1. Draw the structures of the aromatic compounds derived from benzene (Ph-G) below and answer: (a) Draw the resonance structures for compounds in which the substituent group (-G) participates in resonance as a ē donor to the aromatic ring or ē withdrawr (acceptor) from the aromatic ring. (b) Discuss the electronic effect of each substituent group, i.e., whether -G has an inductive effect and/or resonance effect on the aromatic ring and whether this effect is an electron donor or electron withdrawer (acceptor). (c) Considering a SEAr reaction, classify each substituent group (-G) according to relative reactivity (in relation to benzene), i.e., whether -G is activating or deactivating. (d) Considering a SEAr reaction, classify each substituent group (-G) according to regioselectivity (ortho, meta, para orientation pattern), i.e., whether-G is ortho/para orienting or meta orienting. Substituent group (-G) -NH2 (amine), Aromatic compound (Ph-G) aniline (amino-benzene) Eph. Ind. Ef. Res. Reat. Orient. -OH (hydroxyl) -OCH3 (methoxyl) -NHCOCH3 (amide) -OCOCH3 (ester) -CH3 (methyl) -Ph -F (fluorine) -CI (chlorine) -Br (bromine) -I (iodine) -CHO (aldehyde) -CONH2 (amide) -CO2CH3 (ester) --CO2H (carboxylic acid) -COCH3 (ketone) --SO3H (sulfonic acid)__ -CN (nitrile) -NO2 (nitro) -CF3 (trifluoro-methyl) -N(CH3)3 (trimethyl-amino) phenol (hydroxy-benzene) anisole (methoxy-benzene) acetanilide (N-phenyl-acetamide) phenyl acetate (phenyl ethanoate) toluene (methyl-benzene) biphenyl (phenylbenzene) fluorine-benzene chloro-benzene bromo-benzene iodine-benzene benzaldehyde (benzoic aldehyde) benzamide (benzoic amide) methyl benzoate benzoic acid acetophenone benzenesulfonic acid benzonitrila nitro-benzene trifluoro-methyl-benzene withdrawer donor activating ortho/para withdrawer withdrawer deactivating meta withdrawer по deactivating meta N,N,N-trimethylanilinium cation

Chemistry
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ISBN:9781305957404
Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
Chapter1: Chemical Foundations
Section: Chapter Questions
Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...
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1. Draw the structures of the aromatic compounds derived from benzene (Ph-G) below and answer:
(a) Draw the resonance structures for compounds in which the substituent group (-G) participates in
resonance as a ē donor to the aromatic ring or ē withdrawr (acceptor) from the aromatic ring.
(b) Discuss the electronic effect of each substituent group, i.e., whether -G has an inductive effect and/or resonance
effect on the aromatic ring and whether this effect is an electron donor or electron withdrawer (acceptor).
(c) Considering a SEAr reaction, classify each substituent group (-G) according to relative reactivity (in relation
to benzene), i.e., whether -G is activating or deactivating.
(d) Considering a SEAr reaction, classify each substituent group (-G) according to regioselectivity (ortho,
meta, para orientation pattern), i.e., whether-G is ortho/para orienting or meta orienting.
Substituent group (-G)
-NH2 (amine),
Aromatic compound (Ph-G)
aniline (amino-benzene)
Eph. Ind. Ef. Res.
Reat.
Orient.
-OH (hydroxyl)
-OCH3 (methoxyl)
-NHCOCH3 (amide)
-OCOCH3 (ester)
-CH3 (methyl)
-Ph
-F (fluorine)
-CI (chlorine)
-Br (bromine)
-I (iodine)
-CHO (aldehyde)
-CONH2 (amide)
-CO2CH3 (ester)
--CO2H (carboxylic acid)
-COCH3 (ketone)
--SO3H (sulfonic acid)__
-CN (nitrile)
-NO2 (nitro)
-CF3 (trifluoro-methyl)
-N(CH3)3 (trimethyl-amino)
phenol (hydroxy-benzene)
anisole (methoxy-benzene)
acetanilide (N-phenyl-acetamide)
phenyl acetate (phenyl ethanoate)
toluene (methyl-benzene)
biphenyl (phenylbenzene)
fluorine-benzene
chloro-benzene
bromo-benzene
iodine-benzene
benzaldehyde (benzoic aldehyde)
benzamide (benzoic amide)
methyl benzoate
benzoic acid
acetophenone
benzenesulfonic acid
benzonitrila
nitro-benzene
trifluoro-methyl-benzene
withdrawer
donor
activating ortho/para
withdrawer withdrawer deactivating
meta
withdrawer
по
deactivating
meta
N,N,N-trimethylanilinium cation
Transcribed Image Text:1. Draw the structures of the aromatic compounds derived from benzene (Ph-G) below and answer: (a) Draw the resonance structures for compounds in which the substituent group (-G) participates in resonance as a ē donor to the aromatic ring or ē withdrawr (acceptor) from the aromatic ring. (b) Discuss the electronic effect of each substituent group, i.e., whether -G has an inductive effect and/or resonance effect on the aromatic ring and whether this effect is an electron donor or electron withdrawer (acceptor). (c) Considering a SEAr reaction, classify each substituent group (-G) according to relative reactivity (in relation to benzene), i.e., whether -G is activating or deactivating. (d) Considering a SEAr reaction, classify each substituent group (-G) according to regioselectivity (ortho, meta, para orientation pattern), i.e., whether-G is ortho/para orienting or meta orienting. Substituent group (-G) -NH2 (amine), Aromatic compound (Ph-G) aniline (amino-benzene) Eph. Ind. Ef. Res. Reat. Orient. -OH (hydroxyl) -OCH3 (methoxyl) -NHCOCH3 (amide) -OCOCH3 (ester) -CH3 (methyl) -Ph -F (fluorine) -CI (chlorine) -Br (bromine) -I (iodine) -CHO (aldehyde) -CONH2 (amide) -CO2CH3 (ester) --CO2H (carboxylic acid) -COCH3 (ketone) --SO3H (sulfonic acid)__ -CN (nitrile) -NO2 (nitro) -CF3 (trifluoro-methyl) -N(CH3)3 (trimethyl-amino) phenol (hydroxy-benzene) anisole (methoxy-benzene) acetanilide (N-phenyl-acetamide) phenyl acetate (phenyl ethanoate) toluene (methyl-benzene) biphenyl (phenylbenzene) fluorine-benzene chloro-benzene bromo-benzene iodine-benzene benzaldehyde (benzoic aldehyde) benzamide (benzoic amide) methyl benzoate benzoic acid acetophenone benzenesulfonic acid benzonitrila nitro-benzene trifluoro-methyl-benzene withdrawer donor activating ortho/para withdrawer withdrawer deactivating meta withdrawer по deactivating meta N,N,N-trimethylanilinium cation
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