DAT Question of the Day

Correct Answer: D. 4

Aromatic compounds are named as derivatives of benzene. Substituents positions are indicated by numbers except that o- (ortho), m- (meta) and p- (para) may be used in place of 1,2-, 1,3-, and 1,4-, respectively, when only two substituents are present. If alkyl substituents are smaller than the ring (6 or fewer carbons), the compound is considered an alkyl substituted benzene. Alkyl substituents larger than the ring (7 or more carbons), are phenyl-substituted alkanes. Compounds are named by numbering the position of each so that the lowest possible numbers are used. The substituents are listed alphabetically when writing the name.

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Correct Answer: A. 3 > 4 > 2 > 5 > 1

There are two main electronic effects that substituents can exert: RESONANCE effects include electron donating (e.g. -OMe) where p electrons are pushed toward the arene or electron withdrawing (e.g. -C=O) where p electrons are drawn away from the arene. INDUCTIVE effects include electronegativity type effects. These too can be either electron donating (e.g. -Me) where s electrons are pushed toward the arene or electron withdrawing (e.g. -CF3, -NR3) where s electrons are drawn away from the arene.

Some general pointers for recognizing the substituent effects:

• The H atom is the standard and is regarded as having no effect.
• Activating groups increase the rate (3 > 4)
• Deactivating groups decrease the rate (5 > 1)

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Correct Answer: C. III

The carbon-chlorine bonds are polar due to the difference in electronegativities of C (2.55) and Cl (3.16) atoms. These individual dipole moments cancel each other out only in an anti-periplanar arrangement (compound III).

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