Chapter 2 Multiple Choice Questions

Organic structure and bonding

Quiz Content

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. There are many properties of the element carbon which make it an important, almost unique, element. Which one of the following is perhaps the least important to a pharmacist (though nonetheless, is still interesting)?

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. The shape of a molecule is very important in pharmacy. Which of the following observations help to support this statement?
1. Shape governs the way in which a substrate binds to an enzyme
2. Shape governs the way in which a molecule may act as a drug
3. Shape (as well as the functional groups present) governs how a drug binds to a receptor site
4. Variations in three-dimensional shape can result in significant differences in the behaviour of a molecule in the human body

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. Which of the following electronic configurations is the best description of carbon in its ground state?

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. The compound shown below has the unsystematic name, oxotremorine. It has been investigated in the search for effective drugs to combat Parkinson's disease:
A 4 C alkyne chain. There are three parallel lines between C 2 and C 3. There is a single bond between C 1 and C 2 and C 3 and C 4. C 1 is single-bonded to a 5-membered heterocyclic pentagonal ring in a vertical orientation. It has 1 N and 4 C. N occupies the first position, which is the top right vertex. C 4 is single-bonded to a 5-membered heterocyclic pentagonal ring in a vertical orientation. It has 1 N and 4 C. N occupies the first position, which is bottom left. C 4 is double bonded to O.
Which of the following options gives the numbers of sp, sp2 and sp3 hybridised carbon atoms present (in that order) in this compound?

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. The structure of the sedative, ethchlorvinyl is shown below. What are the approximate bond angles around the three carbon atoms marked as 1, 2 and 3?
A 5-carbon alkyne chain. There are 3 parallel lines between C 1 and C 2, a single line between C 2 and C 4, and a zigzag line between C 4 and C 5. C 3 is single-bonded to O H below and single-bonded to a 2 C alkane chain. A double bond is between C 4 and C 5. C 5 is single-bonded to C l on the right. The bonds are numbered 1, 2, and 3.

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. The structure of the sedative ethchlorvinyl was shown in Question 5. Place the C≡C, C=C and C-C bonds in order of decreasing bond length (longest carbon to carbon bond first).

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. Which of the following is NOT an intermolecular force?

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. The two compounds shown below are the analgesics, paracetamol and phenacetin (phenacetin is the ethyl ether of paracetamol). Which one of the following statements concerning the hydrogen bonding of these compounds with water is not correct?
A molecular structure of paracetamol. A benzene ring is in a vertical orientation. A double bond is between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 1 is single-bonded to N above. N is single-bonded to H on the upper right. N is single-bonded to a central C atom on the upper left. The central C atom is double-bonded to O above and single-bonded to C H 3 on the lower left. A molecular structure of phenacetin. A benzene ring is in a vertical orientation. A double bond is between C 1 and C 2, C 3 and C 4, and C 5 and C 6. C 1 is single-bonded to N above. N is single-bonded to H on the upper right. N is single-bonded to a central C atom on the upper left. The central C atom is double-bonded to O above and single-bonded to C H 3 on the lower left. C 4 is single-bonded O C H 2 C H 3.

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. What process is being described by the following curly arrow?
A curved arrow pointing towards the right.

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. Which of the following examples illustrate the correct use of curly arrows in reaction mechanisms?
A chemical reaction. It has 2 reactants and 2 products. The first reactant is H O minus, and the second reactant is C H 3, single bond, C l. The arrow from the negative charge points toward the carbon of C H 3. The arrow from the single bond between C H 3 and C l points toward C l. The first product is H O C H 3 and the second product is C l minus.<br/>A chemical reaction. It has 2 reactants and one product. The first reactant is B r plus and the second reactant is H 2 C, double bond, C H 2. The product is H 2 C, single bond, C H 2. The curve from B r plus points to C H 2. Both C H 2 are single-bonded to a common B r. B r carries a positive charge.<br/>2 resonating structures. Left: H 3 C, single bond C. C is double-bonded to O on the upper right and single-bonded to O on the lower right. O carries a negative charge. An arrow from the negative charge on O points towards a single bond between O and C. A second arrow from the double bond between C and O points towards O. Right: H 3 C, single bond C. C is single-bonded to O on the upper right and double-bonded to O on the lower right. O on the upper right carries a negative charge. An arrow from the negative charge on O points towards a single bond between O and C. A second arrow from the double bond between C and O points towards O.<br/>A chemical reaction. It has 2 reactants and 1 product. The first reactant is H plus and the second reactant is H O minus. The arrow from the positive charge on H points towards H of H O. The product is H 2 O.

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