Question 1

What is the correct IUPAC name for the following compound: a five-membered ring with a double bond between carbons 1 and 2, and a bromine substituent at carbon 4?

Accepted Answer

4-bromocyclopent-1-ene

Question 2

Ozonolysis of a six-membered ring alkene yields two molecules of butanal. What is the most likely structure of the original compound?

Accepted Answer

Cyclohex-3-ene-1,4-diol

Question 3

Which of the following best describes the reaction of an alkene with $$ \mathrm{Cl_2$}  in $$water?

Accepted Answer

Regioselective and stereoselective, but not stereospecific

Question 4

Which of the following is the correct resonance hybrid for the acetate ion ($$ \mathrm{CH_3COO^-} $$)?

Accepted Answer

Both oxygens share a negative charge equally, with delocalized pi electrons

Question 5

Which of the following reagents would you use to convert 1-butyne to trans-2-butene?

Accepted Answer

$$ \mathrm{Na/NH_3$ (l)} $$

Question 6

Which of the following best explains why the addition of $$ \mathrm{HBr}  to 2-$$methylpropene is regioselective?

Accepted Answer

The more stable carbocation intermediate forms, leading to Markovnikov addition

Question 7

Which of the following compounds is aromatic?

Accepted Answer

Benzene ($$ \mathrm{C_6H_6} )$$

Question 8

Which of the following is the correct Frost circle diagram for cyclopentadienyl anion ($$ \mathrm{C_5H_5^-} $$)?

Accepted Answer

A pentagon inscribed in a circle with 2 electrons in each of the three lowest energy levels

Question 9

Rank the following groups in order of reactivity with $$ \mathrm{HBr} $$: A (alkene), B (alkyne), C (alkane), D (aromatic ring).

Accepted Answer

A \u003e B \u003e C \u003e D

Question 10

Which of the following is the stronger acid?

Accepted Answer

p-nitrophenol ($$ \mathrm{NO_2$} $$ group on phenol)

Question 11

Which of the following best describes the mechanism of halogenation of alkenes?

Accepted Answer

Formation of a cyclic halonium ion intermediate followed by anti addition

Question 12

Which of the following is a resonance contributor for the nitro group ($$ \mathrm{NO_2$^-} $$)?

Accepted Answer

One oxygen has a negative charge, the other is double bonded to nitrogen

Question 13

Which of the following best describes the product of hydroboration-oxidation of 1-butene?

Accepted Answer

1-butanol with anti-Markovnikov addition

Question 14

Which of the following is true about the reaction of $$ \mathrm{H_2SO_4} $$ and water with an alkene?

Accepted Answer

It is regioselective and follows Markovnikov's rule

Question 15

Which of the following is the correct order of acidity for the following: phenol, ethanol, acetic acid?

Accepted Answer

Acetic acid \u003e phenol \u003e ethanol

Question 16

Which of the following is a correct resonance structure for the allyl cation ($$ \mathrm{C_3H_5^+} $$)?

Accepted Answer

The positive charge is delocalized over the terminal carbons

Question 17

Which of the following is the product of the reaction of 1-butyne with $$ \mathrm{HBr}  (1 $$equivalent)?

Accepted Answer

2-bromobut-1-ene

Question 18

Which of the following is antiaromatic?

Accepted Answer

Cyclobutadiene

Question 19

Which of the following is the correct product for the hydration of 2-methylpropene with $$ \mathrm{H_2SO_4} $$ and water?

Accepted Answer

2-methyl-2-propanol

Organic Chemistry Worksheet Study Guidance – Naming, Mechanisms, Reactivity, and Synthesis

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