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CHM 1321...

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CHM 1321 B – Organic Chemistry I

Question 1 (2 points) Which of the following statements about this reaction are true?

Question 1 options: Hydrogen is more electronegative than boron The C-H bond forms faster than the C-C bond breaks The reaction is concerted The intermediate ion is stabilized by hyperconjugation The reaction produces the Markovnikov product The regiochemistry is controlled by the energies of the transition states

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CHM 1321 B – Organic Chemistry I

Question 2 (1 point)

Identify which of the following statements describing the reaction are true.

Question 2 options: The reaction forms a mixture of products FeBr3 accelerates the reaction by acting as a Lewis base catalyst The arenium ion has 3 resonance forms Proton removal is rate determining The reaction forms the meta isomer This bromination would be faster if chlorobenzene was used instead of toluene

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CHM 1321 B – Organic Chemistry I

Question 3 (2 points)

Which of the following reactions are likely to fail? Select all that apply.

Question 3 options: A B C D

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CHM 1321 B – Organic Chemistry I

Question 4 (1 point) Which of the following resonance forms contribute to the ion formed during the following reaction? (select all that apply)

Question 4 options:

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CHM 1321 B – Organic Chemistry I

Question 5 (1 point) What is the product of the following reaction sequence?

Question 5 options:

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CHM 1321 B – Organic Chemistry I

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CHM 1321 B – Organic Chemistry I

Question 6 (1 point) What is the product of the following sequence?

Question 6 options:

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CHM 1321 B – Organic Chemistry I

Question 7 (1 point)

Which of the illustrated structures is the enantiomer of the following:

Question 7 options: A B C D E F 8

CHM 1321 B – Organic Chemistry I

Question 8 (1 point) This reaction is a common way to create carbon-carbon bonds.

Which of the following shows the reverse reaction of the one shown above? Question 8 options:

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CHM 1321 B – Organic Chemistry I

Question 9 (1 point) Select the reaction components that are necessary for the following reaction to succeed. Select all that apply.

Question 9 options: H2O H2SO4 Br2 SO3 CuCl2 HNO3 H3PO4 Cl2 AlBr3 FeCl3 AlCl3 FeBr3

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CHM 1321 B – Organic Chemistry I

Question 10 (2 points) Match each of the following reactions to the correct product Question 10 options:

product 6

product 3

product 1

product 5

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CHM 1321 B – Organic Chemistry I

1.

2.

3.

4.

5.

6.

7.

8.

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CHM 1321 B – Organic Chemistry I

Question 11 (1 point) Identify the major product of the following reaction (select all that apply)

Question 11 options:

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CHM 1321 B – Organic Chemistry I

Question 12 (1 point) Select the reaction components that are necessary for the following reaction to succeed. Select all that apply.

Question 12 options: H3PO4 Cl2 HNO3 Br2 FeBr3 AlBr3 SO3 FeCl3 H2O AlCl3 CuCl2 H2SO4

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CHM 1321 B – Organic Chemistry I

Question 13 (2 points) Which of the following solvents should not be used for Grignard reactions? Select all that apply. Question 13 options: isopropanol ethyl acetate 2-propanone cyclohexane diethyl ether

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CHM 1321 B – Organic Chemistry I

Question 14 (1 point) What is the correct line structure of the following?

Question 14 options:

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CHM 1321 B – Organic Chemistry I

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CHM 1321 B – Organic Chemistry I

Question 15 (1 point) The following reaction was not seen in class, but is analogous to other electrophilic aromatic substitutions. Identify the major product(s) of this reaction. Select all that apply.

Question 15 options:

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CHM 1321 B – Organic Chemistry I

Question 16 (1 point) Predict the major product of the following synthetic sequence.

Question 16 options:

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CHM 1321 B – Organic Chemistry I

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CHM 1321 B – Organic Chemistry I

Question 17 (1 point) When the amino acid arginine, shown below, is dissolved in acid, which atom is protonated first?

Question 17 options: A B C D E

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CHM 1321 B – Organic Chemistry I

Question 18 (1 point) Predict the major product of the following reaction.

Question 18 options:

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CHM 1321 B – Organic Chemistry I

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CHM 1321 B – Organic Chemistry I

Question 19 (1 point) Which of the following molecules has 4 significant resonance forms? (select all that apply) Question 19 options:

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CHM 1321 B – Organic Chemistry I

Question 20 (1 point) Which of the following reactions occurs by a concerted mechanism?

Question 20 options: A B C D E 25

CHM 1321 B – Organic Chemistry I

Question 21 (1 point) The pKa of hydrogen (H2) is 35. The pKa of ammonia (NH3) is 38. What is the equilibrium constant for the following reaction?

Question 21 options: 1 3 -3 1000 0.001 10

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CHM 1321 B – Organic Chemistry I

Question 22 (1 point) This ion is formed during certain types of synthetic reactions. Which of the following represent good resonance structures?

Question 22 options:

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CHM 1321 B – Organic Chemistry I

Question 23 (1 point) What are the configurations of the indicated double bonds?

1: E 2: E 3: E

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CHM 1321 B – Organic Chemistry I

Question 24 (1 point) Which Newman projections depicts the molecule shown? (select all that apply)

Question 24 options:

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CHM 1321 B – Organic Chemistry I

Question 25 (1 point) Which of the following Grignard reagents would not be feasible to make and isolate. Select all that apply. Question 25 options:

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CHM 1321 B – Organic Chemistry I

Question 26 (1 point) Identify whether the following molecules are aromatic, antiaromatic or non-aromatic Question 26 options:

antiaromatic

aromatic

non-aromatic

aromatic

antiaromatic

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CHM 1321 B – Organic Chemistry I

Question 27 (1 point) Which of the following reactions will give a good yield of the product shown? (select all that apply) Question 27 options:

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CHM 1321 B – Organic Chemistry I

Question 28 (1 point) Which product is expected from the following reaction.

Question 28 options: A B C D E

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CHM 1321 B – Organic Chemistry I

Question 29 (1 point) Order the following conformers from most stable to least stable.

A>C>B

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CHM 1321 B – Organic Chemistry I

Question 30 (2 points) In which of the following acid/base reactions are the products favored. In other words, the equilibrium lies to the right. Select all that apply. Question 30 options:

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CHM 1321 B – Organic Chemistry I

Question 31 (1 point) Rank the following atoms from most basic to least basic.

C>A>B

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CHM 1321 B – Organic Chemistry I

Question 32 (1 point) A solution of 3.6 g of (+)-isobutanol in 8mL of water was placed in a 100 mm cell. Using the sodium D line, a rotation of +8.76° was found. Determine the specific rotation of (+)-isobutanol to one decimal place (do not include units).

+19.5 degrees

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CHM 1321 B – Organic Chemistry I

Question 33 (1 point) Which pair of reactants will give 2-phenylbutan-2-ol after aqueous workup? (select all that apply) Question 33 options:

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CHM 1321 B – Organic Chemistry I

Question 34 (1 point) Which of the illustrated products can be formed from the following reaction. Select all that apply.

Question 34 options:

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CHM 1321 B – Organic Chemistry I

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CHM 1321 B – Organic Chemistry I

Question 35 (1 point) What is the most likely location for electrophilic reactions to occur? Question 35 options:

B

B

A

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CHM 1321 B – Organic Chemistry I

Question 36 (1 point) What piece of laboratory equipment is used to prevent evaporation during reflux? Question 36 options:

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CHM 1321 B – Organic Chemistry I

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CHM 1321 B – Organic Chemistry I

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CHM 1321 B – Organic Chemistry I

Question 37 (2 points) What is the hybridization of the indicated atoms?

A: sp B: sp3 C: sp2 D: sp2

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CHM 1321 B – Organic Chemistry I

Question 38 (1 point) Which of the following molecules contain at least one atom with a non-zero formal charge? (select all that apply) Question 38 options:

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CHM 1321 B – Organic Chemistry I

Question 39 (1 point) Which of the following reactions produces a pair of diastereoisomers? Select all that apply. Question 39 options:

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CHM 1321 B – Organic Chemistry I

Question 40 (1 point) In the most stable conformation of the molecule shown below, how many substituents are in the axial position?

4

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CHM 1321 B – Organic Chemistry I

Question 41 (1 point) Rank the following resonance structures of ethyl acetate from best to worst Question 41 options:

third best

second best

best

fourth best (i.e. worst)

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CHM 1321 B – Organic Chemistry I

Question 42 (1 point) What site on the following molecule will react first?

3

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CHM 1321 B – Organic Chemistry I

Question 43 (1 point) Identify the stereochemical relationship between the following pairs of molecules Question 43 options:

diastereomers

diastereomers

constitutional isomers

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CHM 1321 B – Organic Chemistry I

same/identical

enantiomers

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CHM 1321 B – Organic Chemistry I

Question 44 (1 point) Identify the major product(s) of the following reaction. Select all that apply.

Question 44 options:

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CHM 1321 B – Organic Chemistry I

Question 45 (1 point) Assign priorities to the four substituents using the Cahn-Ingold-Prelog system

Priority 1: CO2H Priority 2: Phenyl Priority 3: CH3

Priority 4: H

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CHM 1321 B – Organic Chemistry I

Question 46 (1 point) Predict if the following reaction would work with the noted set of reagents.

A) B) C) D) E)

Would work using H2O/H3O_ Would work using Hg(OAc)2 then NaBH4 Would work using BH3 then H2O2 A+B None of the above

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CHM 1321 B – Organic Chemistry I

Question 47 (1 point) Assign priorities to the four substituents of the chirality centre using the Cahn-Ingold-Prelog system

Priority 1: OCH3 Priority 2: CH2NH2 Priority 3: CH2CH3

Priority 4: H

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CHM 1321 B – Organic Chemistry I

Question 48 (1 point) What are the configurations of the indicated stereocentres?

1: S

2: R 3: S

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CHM 1321 B – Organic Chemistry I

Question 49 (1 point) Which of the following reactions are appropriately described by the illustrated electron-pushing arrows? Select all that apply. Question 49 options:

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CHM 1321 B – Organic Chemistry I

Question 50 (1 point) Re-order the following steps to give the most efficient synthesis of the molecule below

1) SO3, H2SO4 2) (CH3)CCl, AlCl3 3) HNO3, H2SO4 4) Separate isomers

Step 1: (CH3)CCl, AlCl3 Step 2: HNO3, H2SO4 Step 3: Separate isomers Step 4: SO3, H2SO4

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CHM 1321 B – Organic Chemistry I

Question 51 (1 point) Which of the following illustrate well drawn electron-pushing arrows. Select all that apply.

A only

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CHM 1321 B – Organic Chemistry I

Question 52 (2 points) Which of the following are intermediates in the following reaction? (select all that apply)

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CHM 1321 B – Organic Chemistry I

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