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Assign priorities to the groups in each set. (a) \(-\mathrm{H}-\mathrm{CH}_{1}-\mathrm{OH}-\mathrm{CH}_{2} \mathrm{OH}\) (b) \(-\mathrm{CH}_{2} \mathrm{CH}=\mathrm{CH}_{2}-\mathrm{CH}=\mathrm{CH}_{2}-\mathrm{CH}_{3}-\mathrm{CH}_{2} \mathrm{COOH}\) (c) \(-\mathrm{CH}_{3}-\mathrm{H}=\mathrm{COO}^{-}-\mathrm{NH}_{3}{ }^{+}\) (d) \(-\mathrm{CH}_{3}-\mathrm{CH}_{2} \mathrm{SH}-\mathrm{NH}_{3}+-\mathrm{CHO}\)

Short Answer

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Question: Arrange the functional groups in each molecule according to their priority based on atomic numbers. (a) -OH, -CH2OH, -CH, -H (b) -CH2COOH, -CH2CH=CH2, -CH=CH2 (c) =COO-, -NH3+, -CH3, -H (d) -NH3+, -CHO, -CH2SH, -CH3

Step by step solution

01

Determine functional groups

In each molecule, we need to first identify the functional groups present, which will help us assign priorities later on. (a) In this molecule, we have the following functional groups: -H, -CH, -OH, and -CH2OH (b) The functional groups present in this molecule are: -CH2CH=CH2, -CH=CH2, and -CH2COOH (c) The functional groups in this molecule are: -CH3, -H, =COO-, and -NH3+ (d) The functional groups in this molecule are: -CH3, -CH2SH, -NH3+, and -CHO
02

Assign priorities based on atomic number

Now that we have identified the functional groups in each molecule, we will assign priorities based on the atomic numbers of the atoms in each functional group. (a) In this molecule, the functional groups are: 1. -OH (O: atomic number 8) 2. -CH2OH (also contains oxygen with atomic number 8) 3. -CH (C: atomic number 6) 4. -H (H: atomic number 1) (b) In this molecule, the functional groups are: 1. -CH2COOH (contains oxygen with atomic number of 8) 2. -CH2CH=CH2 (contains carbon with atomic number of 6, and three carbon atoms in the group) 3. -CH=CH2 (contains carbon with atomic number of 6, and two carbon atoms in the group) (c) In this molecule, the functional groups are: 1. =COO- (contains oxygen with atomic number of 8) 2. -NH3+ (contains nitrogen with atomic number of 7) 3. -CH3 (contains carbon with atomic number of 6) 4. -H (contains hydrogen with atomic number of 1) (d) In this molecule, the functional groups are: 1. -NH3+ (contains nitrogen with atomic number of 7) 2. -CHO (contains oxygen with atomic number of 8) 3. -CH2SH (contains sulfur with atomic number of 16) 4. -CH3 (contains carbon with atomic number of 6)

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Most popular questions from this chapter

If priority cannot be assigned on the basis of the atoms bonded directly to the chiral center [because of a tie (i.e., the same first atom on more than one substituent)], look at the next set of atoms and continte tuntil a priority can be assigned. Priority is assigned at the first point of difference. Following is a series of groups arranged in order of increasing priority. The atomic number of the atom on which the assignment of priority is based is shown above it.

Think about the helical coil of a telephone cord or a spiral binding. Suppose that you view the spiral from one end and find that it is a left-handed twist. If you view the same spiral from the other end, is it a right-handed or left- handed twist?

Draw mirror images for these molecules. Are they different from the original molecule? (a) CC(O)C(=O)O (b) O=CC(O)CO (c) CC(N)C(=O)O (d) OC1CCCO1 (e) OC1CCCCC1 (f) CC1CCCCC1O (g) CC1CCCCC1O (h) CC1CC(C)C(O)C1O

Mark each chiral center in the following molecules with an asterisk. How many stereoisomers are possible for each molecule? (a) CC(O)C(O)C(=O)O (b) [O]C(C(=O)O)C(CC(=O)O)C(=O)O (c) CC1=CCC(C(C)C)CC1 (c) CC1CCC(C(C)C)CC1 (f) CC(C)CC(=O)CC(C)C1CC=C(C(=O)O)CC1 (g) OC1CCOC1O (h) CC12CCCCC1CC(=O)CC2

When oxaloacetic acid and acetyl-coenzyme A (acetyl-CoA) labeled with radioactive carbon-14 in position 2 are incubated with citrate synthase, an enzyme of the tricarboxylic acid cycle, only the following enantiomer of [2-14C]citric acid is formed stereoselectively. Note that citric acid containing only \({ }^{12} \mathrm{C}\) is achiral. Assign an \(R\) or \(\$$ configuration to this enantiomer of \)[2-14\( C]citric acid. (Note: Carbon-14 has a higher priority than carbon-12.) O=C(O)CC(O)(CC(=O)O)C(=O)O Oxaloacetic acid Acetyl-CoA \)\left[2^{-14} \mathrm{C}\right]$ Citric acid

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