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Organic Chemistry Level 3

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Organic Chemistry Level 3

Answer every question. Show working or explain your reasoning where asked. Use structural formulae and correct organic chemistry terminology. Assume reactions occur under the conditions stated.

A. Functional groups and structure

A small flavour-and-fragrance company is comparing organic compounds before choosing ingredients for a product. Use the information in each question to identify structures and predict chemical behaviour.

1.The company tests CH₃CH₂CH₂OH. Which functional group does this compound contain?
  • Ester
  • Alcohol
  • Aldehyde
  • Ketone
2.Draw the structural formula of 2-methylpropanoic acid. Show all atoms and bonds in the carboxyl group.
3.Give the IUPAC name of CH₃–CH(CH₃)–CH₂–CH₃. Include the position number for the branch.
4.An unknown compound has formula C₃H₆O and contains a carbonyl group within its carbon chain. Is it an aldehyde or a ketone? Give one suitable structural formula and its name.

B. Reactions and reasoning

The company now considers how to make and identify a set of useful organic compounds.

5.Hydrogen is added to 1-butene in the presence of a palladium catalyst. Name the product and state the type of reaction.
6.Which reagent and conditions will oxidise a primary alcohol all the way to a carboxylic acid?
  • NaBH₄ in ethanol
  • Warm, acidified KMnO₄ with the mixture heated under reflux
  • H₂ with a palladium catalyst
  • PCC with the aldehyde distilled off
7.Ethanol reacts with ethanoic acid to form ethyl ethanoate and water. Write the balanced equation using condensed structural formulae, and name the reaction type.
8.Match each reagent to the transformation it commonly performs.
  • A. SOCl₂
  • B. H₂ / Pd
  • C. NaBH₄
  • D. Warm, acidified KMnO₄
  • 4. Adds hydrogen across an alkene C=C bond
  • 1. Reduces a ketone to a secondary alcohol
  • 2. Converts a carboxylic acid to an acyl chloride
  • 3. Oxidises a primary alcohol to a carboxylic acid under vigorous conditions
9.Nucleophilic acyl substitution converts an acyl chloride into a different acyl compound. Describe the two key stages of the mechanism, referring to the roles of the nucleophile and the leaving group.

C. Use the evidence

A student records these infrared absorption ranges while checking two samples. Wavenumbers are given in cm⁻¹.

Sample

Strong absorption near

Broad absorption

P

1,710 cm⁻¹

2,500–3,300 cm⁻¹

Q

1,740 cm⁻¹

None in this range

10.Use the infrared evidence grid. Which sample is more likely to be a carboxylic acid, and which is more likely to be an ester? Explain how the absorptions support your choices.

3 printable pages

  • Organic Chemistry Level 3, page 1 of 3: A. Functional groups and structure

    Page 1

  • Organic Chemistry Level 3, page 2 of 3: B. Reactions and reasoning

    Page 2

  • Organic Chemistry Level 3, page 3 of 3: C. Use the evidence

    Page 3

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