Title: 2010 Carbonyl Quiz 1

Feedback shared by this category's questions, if partly right: 1

Q: Which of the following oxidising agents is the most suitable for the oxidation of an alcohol to an aldehyde?
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A: [Image: Q8C] / [Image: Q8C] / [Image: Q8C] / [Image: Q8C] / [Image: Q8C] / [Image: Q8C]

Q: In the molecule pyridine the nitrogen atom (Z=7) is sp^2 hybridised. This means that the 2s and two of the 2p orbitals are hybridised to give an electron configuration where there are?
[Image: pyridine]
- Two sp^2 hybrid orbitals each containing one electron and one sp^2 hybrid orbital containing two electrons and one unhybridised sp orbital containing one electron
- Two sp^2 hybrid orbitals each containing two electron and one sp^2 hybrid orbital containing one electron
- Three sp^2 hybrid orbitals each containing one electron and one unhybridised sp orbital containing two electrons
- Two sp^2 hybrid orbitals each containing one electron and one unhybridised sp orbital containing one electron
A: Two sp^2 hybrid orbitals each containing one electron and one sp^2 hybrid orbital containing two electrons and one unhybridised sp orbital containing one electron

Q: Which of the following molecules has a dipole moment, CH_4, CH_3Cl, CH_2Cl_2, CH_3Cl, CCl_4?
- CH_3Cl, CH_2Cl_2, CH_3Cl, CCl_4
- CH_3Cl, CH_2Cl_2, CH_3Cl
- CH_3Cl, CH_3Cl, CCl_4
- CH_4, CH_3Cl, CH_2Cl_2, CH_3Cl, CCl_4
A: CH_3Cl, CH_2Cl_2, CH_3Cl

Q: The inductive effect is a long range effect that operates over many atoms.
- true
- false
A: false

Q: A nucleophile is a species that accepts a pair of electrons from an electrophile.
- true
- false
A: false

Q: Identify the atom indicated by the arrow in each molecule or ion as either an electrophilic or nucleophilic site.
- [Image: Q6EthBr] | Nucleophilic
- [Image: Q6Dimethamine] | Electrophilic
- [Image: Q6Cyanide] | Electrophilic
- [Image: Q6Carb] | Nucleophilic

Q: The most common reaction of aldehydes and ketones is the nucleophilic addition reaction. Here the nucleophile adds to the carbon of the carbonyl group to give an alkoxide anion. Which is the correct mechanism for this process?
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A: [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B] / [Image: Q7B]

Q: Which reducing agents are suitable for reducing aldehydes and ketones to alcohols?
- NaH
- NaBH_4
- LiClO_4
- LiAlH_4
A: NaBH_4; LiAlH_4

Q: Aldehydes are generally more reactive than ketones in nucleophilic addition reactions. Select the reasons from the following list that account for the higher reactivity of aldehydes.
- Aldehydes have only one non-hydrogen R group bonded to the carbonyl carbon atom resulting in less steric crowding.
- Ketones have two electron withdrawing R groups bonded to the carbonyl carbon atom decreasing their reactivity.
- Aldehydes are more polarised than ketones because they only have one R group bonded to the carbonyl carbon atom.
- Aldehydes have an electron releasing hydrogen atom bonded to the carbonyl carbon, which makes them electrophilic.
A: Aldehydes have only one non-hydrogen R group bonded to the carbonyl carbon atom resulting in less steric crowding.; Aldehydes are more polarised than ketones because they only have one R group bonded to the carbonyl carbon atom.

Q: Consider the following resonance structures and select the most reasonable statement from the list below.
[Image: Q14Question]
- The electron donating effect of the aromatic ring delocalises the positive charge and makes the carbonyl group less electrophilic and therefore less reactive in nucleophilic addition reactions.
- The electron withdrawing effect of the aromatic ring delocalises the positive charge and makes the carbonyl group more electrophilic and therefore more reactive in nucleophilic addition reactions.
- The high steric bulk of the aromatic ring decreases the reactivity of the aldehyde group to nucleophilic addition reactions.
A: The electron donating effect of the aromatic ring delocalises the positive charge and makes the carbonyl group less electrophilic and therefore less reactive in nucleophilic addition reactions.

Q: To increase the rate of reaction of carbonyl compounds with weak nucleophiles an acid catalyst is often added. What is the role of the acid catalyst?
- Protonation of the nucleophile increases its reactivity in nucleophilic addition reactions.
- Protonation of the carbonyl oxygen atom increases the electrophilic character of the carbonyl carbon atom.
- Addition of acid causes heating which increases the rate of reaction.
- Protonation of the carbonyl carbon atom increases the nucleophilic character of the carbonyl oxygen atom.
A: Protonation of the carbonyl oxygen atom increases the electrophilic character of the carbonyl carbon atom.

Q: What is the name of the class of compound formed in the following reaction?
[Image: Q11Grignard]
- Gilman reagent
- Lapworth reagent
- Grignard reagent
- Wolff-Kishner reagent
A: Grignard reagent

Q: What is the product of the following reaction?
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A: [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c] / [Image: Q13c]

Q: Treatment of an aldehyde or ketone with cyanide ion followed by protonation of the tetrahedral alkoxide intermediate, gives a cyanohydrin. What is the structure of the cyanohydrin fromed from cyclopentanone?
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A: [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D] / [Image: Q15D]

Q: A molecule is polar and has a dipole moment if "the centre of mass of all positive charges and the centre of mass of all negative charges are not coincidental".
- True
- False
A: True