Organic Chemistry Standardized Test & Common Abbreviations Excel Worksheet

 

Organic Chemistry 1 “Multiple Choice Organic Thing” (MCOT) Fall, 2020

 

A note before we start

I worked hard to make this assessment – about a full workday, over a weekend, while my family and I were trying to recover from COVID. I did it so that you would have a way to test your skills and get an idea how you were doing in your effort to learn organic chemistry. As you know, this is an ungraded class, and this test is a self-assessment. You have the right to argue for whatever grade you believe you deserve regardless of your score on this test.

Please do not upload this test to websites like Chegg. I ask you as a personal favor. If you do, a lot of work on my part will have been wasted. Thank you so much.

Dr. Marshall

Instructions

Set aside 2 hours in a quiet space when you think you will be un-interrupted. Take this test using only the knowledge you’re carrying around in your head and the data sheet provided. Work out the problems on scratch paper as you go, and write down your answers. When you are finished with the test, type your answers into the Excel answer sheet provided and upload the answer sheet to Blackboard.

Data Sheet of Common Abbreviations

Structures Reagents Solvents

ROOR

peroxide

O

N

Lindlar’s catalyst

Pd with Pb,

sometimes

also quinoline/CaCO

3

Me

2

S

dimethyl sulfide

HOAc/OAc

acetic acid or acetate

O

OH

O

O

pyridine

O

O

Cl

O

H

mCPBA

meta-

chloroperoxybenzoic acid

N

O

O

Br

NBS

N-bromosuccinimide

S

O

DMSO

dimethylsulfoxide

O

acetone

S

O

O

X

tosyl group (Ts-X)

X=Cl is tosyl chloride (TsCl)

X-OR is a tosylate (R-OTs)

O

R

tert-butoxide group

t-BuOR/t-BuO

(

)

O

N

H

O

DMF

dimethylformamide

THF

tetrahydrofuran

 

  1. What is the IUPAC (chemical) name for the compound shown?

 

 

      1. 3-methyl-5-hexene
      2. 4-methyl-1-hexene
      3. 3-methyl-2-hexene
      4. 2-methyl-5-hexene

 

  1. Which structure represents 2-cyclopropyl-3-methyloctane?

a b c d

 

  1. What is the IUPAC name for the compound shown?

 

HO

Cl

      1. 1-chloro-4-butanol
      2. 2-chloro-4-butanol
      3. 3-chloro-1-butanol
      4. 4-chloro-1-butanol

 

  1. What is the IUPAC name for the compound shown?

 

Br

Br

      1. cis-1,3-dibromocyclohexane
      2. trans-1,3-dibromocyclohexane
      3. cis-1,4-dibromocyclohexane
      4. trans-1,4-dibromocyclohexane

 

  1. What is the best IUPAC name for the compound shown? Cl

 

Cl

      1. 2,3-dichloro-4,5-dimethyl-(2E,4E)-hepta-2,4-diene
      2. 2,3-dichloro-4,5-dimethyl-(2E,4Z)-hepta-2,4-diene
      3. 2,3-dichloro-4,5-dimethyl-(2Z,4E)-hepta-2,4-diene
      4. 2,3-dichloro-4,5-dimethyl-(2Z,4Z)-hepta-2,4-diene

 

  1. What are functional groups present in the natural compond shown, α-terpineol?

OH

 

      1. Aromatic ring, secondary alcohol, alkene
      2. Aromatic ring, tertiary alcohol, alkene
      3. Secondary alcohol, alkene
      4. Tertiary alcohol, alkene
  1. A compound with the formula C5H12O may contain which of the following functional groups?
      1. ketone
      2. alkene
      3. ether
      4. ester
  2. What is the geometry of the boron atom in sodium borohydride, NaBH4? a. trigonal planar
      1. linear
      2. trigonal bipyramidal
      3. tetrahedral
  3. For the nitrogen and oxygen in the compound shown, what are the formal charges? All lone pairs are shown, but the formal charges are not written.

 

N

O

      1. N is 0, O is -1
      2. N is -1, O is +1
      3. N is +1, O is 0
      4. N is +1, O is -1
  1. Which functional group has the largest dipole moment?
      1. alkene
      2. ether
      3. ketone
      4. chloroalkane
  2. Which of the radicals shown is the most stable?
    1. b c

d

 

  1. Which of the structures shown is not a resonance structure of the others?
    1. a

O

H

O

H

O

H

O

H

b

c

d

 

13.

 

Which is the lowest energy conformation of trans-1-chloro-2-ethylcyclohexane?

Cl

Cl

Cl

Cl

b

c

d

 

 

  1. For the structures shown, which is the correct order of boiling points? iH iiOH iii

O

    1. i < iii < ii
    2. ii < i < iii
    3. iii < i < ii
    4. ii < iii < i

 

  1. Which of the alkenes shown will react most exothermically with hydrogen and Pd catalyst?

a

b

c

d

 

16.

 

Which point on the energy diagram shown represents the Newman projection in the figure?

 

word image 3367

  1. Which of the following arrow symbols means the same thing as “These two structures are resonance forms of each other?”
    1. c d

b

 

  1. 2-bromopentane reacts with methanol under heat to produce 2-methoxypentane. What is the overall order of this reaction?
      1. zeroth order
      2. first order
      3. second order
      4. cannot be predicted from the information given
  2. What is the degree of unsaturation for the structure shown?

 

      1. 0
      2. 1
      3. 2
      4. 3
  1. Which is the most acidic hydrogen in the amino acid shown? d O

b H2N

c

OH

HO

a

 

  1. Which of the following structures does not react as a Lewis acid?
      1. CH3+
      2. BH3
      3. NH3
      4. CH3CH2Cl
  2. Which of the structures shown is the strongest Bronsted-Lowry acid?

O O O O abcd

OHOH ClOHOH

F

  1. What is the correct R/S labeling for the stereocenter(s) in the molecule represented by the Newman projection shown?

Cl

ClCH3

H3CCH3

H

      1. R
      2. S
      3. (2R,3R)
      4. (2S,3S)
  1. The correct term for this pair of structures is:

CH3 CH3

HOH HOH

HOH HOH

CH3 CH3

      1. diastereomers
      2. enantiomers
      3. constitutional isomers
      4. identical compounds
  1. In the sex hormone shown, how many stereocenters are present?

OH

HO

 

      1. 2
      2. 3
      3. 4
      4. 5
  1. This molecule contains two stereocenters. If the IUPAC numbering of the ring system is as shown, what are the R/S configurations of those stereocenters?

OH

5

6

O 2

NH

3

4

1

 

      1. (2R,4R)
      2. (2R,4S)
      3. (2S,4R)
      4. (2R,4R)
  1. Which compounds will rotate plane-polarized light?

OF

F

OH

i ii iii iv

 

        1. i, ii, and iv
        2. ii, ii, and iv
        3. i, iii, and iv
        4. i, ii, and iii

 

  1. At room temperature, the structure below is:

F

F

 

        1. achiral
        2. a cis cyclohexane
        3. chiral
        4. a meso compound
  1. What is the correct description of the two structures shown?

H

Br

Br

H

        1. They are enantiomers.
        2. They are diastereomers.
        3. They are constitutional isomers.
        4. They are the same compound.
  1. Which reaction would produce a meso product?

 

Br HCl

2

      1. c

D

BH

3

      1. d

2

Pt

 

 

  1. In the most favored conformation of trans-1,3-diethylcyclohexane, how many axial H atoms are present? a. 2
        1. 3
        2. 4
        3. 5

 

 

  1. Which of the structures shown will react fastest in an SN1 reaction?

Br BrBr abc

d

Br

 

  1. Which factor does not directly effect the rate at which an alkyl halide reacts in an SN2 step?
      1. Stability of the carbocation it forms
      2. The solvent in which the reaction occurs
      3. The strength of the nucleophile
      4. The steric hindrance of the alkyl halide
  2. Which of these reactants would react the fastest in an SN2 reaction?
      1. CH3CH2Cl
      2. CH3CH2OTs
      3. CH3CH2OH
      4. CH3CH2CN
  3. Which of the molecules shown would react well in both an SN1 and SN2 reaction?

 

word image 1183 a

 

a

CN CN a d

 

    1. d

 

 

  1. Which of the H atoms will be removed in an elimination reaction using t-BuOK and t-BuOH as solvent?

Hb

HdCH3

Cl

Ha

CH

3

Hc

  1. Which of the following sets of reagents will perform the reaction shown, specifically making the trans alkene product?

 

?

    1. H2, Pd on C
    2. Na metal, NH3, cold
    3. H2O, H2SO4
    4. H2, Lindlar’s catalyst
  1. Which is the major organic product (along with its enantiomer, where applicable) of the reaction shown?

word image 1184 O, KOH

a OH

OH

a d

 

OH

a

 

  1. An unknown compound undergoes ozonolysis. Which of the options shown could possibly be the identity of the unknown compound?

 

O

H

O

a

b

c

d

1

.

O

3

,

very cold

2

. Zn

?

  1. Which set of reagents will perform the reaction shown, making the product shown?

OH

 

    1. H3O+
    2. BH3, THF 2. H2O2, H2O, OH-
    3. OsO4 followed by a reducing agent
    4. Conc. H2SO4
  1. What is the most likely product of the alkyl halide shown reacting under the indicated conditions?

Br

ONa

OH

O

O

a

b

c

d

 

  1. What is the mechanism of the reaction shown?

H3PO4

OH

(phosphoric acid)

 

    1. E1
    2. SN1
    3. E2
    4. SN2
  1. What is the IUPAC name of the product of the radical reaction shown?

Br

2

hv

 

    1. 1-bromo-2-methylcyclohexane
    2. (bromomethyl)cyclohexane
    3. 1-bromo-3-methylcyclohexane
    4. 1-bromo-1-methylcyclohexane
  1. Propene reacts with HBr in the presence of a peroxide. Which of the steps shown is a propagation step in this reaction?

a

+ HBr

Br

Br

Br

2

RO

 

b+ Br

c+ Br d ROOR

  1. Which compound has a C-H bond with the lowest bond dissociation energy?
    1. Methane
    2. Propane
    3. 2-methylpropane
    4. Butane
  2. What reagent will perform the reaction shown?

O

 

    1. OsO4
    2. NaClO
    3. CrO3
    4. mCPBA
  1. Which reagent will perform the reaction shown?

OH OH

    1. H2, Pt
    2. NaOH, H2O
    3. LiAlH4
    4. HCl
  1. Which phrase describes a reasonable retrosynthesis of the molecule above, as shown?

 

SH

    1. Anti-Markovnikov addition of HBr, then nucleophilic substitution with SH-
    2. Nucleophilic substitution with SH-, then anti-Markovnikov addition of HBr
    3. Markovnikov addition of HBr, then nucleophilic substitution with SH-
    4. Nucleophilic substitution with SH-, then anti-Markovnikov addition of HBr 56. What is the final product of the four-step synthetic sequence shown?

BH

3

H

2

O

2

,

H

2

O/OH

NaH

THF

CH

3

I

?

OH

O

HO

O

a

b

c

d

 

  1. Toluene, a common paint stripper and solvent, is a drug of abuse by inhalation or “huffing.” It is metabolized in the body by oxidation. Which of the compounds shown could not have been produced from toluene by oxidation?

toluene

O H

    1. OH b OH c O d

 

  1. Taking stereochemistry into account, what is the most likely major product of the addition reaction step between cyanide nucleophile and the epoxide shown?

acd

O

C

N

O

CN

CN

O

b

O

CN

O

CN

 

  1. Which is the most likely major organic product of the synthetic sequence below?
        1. NaNH2
        2. CH3I
        3. H2, Lindlar’s cat.
    1. b c d

 

  1. For a certain chemical reaction, researchers have determined that starting material X is converted to a product Z by formation of a high-energy reactive intermediate Y. What point on the diagram represents the structure of Y?

word image 3368

  1. For the reaction above, what point on the diagram represents the transition step of the rate-limiting step?
  2. A section of a polymer chain is shown. What monomer could give the polymer shown by radical polymerization?
    1. d

C

C

C

C

N

N

N

N

b

c

CN CN CN CN CN

  1. The polymer above can be formed by anionic polymerization as well as radical polymerization, where a nucleophile attacks a monomer and generates a carbanion nucleophile on it, which starts the growth of a polymer chain. Why is this possible in this case?
      1. The bond between the double bond and the CN group is very weak.
      2. The CN group is an alkyl group, which stabilizes the carbocation.
      3. The CN is sterically bulky, which helps make the intermediate more stable.
      4. The CN stabilizes the intermediate by resonance.
  2. What is the hybridization of the C atom in the CN group in the polymer question above? a. sp
      1. sp2
      2. sp3
      3. sp3d
  3. For which molecule could this be the mass spectrum?

 

Cl

Br

S

OH

OH

a

b

c

d

 

word image 3369

  1. Which of the structures shown has exactly 2 peaks in its 13C NMR spectrum?

OH Br OH

a b Br c d

OH

  1. Which molecule could give this 1H NMR spectrum?

 

word image 3370

      1. Bromoethane
      2. 1-bromopropane
      3. 2-bromopropane
      4. 1-bromobutane
  1. IR and 1H NMR spectra for a molecule are given below. Identify the molecule.

 

 

word image 3371 word image 3372

    1. propane
    2. 1-propanol
    3. butanone
    4. methyl ethyl ether
  1. Which of the structures shown could give rise to the following NMR spectrum?

 

OH

OH

O

OH

O

OH

OH

O

HO

OH

O

a

b

c

d

 

word image 3373

  1. Which of the compounds shown could give the IR spectrum below?

 

Br

OH

O

OH

a

b

c

d

 

word image 3374

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