Question

1. Draw the Fisher projection of (2R, 4S) methyl 4-amino-4-chloro-2-methoxypentanoate. Be careful to indicate proper stereochemistry designation for all chiral centers. 2. Provide a perspective drawing of (2S)-2-amino-2-(bromomethyl) pentane-1-thiol. 3. Provide the proper IUPAC name for the alkene shown below. 4. Draw the least and most stable chair conformation of cis-1-methoxy-3-(propan-2-yl) cyclohexane. Show the ring flip. 5. The specific rotation of (S)-(+)-glyceraldehyde is (+) 6.4°. If a given mixture has an observed rotation of (-)4.8°, then what is the composition of a mixture of glyceraldehyde enantiomers? 6. Draw the Newman projections of the least and the most stable conformers of 3,4-dichloropentane-2-thiol, when viewed along the C2-C3 bond. 7. Which of the following compounds will undergo an SN2 reaction most readily? A) (CH3)3CCH2I B) (CH3)3CCl C) (CH3)2CHI D) (CH3)2CHCH2CH2CH2I E) (CH3)2CHCH2CH2CH2Cl 8. Assign the E or Z configuration to the following molecule. 9. Indicate the step-wise mechanism and the final product(s) of the following reaction. 10. Rank the species below in order of increasing nucleophilicity in polar aprotic solvents: CH3CO2-, CH3S-, HO-, F-, CH3CH2NH-. 11. The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways? A) SN1 B) SN2 C) E1 D) E2 E) No reaction

          1. Draw the Fisher projection of (2R, 4S) methyl 4-amino-4-chloro-2-methoxypentanoate. Be careful to indicate proper stereochemistry designation for all chiral centers.
2. Provide a perspective drawing of (2S)-2-amino-2-(bromomethyl) pentane-1-thiol.
3. Provide the proper IUPAC name for the alkene shown below.
4. Draw the least and most stable chair conformation of cis-1-methoxy-3-(propan-2-yl) cyclohexane. Show the ring flip.
5. The specific rotation of (S)-(+)-glyceraldehyde is (+) 6.4°. If a given mixture has an observed rotation of (-)4.8°, then what is the composition of a mixture of glyceraldehyde enantiomers?
6. Draw the Newman projections of the least and the most stable conformers of 3,4-dichloropentane-2-thiol, when viewed along the C2-C3 bond.
7. Which of the following compounds will undergo an SN2 reaction most readily?
A) (CH3)3CCH2I
B) (CH3)3CCl
C) (CH3)2CHI
D) (CH3)2CHCH2CH2CH2I
E) (CH3)2CHCH2CH2CH2Cl
8. Assign the E or Z configuration to the following molecule.
9. Indicate the step-wise mechanism and the final product(s) of the following reaction.
10. Rank the species below in order of increasing nucleophilicity in polar aprotic solvents: CH3CO2-, CH3S-, HO-, F-, CH3CH2NH-.
11. The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?
A) SN1
B) SN2
C) E1
D) E2
E) No reaction

1. Draw the Fisher projection of (2R, 4S) methyl 4-amino-4-chloro-2-methoxypentanoate. Be careful to indicate proper stereochemistry designation for all chiral centers.
2. Provide a perspective drawing of (2S)-2-amino-2-(bromomethyl) pentane-1-thiol.
3. Provide the proper IUPAC name for the alkene shown below.
4. Draw the least and most stable chair conformation of cis-1-methoxy-3-(propan-2-yl) cyclohexane. Show the ring flip.
5. The specific rotation of (S)-(+)-glyceraldehyde is (+) 6.4°. If a given mixture has an observed rotation of (-)4.8°, then what is the composition of a mixture of glyceraldehyde enantiomers?
6. Draw the Newman projections of the least and the most stable conformers of 3,4-dichloropentane-2-thiol, when viewed along the C2-C3 bond.
7. Which of the following compounds will undergo an SN2 reaction most readily?
A) (CH3)3CCH2I
B) (CH3)3CCl
C) (CH3)2CHI
D) (CH3)2CHCH2CH2CH2I
E) (CH3)2CHCH2CH2CH2Cl
8. Assign the E or Z configuration to the following molecule.
9. Indicate the step-wise mechanism and the final product(s) of the following reaction.
10. Rank the species below in order of increasing nucleophilicity in polar aprotic solvents: CH3CO2-, CH3S-, HO-, F-, CH3CH2NH-.
11. The major product from the reaction of 2-chloro-2-methylpentane with sodium ethoxide in ethanol results from which of the following mechanistic pathways?
A) SN1
B) SN2
C) E1
D) E2
E) No reaction

Added by Kimberly P.

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