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Basic Organic Chemistry Trivia Quiz

This requires a good amount of education in organic chemistry, but any second semester student should be able to answer the following questions. They are fairly simple, not meant to be tricky or difficult in any way. Good luck!

A multiple-choice quiz by karen_rx. Estimated time: 6 mins.

Author
karen_rx

Time
6 mins

Type
Multiple Choice

Quiz #
69,471

Updated
Dec 03 21

# Qns
10

Difficulty
Difficult

Avg Score
4 / 10

Plays
5833

One at a Time - Single Page - Timed Game

Question 1 of 10

1. Which of the following types of reactions involves R-X, Li, CuI, and R'-X? Hint

Clemmenson Reduction

Corey-Posner , Whitesides-House synthesis

Friedel-Crafts Alkylation

Grignard synthesis

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Question 2 of 10

2. In the type of reaction involving R-X, Li, CuI, and R'-X?; R'-X must NOT be which of the following? Hint

Tertiary

Methyl

Primary

Secondary cycloalkyl

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Question 3 of 10

3. Grignard reagents react with ketones to form which of the following? Hint

Tertiary alcohols

Secondary alcohols

Primary alcohols

Carboxylic acids

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Question 4 of 10

4. Which of the following is a Huckel number? Hint

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Question 5 of 10

5. Which of the following are reagents used in the nitration of benzene? Hint

Conc. HNO3 and conc. H2SO4

Ammonia

Dilute solutions of NO3 and H2SO4

Concentrated NO3

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Question 6 of 10

6. Which of the following is NOT associated with oxidation? Hint

Hot KMnO4

PCC

LiAlH4

Jones Reagent

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Question 7 of 10

7. Which of the following will reduce an aldehyde but not a carboxylic acid? Hint

LiAlH4

NaBH4

H2, Pt catalyst

PCC

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Question 8 of 10

8. If branching of the side chain in the product is a problem in Friedel-Crafts alkylation, how can a product with an unbranched side chain be reached? Hint

It can't--the more stable carbocation cannot be avoided

Use Cl2 instead of AlCl3

Treat the product with a strong acid

Friedel-Crafts acylation followed by Clemmenson reduction

NEXT>

Question 9 of 10

9. A methyl group on benzene is considered which of the following? Hint

Meta director, deactivating

Ortho-para director, deactivating

Ortho-para director, activating

Meta director, activating

NEXT>

Question 10 of 10

10. When an alcohol is exposed to an acid, what is the first thing that always happens? Hint

It becomes a diol

An acid-base reaction

Protonation of the hydroxyl group

A double bond forms

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Quiz Answer Key and Fun Facts

1. Which of the following types of reactions involves R-X, Li, CuI, and R'-X?

Answer: Corey-Posner , Whitesides-House synthesis

If you picked Grignard synthesis, close, but not exactly. Grignard syntheses make {alcohols;} Corey-Posner syntheses make new carbon-carbon bonds.

2. In the type of reaction involving R-X, Li, CuI, and {R'-X?;} R'-X must NOT be which of the following?

Answer: Tertiary

By the way, I was nice and didn't throw in secondary by itself without the cycloalkyl part. :)

3. Grignard reagents react with ketones to form which of the following?

Answer: Tertiary alcohols

A ketone already has two R groups, the Grignard adds a third, and protonation removes the MgX to form a hydroxyl group.

4. Which of the following is a Huckel number?

Answer: 10

The Huckel rule is: 4n + 2. 8-2=6, 12-2=10, and 16-2=14, none of which can be divided by four to produce a whole number. {10-2=8;} 8 divided by 4 is {2;} therefore, 10 is a Huckel number.

5. Which of the following are reagents used in the nitration of benzene?

Answer: Conc. HNO3 and conc. H2SO4

The sulfuric acid aids in production of the electrophile, O=N(+)=O (sorry, hard to show structure here). The acids must be concentrated, or the reaction will not work!

6. Which of the following is NOT associated with oxidation?

Answer: LiAlH4

LiAlH4 (LAH) is a reducing agent, the others all oxidize alcohols to carbonyl compounds.

7. Which of the following will reduce an aldehyde but not a carboxylic acid?

Answer: NaBH4

LAH will reduce the aldehyde AND the carboxylic acid, H2, Pt catalyst will reduce neither functional group, and PCC is an oxidizing agent, not a reducing agent.

8. If branching of the side chain in the product is a problem in Friedel-Crafts alkylation, how can a product with an unbranched side chain be reached?

Answer: Friedel-Crafts acylation followed by Clemmenson reduction

Ok, this one was obvious--none of the incorrect answers make any sense. (While the tertiary carbocation cannot be avoided in Friedel-Crafts alkylation, there is definitely still a way to synthesize the desired product--never give up!)

9. A methyl group on benzene is considered which of the following?

Answer: Ortho-para director, activating

The methyl group directs substituents to either the ortho (1,2) or para (1,4) position, not the meta (1,3), which is generally less stable. The methyl group also causes the compound to be more reactive than benzene itself, so it is an activating group.

10. When an alcohol is exposed to an acid, what is the first thing that always happens?

Answer: Protonation of the hydroxyl group

Protonation is always the first step because OH is a poor leaving group, and (+)OH2 is a good leaving group. The elimination can only occur after protonation, thus forming the double bond.

Source: Author karen_rx

This quiz was reviewed by FunTrivia editor crisw before going online.
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