A. N-Thr-trp-Arg-C
which one answer best describes the N-terminal amino acid in the structure below
Arg
Identify the petidase needed to cleave the amino acid from the following peptide chain
B&C
Identify the three-;ester abbreviation of this amino acid
B. His
Which of the following indicates the reactant and product of a Gabriel Amine Synthesis
B. Reactant: phthalimide Product:Amine
Which is true about the basicity of the nitrogen lone pairs in the compound below?
B. The alkyl amine is more basic than the imine
Which of the following gives the best definition of pl?
B. The pH at which an amino acid exists predominantly in its zwitterionic form
All of the following are true about protein structure except
B. The secondary structure of a protein might be composed of many alpha-helices and beta-sheets
Choose the one product name (A-E) that represents an amine that CANNOT be formed from the LAH reduction of an amine
B. 2-pentanamine
Which of the following is a reactant and a major product of sandmeyer reaction
B. Reactant: Aryl diazonium Salt Product: benzene
What is the missing reagent in the reaction scheme below?
B. Cu(CN)
What is the IUPAC name of this amine?
B. N-Methyl-3-hexanamine
Choose the one answer that best describes the reaction steps needed to perform the overall chemical transformation shown below
C
What is the major form of the following amino acid at a pH of 9.5
C
What is the major product of this reaction?
C
What is the reactant of the reaction shown below?
C
What is the reactant of this reaction
C
What is the structure of Methionine at pH=8
C
What structure represents the amino acid with three-letter code pro?
C
Which of the following shows the correct structure of di-tert-butyl dicarbonate
C
what is the product of the reaction sequence shown below
C
Rank the order of basicity of the following organic compounds from most to least basic
C. (most basic) Piperidine>Pyridine>Pyrrole (least basic)
What is the approximate pH at which Glu exists in its Zwitterion form
C. 3.2
Choose the one answer (A-E) that best describes the basicity of the nitrogens in the HIV integrase inhibitor
C. Nitrogen #3 and #7 are the best bases
Which of the following are the reactant(s) are major product(s) of Azo coupling
C. Reactant: Aryl diazonium salt +Aniline Product: Azo compound
Which ENDOpeptidease is needed to complete the reaction below
C. Trysin
Which answer (A-E) best classifies and describes a physical property of the amine shown below?
C. A secondary amine that is soluble in tetrahydrofuran
Which of the following compounds is a weaker nucleophile? why?
C. Pyrrole because the lone pair is part of the aromatic system
Which factor best describes why compound 1 is more basic than compound 2
C. Inductive effect
1) HNO3, H2SO4 2)H2, Pd/C 3)NaNO2, HCl 4)Cu(CN)
D
Choose the one answer (A-E) that is the resonance form least likely produced from a lactic in acid
D
Choose the one answer that 1) names the correct reactant and 2) describes the reaction condition that cannot be used to form the product (shown)
D
Choose the one answer (A-E) that provides the correct IUPAC name for the amine product from the synthetic scheme
D. 3-ethyl-N-methyl-2-hexanamine
What two functional groups react to form a peptide bond?
D. Amine and Carboxylic Acid
Given the pKa data below, select the one statement that is most true
D. Arginine has a net positive charge in pH 5.4 buffer
Which of the following amino acid pairs has the strongest stabilizing interaction between their R groups (assuming both amino acids are in the same protein)
D. Cys-Cys
What is the common name of the following compound
D. Diethylmethylamine
What is the common name of the following compound?
D. Diethylmethylamine
How many fragments will be formed after cleaving the following peptide with Trypsin
D. 3
which one answer is not true about the use of DCC in peptide synthesis
DCC is used to protect the carboxyl group of C-terminal end of the peptide
Which one answer is not true about disulfide bridges
Disulfide bonds result from the reduction of two thiol groups
Choose the one answer that best ranks these compounds
E
Identify the polar acidic amino acid
E
What is the correct Fischer projection of this amino acid
E
What is the major product of the reaction shown below
E
What is the structure of Phenylalanine when pH=1
E
What is the structure of aspartic acid when the pH of the solution is 1
E
Which of the following most accurately describes the following compounds
E
Which of the following molecules is NOT soluble in organic solvents, but IS soluble in water?
E.
Choose the one process (A-E) that CAN be used to form a secondary amine
E. Hydrogenation of an imine
Which of the following correctly ranks these compounds in order of increasing boiling point?
E. (lowest BP) A<B<C(highest BP)
Which of the following reactions describes the BEST way to make a tertiary amine
E. An ally halide reacting with NH3
Which one answer (A-E) best describes the reactant and final product of this reaction scheme?
E. Reactant is an azido compound ; Final product is a secondary amine
Choose the one answer (A-E) that best describes the reaction condition that CANNOT produce the psychedelic drug, 2C-D
E. all of the above should work to produce 2C-D
Identify the EXOpeptidase needed to complete the reaction below
E. carboxypeptidase A
What is the best definition of an incomplete protein?
E. incomplete proteins lack one or more of the essential amino acids
Which one answer describes the best method to only deprotect the carboxyl group of the compound shown below?
E. H2+ Pd/Carbon
which one answer is not true about oxytocin
Gly is the N-terminal amino acid
Which one answer describes the best method to only deprotect the carboxyl group of the compound shown below
H2+Pd/Carbon
the Fischer projection shown below denotes a ___ amino acid which has the ___ configuration
L,S
Select the name for this compound below
N,N-diethyl-2-pentanamine
Which one answer best describes the structure shown below
N-acyl Fmoc-Lys
which one answer best describes the C-terminal amino acid in the structure below
Pro
which reactant is needed for the synthesis of alanine using the streaker synthesis
acetaldehyde
Given the pKa data below, select the one statement that is most true
arginine has a net positive charge in pH5.4 buffer
which one answer is the abbreviated formula of the peptide shown below
asp-ala-ser-lys
Given the pKa data below, select the one statement that is most true
asparagine has net neutral charge in pH 5.4 buffer
the purpose of treating a protein with DTT is to
break disulfide bridges
which is not true about N-ethylaniline
cannot form hydrogen bonds
which one is not an endopeptidase
carboxypeptidase B
which one most likely cannot be used to determine the N-terminal amino acid in a peptide
chymotrypsin
Select the one statement that is most true about the peptide below
complete hydrolysis produces three tyrosine residues
The purpose of treating a protein with ammonium sulfate is to
denature by destroying any nonbonding interactions
select the one statement that is most true about the peptide below
digestion with carboxypeptidase A will produce glycine
Humans are able to synthesize only 10 of the 20 common amino acids necessary for protein synthesis. The remaining 10 are called ___ amino acids since they must be obtained from dietary sources
essential
which amino acid cannot be formed from this synthetic method
glycine
The structure of heroin is shown below. which one phrase is not true about this compound
major component of poppy pods
which amino acid cannot be formed from this synthetic method
proline
which reactant is needed for the synthesis of alanine using reductive lamination?
pyretic acid
which must have a higher boiling point than N,N-dimethyl-2-hexanamine
secondary amine with higher mol. weight
which one answer most accurately describes the structures
structure 1 is a nitrosonium ion
which one answer most accurately describes the structures
structure 3 is a diazonium ion
which one answer best describes the product that forms when the compound below is treated with ammonia
tBoc-Lys
Which one answer best describes the structure shown below
tBoc-Phe-Pro
The compound below is classified as a(n)
tertiary amine
which is true about the basicity of the nitrogen lone pairs in the compound below
the alkyl amine is more basic than the imine
which one answer most accurately lists the reaction steps for the transformation
1.hydrogenation 2.diazotization 3. sandmeyer
What is the product of the reaction shown below
A
What is the product of the reaction shown below?
A
what is the major product of the reaction sequence below
A
which of the compounds below is a reagent used to identify the N-terminal amino acid
A
The side chain of the amino acid histidine includes an imidazole ring. Which nitrogen in this ring is the most basic
A. Nb is more basic because the lone pairs on this nitrogen are not part of the aromatic system
Classify amines (1) and (2) below
A. 1) secondary and 2) tertiary
The structure of heroin is shown below. Which ONE phrase is NOT true about this compound
A. Major component of poppy pods
Choose the one answer (A-E) that best describes the reaction conditions that will most likely produce the psychedelic designer drug, cimbi-5
A. Reagent Set #1 is a catalytic acid +heat and Reagent Set #2 is Na(CN)BH3 reduction
Which of the following is most true about the nucleophilicity and basicity of amines
A. amides are less basic than amines due to resonance
Which of the following pairs of amino acids could you most easily separate using gel electrophoresis in a pH=8.5 buffer?
A. histidine and arginine
Choose the one answer that best lists the missing structures made during the synthetic route shown below
B
Given the pKa data in the chart below, choose the one structure that is drawn correctly for a naturally occurring amino acid when the pH =pl
B
What is the missing product of the following Edman degradation
B
What is the parodic of the reaction sequence shown below?
B
What is the product of the following reaction?
B
What is the product of the reaction sequence shown below
B
What is the product of the reaction sequence shown below?
B
Which of the following amines is NOT water soluble
B
what is the product of the reaction sequence shown below
B
What are the best reagents to use for the following deprotection
B 1)H2O, NaOH, Heat 2)H3O+
Choose the one reaction condition (A-E) that will produce the product shown most efficiently
C. Diphenylamine +excess bromoethane with potassium carbonate
Choose the one answer that best completes the following statement "The structure of L-lysine looks like.."
D
Choose the one answer that best describes the process and provides the structure of the major product
D
Choose the one answer that best describes/compares the basicity of pyridine and 2,6-lutidine
D
Choose the one answer that lists the structures of the best reactant and the reagent needed to form the product
D
What is the missing product of the following reaction
D
Which of the following most accurately describes the following compounds
D
which of the compounds below is the zwitterion form of alanine
D
In an ion exchange column with sulfonate polystyrene beads, which is the correct order of elution for the following amino acids in a pH=6 buffer
D. Glu,Ser,His
All of the following are true about the compounds except
D. compound 2 is the PTH of Gin
All of the following are important things to know for exam 3 EXCEPT
D. knowles asymmetric hydrogenation involves the anti-addition of hydrogen gas to a (z)-enamido acid
What is the IUPAC name of this amine
D. 2-Chloro-5-ethylaniline
Which reactant is needed for the synthesis of alanine using the streaker synthesis
D. Acetaldehyde
All of the following are true about protein structure EXCEPT
D. All proteins have a quaternary structure
Which of the following amino acids is polar neutral?
D. Lys
Choose the one name (A-E) that represents an amine that is water Insoluble and will form an ammonium salt of a tertiary amine when placed in acid
D. N,N-dimethyl-2-hexanamine
Which of the following is the reactant and major product of Hofmann Elimination
D. Reactant: Amine Product: Hofmann Alkene
What is always the reactant and product of Knowles asymmetric hydrogenation?
E. Reactant: (Z)-Enamido Acid Product: S-Amino Acid Enantiomer
