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2024 Regional Championship chemistry Topic 25 Free

Organic reaction mechanisms: addition, substitution and elimination

Naming the distinct monochlorination products of a branched alkane · Sub-topic 1

REGIONAL CHAMPIONSHIP 2024

GOIL REGIONAL CHAMPIONSHIP — GRAND FINAL, BONO AHAFO ZONE

Sunyani Senior High School: 38 points (Winner)

St. James Seminary & Senior High School: 31 points

Kintampo Senior High School: 30 points

Our Lady of Mount Carmel Girls' Senior High School: 18 points


QUESTION

Give the name of one product formed when 2-methylbutane undergoes monochlorination.

ANSWER: 2-chloro-2-methylbutane, 1-chloro-2-methylbutane, 2-chloro-3-methylbutane, or 1-chloro-3-methylbutane (each accepted once)

SOLUTION:

2-Methylbutane, $(CH_3)_2CHCH_2CH_3$, has four chemically distinct hydrogen environments (the two equivalent C1/branch methyls count as one type), giving exactly four monochlorination products: chlorinating the tertiary C2–H gives 2-chloro-2-methylbutane; either terminal methyl on C2 gives 1-chloro-2-methylbutane; the C3 methylene gives 2-chloro-3-methylbutane; and the C4 methyl gives 1-chloro-3-methylbutane.


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PRACTICE QUESTIONS

1. QUESTION: Give the name of one product formed when propane undergoes monochlorination.

ANSWER: 1-chloropropane or 2-chloropropane

SOLUTION:

Propane has two kinds of hydrogen.


2. QUESTION: Give the name of one product formed when butane undergoes monochlorination.

ANSWER: 1-chlorobutane or 2-chlorobutane

SOLUTION:

Butane has primary and secondary hydrogens.


3. QUESTION: Give the name of one product formed when 2-methylpropane undergoes monochlorination.

ANSWER: 1-chloro-2-methylpropane or 2-chloro-2-methylpropane

SOLUTION:

2-methylpropane has primary and tertiary hydrogens.


4. QUESTION: Give the name of one product formed when pentane undergoes monochlorination.

ANSWER: 1-chloropentane, 2-chloropentane or 3-chloropentane

SOLUTION:

Pentane has three kinds of hydrogen.


5. QUESTION: Give the name of the product formed when 2,2-dimethylpropane undergoes monochlorination.

ANSWER: 1-chloro-2,2-dimethylpropane

SOLUTION:

All its hydrogens are equivalent, so only one product forms.


6. QUESTION: Give the name of the product formed when ethane undergoes monochlorination.

ANSWER: Chloroethane

SOLUTION:

Ethane has only one kind of hydrogen.