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QUESTIONS

These are the questions that appear in the course notes and are by no means exhaustive! Use pen and paper to work out the answers and then check them against those on the answer page accessed by clicking "answers" at the end of each section. If you are not sure of the answer go back to the appropriate page of the course notes.

INTRODUCTION

Name the functional groups in the following molecules:

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ALKANES

Draw all the constitutional isomers of C₅H₁₂ and C₆H₁₄.

Draw the Newman projections of the conformers representing the maximum and minimum points on the energy profile. Draw the energy profile of a butane molecule as the C2-C3 bond is rotated through 360° .

Name the following compounds:

Classify the following pairs of molecules as Constitutional isomers, Conformational isomers or Diastereoisomers.

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ALKENES

Give the names of the following molecules:

Name these molecules (include Z and E where appropriate)

Name these molecules:

Draw the curly arrow in the following reaction:

Use arrow notation to illustrate the mechanism of the reaction of Br₂ with propene. Label each species electrophile or nucleophile.

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ALKYNES

Name the following compounds

Predict the products in the following reactions:

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AROMATIC COMPOUNDS

Fill in the missing reagents or products in the following reactions:

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SPECTROSCOPY

What is the value of m/z of the molecular ions (integer values) of the following compounds?

Which of the following compounds strongly absorb electronic radiation in the ultraviolet-visible region of the spectrum ?

Which of the compounds: CH₃CH₂COCH₃, CH₃CH₂OCH₃, CH₃CH₂CH₂OH, is the following infrared spectrum representative of?

Indicate which of the following compounds absorb around 1700 cm^-1 and around 3500 cm^-1 in the infrared region.

A compound with molecular formula C₃H₈O has a strong absorption at 3600 cm^-1 in the infrared spectrum. Give a reasonable condensed structural formula for any compound whose structure is consistent with this data.

How many signals would be expected in the ¹H NMR spectrum of each of the following compounds?

Give the ratio of signal sizes observed in the ¹H NMR spectrum of each of the following molecules:

Give the number of signals, their relative intensities and the multiplicities in the ¹H NMR spectra of each of the following compounds:

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ALCOHOLS

Name and classify the following alcohols as primary, secondary or tertiary

What reagents are used in the following reactions?

Draw curly arrows to describe the nucleophilic substitution reaction of 2-propanol with concentrated HI to form 2-iodopropane

Draw the product formed in the following reactions:

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ORGANIC HALOGEN COMPOUNDS

Predict the products from the following reactions:

Name and classify (1° , 2° , 3° or aryl) the following halogen compounds:

Fill in the reagents in the following reaction scheme:

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ALDEHYDES AND KETONES

Name the following compounds

Fill in the reagents in the following transformations:

Use curly arrow notation to indicate the mechanism of nucleophilic addition of methyl magnesium bromide to acetone followed by treatment with aqueous acid.