Schaum's Outline of Organic Chemistry

George Hademenos, George Hademenos

Chapter 19 PHENOLIC COMPOUNDS - all with Video Answers

Educators

Chapter Questions

From readily available phenolic compounds, synthesize the anitoxidant food preservatives $(a)$ BHA (tert-butylatedhydroxyanisole, a mixture of 2- and 3-tert-butyl-4-methoxyphenol; (b) BHT (tert-butylated hydroxytoluene).

Hunza Gilgit

Numerade Educator

02:21

Problem 2

Write a structural formula for the product of the Diels-Alder reaction of $p$-benzoquinone with:

Ian Kaigh

Numerade Educator

03:56

Problem 3

Compared to toluene, phenol $(a)$ has a higher boiling point and $(b)$ is more soluble in $\mathrm{H}_2 \mathrm{O}$. Explain.

Ian Kaigh

Numerade Educator

01:07

Problem 4

Account for the lower boiling point and decreased $\mathrm{H}_2 \mathrm{O}$ solubility of $o$-nitrophenol and $o$ hydroxybenzaldehyde as compared with their $m$ and $p$ isomers.

Narayan Hari

Numerade Educator

01:34

Problem 5

Give a mechanism for the acid-catalyzed rearrangement of cumene hydroperoxide involving an intermediate with an electron-deficient $\mathrm{O}$ (like $\mathrm{R}^{+}$).

George Bennett

Numerade Educator

10:15

Problem 6

Outline reactions and reagents for industrial syntheses of the following from benzene, and naphthalene $(\mathrm{NpH})$ and inorganic reagents: $(a)$ catechol, $(b)$ resorcinol, $(c)$ picric acid $(2,4,6$-trinitrophenol), $(d) \beta$ naphthol $(\beta-\mathrm{NpOH})$.

Nima Gharibi

Numerade Educator

11:02

Problem 7

Devise practical laboratory syntheses of the following phenols from benzene or toluene and any inorganic or aliphatic compounds: (a) m-iodophenol, (b) 3-chloro-4-methylphenol, (c) 2-bromo-4-methylphenol.

Matthew Lueckheide

Numerade Educator

01:01

Problem 8

Why does aqueous $\mathrm{NaHCO}_3$ solution dissolve $\mathrm{RCOOH}$ but not $\mathrm{PhOH}$ ?

Alkendra Singh

Numerade Educator

03:48

Problem 9

What are the effects of $(a)$ electron-attracting and $(b)$ electron-releasing substituents on the acid strength of phenols?

Madeline Currie

Numerade Educator

01:46

Problem 10

In terms of resonance and inductive effects, account for the following relative acidities.
(a) $p-\mathrm{O}_2 \mathrm{NC}_6 \mathrm{H}_4 \mathrm{OH}>m-\mathrm{O}_2 \mathrm{NC}_6 \mathrm{H}_4 \mathrm{OH}>\mathrm{C}_6 \mathrm{H}_5 \mathrm{OH}$
(b) $m-\mathrm{ClC}_6 \mathrm{H}_4 \mathrm{OH}>p-\mathrm{ClC}_6 \mathrm{H}_4 \mathrm{OH}>\mathrm{C}_6 \mathrm{H}_5 \mathrm{OH}$

Hitendra Singh

Numerade Educator

04:36

Problem 11

Assign numbers from 1 for LEAST to 4 for MOST to indicate the relative acid strengths in the following groups: (a) phenol, $m$-chlorophenol, $m$-nitrophenol, $m$-cresol; $(b)$ phenol, benzoic acid, $p$-nitrophenol, carbonic acid; $(c)$ phenol, $p$-chlorophenol, $p$-nitrophenol, $p$-cresol; $(d)$ phenol, $o$-nitrophenol, $m$-nitrophenol, $p$ nitrophenol; $(e)$ phenol, $p$-chlorophenol, 2,4,6-trichlorophenol, 2,4-dichlorophenol; $(f)$ phenol, benzyl alcohol, benzenesulfonic acid, benzoic acid.

Adriano Chikande

Numerade Educator

11:44

Problem 12

Why does cleavage of aryl ethers, ArOR, with $\mathrm{HI}$ yield only ArOH and RI?

Jared Cellini

Numerade Educator

00:58

Problem 13

Phenyl acetate undergoes the Fries rearrangement with $\mathrm{AlCl}_3$ to form ortho- and para hydroxyacetophenone. The ortho isomer is separated from the mixture by its volatility with steam.

Lottie Adams

Numerade Educator

01:19

Problem 14

Outline a mechanism for the $(a)$ Kolbe reaction, $(b)$ Reimer-Tiemann reaction.

Dr. Satish Ingale

Numerade Educator

19:52

Problem 15

Use phenol and any inorganic or aliphatic reagents to synthesize (a) aspirin (acetylsalicyclic acid), (b) oil of wintergreen (methyl salicylate). Do not repeat the synthesis of any compound.

Anupa Sharad Medhekar

Numerade Educator

02:22

Problem 16

Predict the product of the Claisen rearrangement of $(a)$ allyl- $3-{ }^{14} \mathrm{C}$ phenyl ether, $(b)$ 2,6dimethylphenyl allyl- $3-{ }^{14} \mathrm{C}$ ether.

Mikayla Stephens

Numerade Educator

02:47

Problem 17

Name the following compounds:
(a) m-ethoxytoluene,
(b) methylhydroquinone,
(c) p-allylphenol.

Adriano Chikande

Numerade Educator

01:23

Problem 18

Write the structure for (a) phenoxyacetic acid, $(b)$ phenyl acetate, $(c)$ 2-hydroxy-3-phenylbenzoic acid, $(d) p$-phenoxyanisole.

Sima Sarker

Numerade Educator

01:05

Problem 19

Draw a flow sheet for the separation of a mixture of $\mathrm{PhOH}, \mathrm{PhCH}_2 \mathrm{OH}$, and $\mathrm{PhCOOH}$.

David Collins

Numerade Educator

03:34

Problem 20

What product is formed when $p$-cresol is reacted with $(a)\left(\mathrm{CH}_3 \mathrm{CO}\right)_2 \mathrm{O}$, (b) $\mathrm{PhCH}_2 \mathrm{Br}$ and base, (c) aqueous $\mathrm{NaOH},(d)$ aqueous $\mathrm{NAHCO}_3,(e)$ bromine water?

Himanshu Kushwaha

Numerade Educator

05:39

Problem 21

Use simple test tube reactions to distinguish (a) $p$-cresol from $p$-xylene, $(b)$ salicylic acid from aspirin (acetylsalicylic acid).

Katherine Pohly

Numerade Educator

03:08

Problem 22

Identify compounds (A) through (D).

Alkendra Singh

Numerade Educator

11:02

Problem 23

Prepare (a) 2-bromo-4-hydroxytoluene from toluene, (b) 2-hydroxy-5-methylbenzaldehyde from $p$-toluidine, (c) $m$-methoxyaniline from benzenesulfonic acid.

Matthew Lueckheide

Numerade Educator

03:38

Problem 24

Use the Bucherer reaction to prepare $2-(\mathrm{N}$-methyl)- and 2-(N-phenyl)naphthylamines.

Ronald Prasad

Numerade Educator

01:12

Problem 25

(a) Give products, where formed, for reaction of $\mathrm{PhN}_2^{+} \mathrm{Cl}^{-}$with (i) $\alpha$-naphthol, (ii) $\beta$-naphthol, (iii) 4-methyl-1-naphthol, (iv) 1-methyl-2-naphthol. (b) How can these products be used to make the corresponding aminonaphthols?

Alkendra Singh

Numerade Educator

01:01

Problem 27

The acid-base indicator phenolphthalein is made by using anhydrous $\mathrm{ZnCl}_2$ to condense $2 \mathrm{~mol}$ of phenol and one mol of phthalic anhydride by eliminating I mol of $\mathrm{H}_2 \mathrm{O}$. What is its formula?

Aadit Sharma

Numerade Educator

01:13

Problem 28

From phenol prepare $(a) p$-benzoquinone, $(b) p$-benzoquinone dioxime, $(c)$ quinhydrone (a $1: 1$ complex of $p$-benzoquinone and hydroquinone).

Sima Sarker

Numerade Educator

01:18

Problem 30

The ir $\mathrm{OH}$ stretching bands for the three isomeric nitrophenols in $\mathrm{KBr}$ pellets and in dilute $\mathrm{CCl}_4$ solution are identical for the ortho but different for meta and para isomers. Explain.

Lottie Adams

Numerade Educator

05:34

Problem 31

Show all major products for the following reactions:

Temi Ajayi

Numerade Educator

02:38

Problem 32

(a) Compound (A), $\mathrm{C}_7 \mathrm{H}_8 \mathrm{O}$, is insoluble in aqueous $\mathrm{NaHCO}_3$ but dissolves in $\mathrm{NaOH}$. When treated with bromine water, (A) rapidly forms compound (B), $\mathrm{C}_7 \mathrm{H}_5 \mathrm{OBr}_5$. Give structures for (A) and (B). (b) What would (A) have to be if it did not dissolve in $\mathrm{NaOH}$ ?

Alkendra Singh

Numerade Educator

04:04

Problem 33

A compound $\left(\mathrm{C}_{10} \mathrm{H}_{14} \mathrm{O}\right)$ dissolves in $\mathrm{NaOH}$ but not in $\mathrm{NaHCO}_3$ solution. It reacts with $\mathrm{Br}_2$ in water to give $\mathrm{C}_{10} \mathrm{H}_{12} \mathrm{Br}_2 \mathrm{O}$. The ir spectrum shows a broad band at $3520 \mathrm{~cm}^{-1}$ and a strong peak at $830 \mathrm{~cm}^{-1}$. The proton nmr shows: a singlet at $\delta=1.3(9 \mathrm{H})$, a singlet at $\delta=4.9(1 \mathrm{H})$, a multiplet at $\delta=7.0(4 \mathrm{H})$. Give the structure of the compound.

Ian Kaigh

Numerade Educator

Problem 34

a very toxic compound is a by-product of the manufacture of 2,4,5-trichlorophenol by treating 1,2,4,5-tetrachlorobenzene with $\mathrm{NaOH}$. Suggest a mechanism for the formation of dioxin.

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