Organic Chem summer test 2

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Ch 5, 6, and 7 Pearson

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171 Terms

1
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________ are isomers which have the same bonding sequence but differ in the orientation of their atoms in space.

Stereoisomers

2
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What is the structural relationship between the two molecule shown below?

The figure shows the structures of two molecules with the same carbon skeleton. A six-carbon ring, with a one-membered carbon bridge between the first and the fourth (clockwise) carbon atoms. In the first structure, there is a Cl atom bonded to the sixth carbon above the ring. In the second structure, a Cl atom is bonded to the first carbon.

constitutional isomers

3
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How many enantiomers are there of the molecule shown below?

There is a Fischer projection for a molecule. The carbon chain is depicted vertically, with a CO2H group at the top and a CH2OH group at the bottom, while the three remaining carbon atoms are represented by the center of crossing lines. The molecule has all hydroxyls on the right and hydrogens opposite to them.

1

4
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two molecular structures. The first structure is as follows: the central C atom, with a CH3 group at the top position, an H atom at the left position, an NH2 group at the right position bonded to the central C with a wedge, and a CO2H group at the right position bonded to the central C with a dash. The second structure is a Fischer projection for a molecule. The carbon chain is depicted vertically with a CO2H group at the top and a CH3 group at the bottom, while the remaining carbon atom is represented by the center of crossing lines. The molecule has an NH2 group on the left and an H atom opposite to it.

the same compound

5
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two molecular structures. The first structure is as follows: the central C atom, with a Cl atom at the top position, an H atom at the left position, an F atom at the right position bonded to the central C atom with a wedge, and a Br atom at the right position bonded to the central C atom with a dash. The second structure is as follows: the central C atom, with an F atom at the top position, a Cl atom at the right position, a Br atom at the left position bonded to the central C atom with a wedge, and an H atom bonded to the central C atom with a dash.

the same compound

6
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two molecular structures. The first structure is as follows: the central C atom, with a Br atom at the top position, a CH3 group at the left position, a CH2CH3 group at the right position bonded to the central C atom with a wedge, and an H atom at the right position bonded to the central C atom with a dash. The second structure is a Fischer projection for a molecule. The carbon chain is depicted vertically with a CH3 group at the top and a CH2CH3 group at the bottom, while the remaining carbon atom is represented by the center of crossing lines. The molecule has a Br atom on the right and an H atom on the left.

enantiomers

7
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Is the molecule shown below chiral or achiral?

(CH3)3CCH(CH3)2

achiral

8
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How many asymmetric carbon atoms are present in the following compound?

A six-carbon ring, with a CH left parenthesis CH3 right parenthesis 2 group attached to the first carbon with a wedge and two CH3 groups attached to the third (clockwise) carbon with a wedge and with a dash.

1

9
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How many asymmetric carbon atoms are present in the following compound?

A five-membered ring, with an O atom double-bonded to the second (clockwise) and to the fifth members of the ring, a CH3 group attached to the third and the fourth members, and a double bond between the third and the fourth members of the ring. The first member of the ring is an O atom, while the other are C atoms.

0

10
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How many asymmetric carbons are present in the compound below?

A six-carbon ring, with a double bond between the first and the second (clockwise) carbon atoms and between the third and the fourth carbon atoms. A CH3 group is attached to the second carbon atom, and a CH left parenthesis CH3 right parenthesis 2 group and an H atom are bonded to the fifth carbon with a wedge and with a dash, correspondingly.

1

11
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How many asymmetric carbons are present in the compound below?

The figure shows a molecule with the following structure: two fused six-carbon rings, where the second and the third (clockwise) carbons of the left ring are common with the fifth and the sixth carbons of the right ring. The left ring has alternating double and single bonds. The right ring has an OCNHCH3 group, with an O atom double-bonded to the first (from left to right) carbon bonded to the second carbon and a double bond between the first and the second and the third and the fourth carbons.

0

12
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How many asymmetric carbons are present in the compound below?

The figure shows a six-membered ring in the chair conformation. In this conformation, a six-membered ring is shown as a non-planar structure, where the second, the third, the fifth, and the sixth atoms are located in the same plane, the first atom is located above the plane, and the fourth atom is located below the plane. The OH group at the first and the fifth atoms is slanted down, and the OH group at the fourth and the sixth atoms is slanted up. A CH2OH group at the second atom is slanted up. The third atom of the ring is oxygen, while the other atoms are carbons.

5

13
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How many asymmetric carbon atoms are present in the molecule shown?

A five-carbon chain, with a Cl atom bonded to the first (from right to left) and the second carbon atoms.

1

14
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How many asymmetric carbon atoms are present in the molecule shown?

A five-carbon chain, with a Cl atom bonded to the second (from right to left) and the third carbon atoms.

2

15
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Is the mirror image of the following molecule an enantiomer or is it superimposable with it?

The figure shows a molecule with the following structure: a six-carbon ring, with a one-membered carbon bridge between the first and the fourth (clockwise) carbon atoms and a double bond between the fifth and the sixth carbon atoms. A CH3 group and a hydrogen atom are bonded to the bridge carbon in such a way that the CH3 group is above the double bond.

superimposable

16
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two structures. The first structure is as follows: a five-carbon ring, with a CH3 group attached to the first carbon with a dash and a Cl atom bonded to the second (clockwise) and the third carbons with a wedge. The second structure is as follows: a five-carbon ring, with a CH3 group attached to the first carbon with a dash and a Cl atom bonded to the second (counter-clockwise) and the third carbons with a wedge.

enantiomers

17
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Which of the statements below correctly describes an achiral molecule?

The molecule has a nonsuperimposable mirror image.

The molecule might be a meso form.

The molecule exhibits optical activity when it interacts with plane-polarized light.

The molecule has an enantiomer.

None of the above

The molecule might be a meso form.

18
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Choose each chiral molecule among those shown below.

A six-carbon ring, with an OH group bonded to the first carbon with a wedge and a Cl atom bonded to the fourth (clockwise) atom with a dash.A five-carbon ring, with a Br atom bonded to the first carbon with a wedge and a double bond between the fourth (clockwise) and the fifth carbon atoms.A five-carbon chain, with a Br atom bonded to the second (from left to right) and the fourth carbon atoms with a wedge.

A five-carbon ring, with a Br atom bonded to the first carbon with a wedge and a double bond between the fourth (clockwise) and the fifth carbon atoms.

19
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Is the molecule shown below chiral or achiral?

CH3CH2CH(CH3)CH2CH3

achiral

20
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Is the molecule shown below chiral or achiral?

There is a four-carbon ring, with an OH group bonded to the first carbon with a wedge.

achiral

21
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Is the molecule shown below chiral or achiral?

The figure shows a molecule with the following structure: a central C atom, with a CH2OH group at the top position, a CO2H group at the right position, an H atom at the left position bonded to the central C atom with a wedge, and a CO2H group at the right position bonded to the central C atom with a dash.

achiral

22
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Is the molecule shown below chiral or achiral?

The figure shows a molecule with the following structure: a six-carbon ring, with a one-membered carbon bridge between the first and the fourth (clockwise) carbon atoms. Two CH3 groups are attached to the second carbon atom, and an O atom is double-bonded to the third carbon atom.

chiral

23
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How many asymmetric carbons are present in the compound below?

3-ethyl-2,2,4-trimethylpentane

1

24
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two molecules. The first molecule (from left to right) has the following structure: a six-carbon ring, with a CH3 group attached to the first carbon with a wedge and an OH group bonded to the second (clockwise) carbon with a dash. The second molecule has the following structure: a six-carbon ring, with an OH group bonded to the first carbon with a dash and a CH3 group attached to the second (clockwise) carbon with a wedge.

enantiomers

25
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Is the molecule shown below chiral or achiral?

A six-carbon ring, with a CH3 group attached to the first carbon with a wedge and an OH group attached to the fourth (clockwise) carbon with a dash.

achiral

26
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Does the molecule shown below contain asymmetric carbon atoms?

A six-carbon ring, with a Cl atom bonded to the first carbon with a wedge and to the fourth (clockwise) carbon with a dash and a Br atom bonded to the second carbon with a wedge and to the fifth carbon with a dash.

yes

27
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Is this molecule chiral?

A six-carbon ring, with a Cl atom bonded to the first carbon with a wedge and to the fourth (clockwise) carbon with a dash and a Br atom bonded to the second carbon with a wedge and to the fifth carbon with a dash.

No

28
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term image

Top R

Bottom S

29
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Which of the following configurations corresponds to the structure below?

There is a five-membered ring, with a double bond between the second and the third (clockwise) atoms, a CH left parenthesis CH3 right parenthesis 2 group attached to the fourth atom with a wedge, and an OCH3 group bonded to the fifth atom with a dash. The first atom is oxygen, while the rest are carbons. All atoms of the ring are labeled with numbers.

4-R

5-R

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term image

top S

Bottom S

31
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Compounds that rotate the plane of polarized light clockwise are called ________.


dextrorotatory

32
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Which of the following statements is (are) true for the compound (RR)-2-butanol?

This compound is optically active.

This compound is chiral.

This compound has an enantiomer.

33
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Which of the following statements correctly pertains to a pair of enantiomers?

They rotate the plane of polarized light by exactly the same amount and in opposite directions.

34
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If (SS)-glyceraldehyde has a specific rotation of -8.7°, what is the specific rotation of (RR)-glyceraldehyde?

+8.7°

35
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Predict the specific rotation of the compound shown.

A six-carbon ring, with a CH3 group attached to the first and the fourth (clockwise) carbons with a wedge.

Zero; the compound is achiral.

36
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Given that glucose has a specific rotation of +52.8°. Predict the concentration of a glucose aqueous solution contained in a 10 cm long polarimetry tube if a rotation of +15.8° was observed.


0.299 g/mL

37
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A student measured the optical activity of an unknown sugar at two different concentrations. The results of his measurements are shown below. Given that the sample cell had a path length of 10.0 cm, calculate the specific rotation for the unknown sugar. (Hint: Consider each measurement of plane polarized light has a true reading and a "ghost" reading 180° from the true reading).

concentration

observed rotation

2.00 g sugar in 10.0 mL water

+159.1∘

5.00 g sugar in 10.0 mL water

+127.8∘

-105∘


38
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A newly isolated natural product was shown to be optically active. If a solution of 2.0 g in 10 mL of ethanol in a 50 cm tube gives a rotation of +2.57°, what is the specific rotation of this natural product?


+2.57°

39
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A mixture of equal amounts of two enantiomers ________.


statements "is called a racemic mixture" and "is optically inactive" are correct

40
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If a mixture contains 75% of one compound and 25% of its enantiomer, what is the e.e. of the mixture?


50

41
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Calculate the e.e. of a mixture containing 8.0 g of (-)-glyceraldehyde and 2.0 g of (+)-glyceraldehyde.


60

42
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A mixture of two enantiomers with a composition of 65.0% R has an observed rotation of -25.3° in a 10.0 cm polarimeter tube. If the mixture has a concentration of 2.038 g/mL at 25°C, what is the predicted [α]25D of an optically pure sample of the S enantiomer?


+41.3°

43
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(-)-Lactic acid has a specific rotation of -3.8°. What is the specific rotation of a solution containing 7.5 g of (-)-lactic acid and 2.5 g of (+)-lactic acid?


-1.9°

44
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Can the molecule shown below be properly described as a meso compound?

A six-carbon ring, with a two-membered carbon bridge between the first and the fourth (clockwise) carbons.

no

45
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Is the molecule shown below chiral or achiral?

The figure shows a molecule with the following structure: CCC with a double bond between the first and the second (from left to right) C atoms and the second and the third C atoms. Two H atoms are bonded to the first carbon. A CH3 group is attached to the third carbon with a dash, and a CO2H group is attached to the third carbon with a wedge. The H atoms of the first carbon and the CH3 and the CO2H groups of the third carbon are depicted in perpendicular planes.

achiral

46
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows structures of two compounds. Both compounds have the following carbon skeleton: two six-carbon rings with alternating double and single bonds linked with a single bond between the first carbons of the rings. The right ring lies in the plane that is perpendicular to the plane of the left ring. An H atom is bonded to the second (clockwise) carbon of the left ring, and a CH3 group is bonded to the sixth carbon of the left ring. In the first structure, a CH3 group is attached with a dash to the second (clockwise) atom of the right ring, and an NO2 group is bonded with a wedge to the sixth carbon of the right ring. In the second structure, an NO2 group is bonded with a dash to the second (clockwise) carbon of the right ring, and a CH3 group is bonded with a wedge to the sixth carbon of the right ring.

enantiomers

47
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How many asymmetric carbons are present in the compound below?

The figure shows a Fischer projection for a molecule. The carbon chain is depicted vertically, with a CO2H group at the top and at the bottom, while the two remaining carbon atoms are represented by the center of crossing lines. The molecule has all hydroxyls on the right and hydrogens opposite to them.

2

48
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How many diastereomers are there of the molecule shown below?

A five-carbon ring, with an OH group bonded to the first carbon with a wedge and to the third (clockwise) carbon with a wedge.

2

49
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Stereoisomers which are not mirror image isomers are ________.

diastereomers

50
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Which of the following terms best describes the stereochemical relationship of the two compounds shown below in Fischer notation?

The figure shows two Fischer projections. In both projections, a carbon chain is depicted vertically. In the first structure, a CH3 group is at the top, and a C2H5 group is at the bottom, while the two remaining carbons are represented by the center of crossing lines. A Br atom is bonded to the first carbon (from top to bottom) on the left with a hydrogen atom opposite to it, while a Cl atom is bonded to the second carbon on the right with a hydrogen atom opposite to it. In the second structure, a C2H5 group is at the top, and a CH3 group is at the bottom, while the two remaining carbons are represented by the center of crossing lines. A Cl atom is bonded to the first (from top to bottom) carbon on the left with a hydrogen opposite to it, while a Br atom is bonded to the second carbon on the left with a hydrogen atom opposite to it.

diastereomers

51
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Which of the following terms correctly describe(s) the structural relationship between cis-1,3-dimethylcyclopentane and trans-1,3-dimethylcyclopentane?


both diastereomers and geometric isomers

52
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two structures with a six-carbon ring. In the first structure, a CH3 group is bonded to the first carbon with a wedge, and a Cl atom is bonded to the second (clockwise) carbon with a wedge. In the second structure, a CH3 group is bonded to the first carbon with a wedge, and a Cl is bonded to the sixth carbon (clockwise) with a dash.

diastereomers

53
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two structures with a five-carbon chain. In the first structure, an OH group is bonded above to the second carbon with a wedge, and a CH3 group is bonded below to the third carbon with a dash. In the second structure, an OH group is bonded above to the fourth (from left to right) carbon with a dash, and a CH3 group is bonded below to the third carbon with a wedge.

the same compound

54
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Which of the following statements is (are) true for the compound (3RR, 4RR)-3,4-dimethylhexane?

This compound is a diastereomer of (3RR, 4SS)-3,4-dimethylhexane.

The enantiomer of this compound is (3SS, 4SS)-3,4-dimethylhexane.

This compound is chiral.

55
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How many diastereomers are there of the molecule shown below?

The figure shows a Fischer projection for a molecule. The carbon chain is depicted vertically, with a CO2H group at the top and a CH2OH group at the bottom, while the three remaining carbon atoms are represented by the center of crossing lines. The presented molecule has all hydroxyls on the right and hydrogens opposite to them.

6

56
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The figure shows the first structure. There is a Newman projection. CH2OH, OH, and H are attached to the front carbon (clockwise). CH2OH, OH, and H are attached to the back carbon (clockwise). Furthermore, the CH2OH group of the front carbon is located between the OH group and the H atom of the back carbon.The figure shows the second structure. There is a Fischer projection for a molecule. The carbon chain is depicted vertically, with a CH2OH group at the top and at the bottom, while the two remaining carbon atoms are represented by the center of crossing lines. The presented molecule has one hydroxyl group attached to the first (from top to bottom) carbon on the right and the other hydroxyl group attached to the second carbon on the left and hydrogen atoms opposite to them.The figure shows the third structure. A four-carbon chain, with an OH group attached above to the second (from left to right) carbon with a wedge, attached below to the third carbon with a wedge, and single-bonded to the first and the fourth carbons.

The relationship between I and III is: ________.

diastereomers

57
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The figure shows the first structure. There is a Newman projection. CH2OH, OH, and H are attached to the front carbon (clockwise). CH2OH, OH, and H are attached to the back carbon (clockwise). Furthermore, the CH2OH group of the front carbon is located between the OH group and the H atom of the back carbon.The figure shows the second structure. There is a Fischer projection for a molecule. The carbon chain is depicted vertically, with a CH2OH group at the top and at the bottom, while the two remaining carbon atoms are represented by the center of crossing lines. The presented molecule has one hydroxyl group attached to the first (from top to bottom) carbon on the right and the other hydroxyl group attached to the second carbon on the left and hydrogen atoms opposite to them.The figure shows the third structure. A four-carbon chain, with an OH group attached above to the second (from left to right) carbon with a wedge, attached below to the third carbon with a wedge, and single-bonded to the first and the fourth carbons.

The relationship between I and II is: ________.

diastereomers

58
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two structures. The first one is a Newman projection for a molecule. OH, CH3, and H are attached to the front carbon atom (clockwise). OH, H, and CH3 are attached to the back carbon atom (clockwise). Furthermore, the OH group of the front carbon is located between the CH3 group and the H atom of the back carbon atom. The second structure is a Fischer projection for a molecule. The carbon chain is depicted vertically, with a CH3 group at the top and at the bottom, while the two remaining carbon atoms are represented by the center of crossing lines. The presented molecule has all hydroxyls on the right and hydrogens opposite to them.

diastereomers

59
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Which of the following terms best describes the pair of compounds shown: enantiomers, diastereomers, or the same compound?

The figure shows two structures. The first structure is a Newman projection for a molecule. Cl, CH3, and H are attached to the front carbon atom (clockwise). Cl, CH3, and H are attached to the back carbon (clockwise). Furthermore, the Cl atom of the front carbon is located between the CH3 group and H atom of the back carbon. The second structure is a four-carbon chain, with a Cl atom bonded above to the second (from left to right) carbon with a wedge and bonded below to the third carbon with a dash.

the same compound

60
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Can the molecule shown below be properly described as a meso compound?

A five-carbon ring, with a CH3 group attached to the first and the third (clockwise) carbons with a dash.

yes

61
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How many enantiomers are there of the molecule shown below?

A five-carbon ring, with an OH group bonded to the first and the third (clockwise) carbons with a wedge.

0

62
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Which of the following statements is (are) true for the compound cis-1,2-dichlorocyclopropane?


None of the above

63
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Draw the structure of the meso form of 1,3-dichlorocyclopentane. Take particular care to indicate three-dimensional stereochemical detail properly.

knowt flashcard image
64
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Can the molecule shown below be properly described as a meso compound?

(CH3)2CHCH2CH3


No

65
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Which of the following is classified as a vinylic halide?

CH3CH=CHCl

66
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The flame retardant below has been found to be an androgen agonist and may have a contribution to an increasing rate of occurrence of prostate cancer (J. Med. Chem. 2006, 7366). What is the correct term that describes the relative position of the bromides in this structure?

A six-carbon ring, with a CHCH2 group, which has a Br atom bonded to its first and second carbons, attached to the first carbon and a Br atom bonded to the third (clockwise) and the fourth carbon atoms of the ring.

vicinal

67
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What general classification is given to the molecule below?

A six-carbon ring, with a one-membered carbon bridge between the first and the fourth (clockwise) carbon atoms and a double bond between the fifth and the sixth carbon atoms. A Cl atom is bonded to the first carbon of the ring.

tertiary chloride

68
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Provide the name of the bromoalkane shown below.

A six-carbon chain, with a CHCH2CH3 group, with a Br atom bonded to the first (from left to right) carbon attached to the third (from left to right) carbon.

3-bromo-4-ethylheptane

69
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Provide an acceptable name for CHCl3.

trichloromethane

70
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Provide an acceptable name for CH3CH2CH2C(CH3)2I.

2-iodo-2-methylpentane

71
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Provide an acceptable name for the compound shown below.

A five-carbon ring, with a Cl atom bonded to the first and the second (clockwise) carbons with a wedge.

cis-1,2-dichlorocyclopentane

72
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Provide the structure of isopropyl iodide.

knowt flashcard image
73
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Which of the following is a secondary halide?

(CH3)3CCHClCH3

74
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Which of the following is a tertiary halide?

(CH3)2CClCH2CH3

75
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Which of the following is a geminal dihalide?

3,3-dichloropentane

76
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Which of the following is a vicinal dihalide?

cis-1,2-dibromocyclopentane

77
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Which of the following is a secondary alkyl halide?

isopropyl chloride

78
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Which of the following is a primary alkyl halide?

isobutyl chloride

79
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The following structure is a proteasome inhibitor that may find application in treating cervical cancer (J. Med. Chem. 2011, 449). The halides in this structure may be classified as ________ and ________.

The figure shows a proteasome inhibitor, which has the following structure: a six-membered ring with an O atom double-bonded to the first atom. A carbon atom is double-bonded to the second (clockwise) and the sixth carbons. A six-carbon ring, with alternating double and single bonds and a Cl atom bonded to the fourth and the fifth (clockwise) carbons, is bonded to the attached carbon. The fourth atom of the central ring is nitrogen, while the rest are carbons.

vicinal & aryl

80
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Which of the following alkyl halides has the smallest molecular dipole moment?

CF4

81
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Among the following alkyl halides, choose the one with the lowest boiling point.

tt-butyl chloride

82
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When water is shaken with dichloromethane, a two-phase system results. Which compound forms the upper phase?

water

83
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Provide the structure of the major organic product in the reaction below.

There is a partial scheme of a reaction, where a five-carbon ring, with a double bond between the first and the second (clockwise) carbons, reacts with NBS.

knowt flashcard image
84
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Consider the reaction of (CH3)3CO- with iodomethane. Will the reaction rate increase, decrease, or remain the same if the concentration of iodomethane is increased?

will increase

85
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What type of intermediate is present in the SN2 reaction of cyanide with bromoethane?


This reaction has no intermediate.

86
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Which of the following species is the least nucleophilic?

BF3

87
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Which of the following compounds is the most nucleophilic?

CH3SH

88
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Arrange the following species in order of decreasing nucleophilicity:

CH3CH2S- > CH3CH2O- > (CH3)3CO- >(CH3)3COH

89
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Rank the species below in order of decreasing nucleophilicity in hydroxylic solvents:

CH3S- > HO- > CH3CO2 - >H2O.

90
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Which of the following factors is favorable for nucleophilicity but not basicity?

highly polarizable

91
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Which of the following solvents could be described as polar and protic?

ethanol

92
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Which of the following compounds will undergo an SN2 reaction most readily?

(CH3)2CHCH2CH2CH2I

93
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Which of the following alkyl chlorides will undergo SN2 reaction most readily?

1-chloro-4-methylpentane

94
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Arrange the following substrates in order of their decreasing SN2 reactivity with NaCN:

Bromoethane > 1-chloro-3,3-dimethylpentane > 1-chloro-2,2-dimethylpentane > 2-bromo-2-methylpentane

95
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List the following bromides in order of their decreasing reactivity as substrates in SN2 reactions:

PhCH₂Br > PhCH(CH₃)Br > PhBr

96
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List the following alkyl halides in order of their decreasing reactivity as substrates in SN2 reactions:

1-iodobutane > 2-iodobutane > 2-chlorobutane

97
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Which of the following statements describe a favorable attribute of a leaving group?

The leaving group should be highly polarizable.

The departed leaving group should have low basicity

98
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Which of the following alkyl halides reacts most rapidly via an SN2 reaction with NaCN?

1-iodohexane

99
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SN2 reactions take place with ________ of stereochemistry at the center undergoing substitution.

inversion

100
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Provide the major organic product of the reaction below.

There is a partial scheme of a reaction, where a five-carbon chain, with an I atom bonded above to the fourth (from left to right) carbon with a wedge, reacts with NaSCH3.

knowt flashcard image