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ACS Practice Exam for Organic I and II

June 4, 2021 by orgoly

Organic Chemistry
ACS Practice Exam for Organic I and II

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Categories

Acids and Bases 0%
Electrophilic Additions 0%
Electrophilic and Nucleophilic Aromatic Substitution 0%
Enols and Enolate Ion Reactions 0%
Nomenclature 0%
Nucleophilic Addition at Carbonyl Groups 0%
Nucleophilic Substitution at Carbonyl Groups 0%
Nucleophilic Substitutions and Eliminations 0%
Oxidations and Reductions 0%
Radical Substitutions and Additions 0%
Spectroscopy 0%
Stereoisomerism 0%
Structure, Hybridization, Resonance, Aromaticity 0%
Synthesis and Analysis 0%
Synthesis and Qualitative Analysis 0%

Question 1 of 34

1. Question

Category: Nomenclature

Which of the following molecules contains alcohol, ester and ketone functional groups?

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Question 2 of 34

2. Question

Category: Nomenclature

What is the IUPAC name of the following compound?

3-chloro-4-hexanone
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4-chloro-3-hexanone
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4-chlorohexanone
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4-chloro-3-oxohexane
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Question 3 of 34

3. Question

Category: Structure, Hybridization, Resonance, Aromaticity

Which of the following structures has 8 π electrons?

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Question 4 of 34

4. Question

Category: Structure, Hybridization, Resonance, Aromaticity

What is the hybridization of the orbital containing the unshared pair of electrons in the following molecule?

sp
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sp²
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sp³
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sp³d²
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Question 5 of 34

5. Question

Category: Acids and Bases

Arrange the following compounds in order from the most acidic to the least acidic.

IV > II > I > III
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III > I > II > IV
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II > IV > I > III
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I > IV > II > III
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Question 6 of 34

6. Question

Category: Acids and Bases

Which of the following protons would have the lowest pK_a value?

1
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Question 7 of 34

7. Question

Category: Acids and Bases

Which of the following carboxylates is the strongest base?

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Question 8 of 34

8. Question

Category: Stereoisomerism

What is the stereochemical relationship between the salts formed when racemic lactic acid reacts with (R)-1-phenylethylamine?

diastereomers
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enantiomers
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constitutional isomers
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racemates
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Question 9 of 34

9. Question

Category: Stereoisomerism

What is the total number of possible stereoisomers for 2-bromo-3-chlorobutane?

2
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Question 10 of 34

10. Question

Category: Stereoisomerism

Which molecule is the enantiomer of the following?

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Question 11 of 34

11. Question

Category: Nucleophilic Substitutions and Eliminations

Why would HCl be an inappropriate catalyst to use for the acid-catalyzed dehydration of a tertiary alcohol?

HCl is too weak of an acid to protonate the alcohol.
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The conjugate base of HCl is a good nucleophile and would yield the substitution product.
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HCl is too strong of an acid to turn the hydroxyl group into a good leaving group.
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HCl is too strong of an acid and would cause the carbocation to rearrange.
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Question 12 of 34

12. Question

Category: Nucleophilic Substitutions and Eliminations

What is the major product of the following reaction?

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Question 13 of 34

13. Question

Category: Electrophilic Additions

What is the major product of the following reaction?

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Question 14 of 34

14. Question

Category: Electrophilic Additions

What is the major product of the following reaction?

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Question 15 of 34

15. Question

Category: Nucleophilic Addition at Carbonyl Groups

Which of the following reagents would best accomplish the reaction shown?

CH₃Li
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CH₃MgBr
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(CH₃)₂CuLi
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LiAlH₄
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Question 16 of 34

16. Question

Category: Nucleophilic Addition at Carbonyl Groups

What is the major product of the following sequence of reactions?

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Question 17 of 34

17. Question

Category: Nucleophilic Substitution at Carbonyl Groups

Which reagent would best accomplish the following reaction?

SOCl₂
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Cl₂, hν
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HCl
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NCS (N-chlorosuccinimide)
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Question 18 of 34

18. Question

Category: Nucleophilic Substitution at Carbonyl Groups

Which of the following compounds would be hydrolyzed the most slowly in aqueous KOH?

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Question 19 of 34

19. Question

Category: Enols and Enolate Ion Reactions

Which of the following compounds is the product of an aldol reaction?

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Question 20 of 34

20. Question

Category: Spectroscopy

Which structure is most consistent with the following mass spectrum? Tap/click and drag to zoom in. Double tap/click to reset zoom. Pinch/scroll to scale.

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Question 21 of 34

21. Question

Category: Enols and Enolate Ion Reactions

What is the major product of the following sequence of reactions?

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Question 22 of 34

22. Question

Category: Electrophilic and Nucleophilic Aromatic Substitution

What is the major product of the following sequence of reactions?

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Question 23 of 34

23. Question

Category: Electrophilic and Nucleophilic Aromatic Substitution

What type of reaction is shown?

electrophilic substitution
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nucleophilic substitution
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electrophilic addition
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nucleophilic addition
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Question 24 of 34

24. Question

Category: Radical Substitutions and Additions

Which reagent would best accomplish the following reaction?

HBr, peroxides
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Br₂, hν
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HBr
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NBS (N-bromosuccinimide), hν

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Question 25 of 34

25. Question

Category: Radical Substitutions and Additions

Which of the following positions is the most reactive toward a bromine radical?

1
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Question 26 of 34

26. Question

Category: Oxidations and Reductions

Ozonolysis of which compound would yield the following products?

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Question 27 of 34

27. Question

Category: Oxidations and Reductions

Which reagent would best accomplish the following reaction?

NaBH₄
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LiAlH₄
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H₂NNH₂, KOH
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diisobutylaluminum hydride (DiBAL)
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Question 28 of 34

28. Question

Category: Spectroscopy

Which structure is consistent with the following ¹H NMR spectrum? Tap/click and drag to zoom in. Double tap/click to reset zoom. Pinch/scroll to scale.

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Question 29 of 34

29. Question

Category: Spectroscopy

Which compound will have the lowest frequency (in cm^-1) absorption by infrared spectroscopy for the carbonyl (C=O) group?

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Question 30 of 34

30. Question

Category: Synthesis and Analysis

Which sequence of reagents would best accomplish the following conversion?

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Question 31 of 34

31. Question

Category: Synthesis and Analysis

An optically inactive ketone undergoes reduction by sodium borohydride (NaBH₄) to give a racemic mixture of products. Which of the following compounds is consistent with this?

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Question 32 of 34

32. Question

Category: Spectroscopy

Which structure is consistent with the following IR spectrum? Tap/click and drag to zoom in. Double tap/click to reset zoom. Pinch/scroll to scale.

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Question 33 of 34

33. Question

Category: Spectroscopy

Which structure is most consistent with the following ¹³C NMR spectrum? Tap/click and drag to zoom in. Double tap/click to reset zoom. Pinch/scroll to scale.

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Question 34 of 34

34. Question

Category: Synthesis and Qualitative Analysis

What is the major product of the reaction sequence shown?

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