Structure and synthesis of alcohols | Practice Problems, Examples & Solutions

Introduction

Chemistry : An Introduction to General, Organic, and Biological Chemistry

A student in your class asks you for advice on learning chemistry. Which of the following might you suggest?
a. forming a study group
b. skipping a lecture
c. visiting the professor during office hours
d. waiting until the night before an exam to study
e. being an active learner

Chemistry in Our Lives

Learning Chemistry: A Study Plan

01:37

Chemistry : An Introduction to General, Organic, and Biological Chemistry

Identify each activity, $\mathbf{a}-\mathbf{f},$ as an observation (O), a hypothesis (H) an experiment (E), or a conclusion (C). Lucia wants to develop a process for dyeing shirts so that the color will not fade when the shirt is washed. She proceeds with the following activities:
a. Lucia notices that the dye in a design fades when the shirt is washed.
b. Lucia decides that the dye needs something to help it combine with the fabric.
c. She places a spot of dye on each of four shirts and then places each one separately in water, salt water, vinegar, and baking soda and water.
d. After one hour, all the shirts are removed and washed with a detergent.
e. Lucia notices that the dye has faded on the shirts in water, salt water, and baking soda, while the dye did not fade on the shirt soaked in vinegar.
f. Lucia thinks that the vinegar binds with the dye so it does not fade when the shirt is washed.

Chemistry in Our Lives

Scientific Method: Thinking Like a Scientist

09:29

Chemistry : An Introduction to General, Organic, and Biological Chemistry

Read the labels on products used to wash your dishes. What are the names of some chemicals contained in those products?

Chemistry in Our Lives

Chemistry and Chemicals

Structure and Classification of Alcohols

14 Practice Problems

02:38

Introduction to General, Organic and Biochemistry

Arrange these compounds in order of increasing boiling point. Values in $^{\circ} \mathrm{C}$ are 0,35 , and 97 .
(a) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(b) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{OCH}_{2} \mathrm{CH}_{3}$
(c) $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{3}$

Alcohols, Ethers, and Thiols

05:22

Introduction to General, Organic and Biochemistry

Answer true or false.
(a) The functional group of an alcohol is the $-\mathrm{OH}$ (hydroxyl) group.
(b) The parent name of an alcohol is the name of the longest carbon chain that contains the $-\mathrm{OH}$ group.
(c) A primary alcohol contains one $-$ OH group, and a tertiary alcohol contains three - OH groups.
(d) In the IUPAC system, the presence of three $-$ OH groups is shown by the ending -triol.
(e) A glycol is a compound that contains two $-\mathrm{OH}$ groups. The simplest glycol is ethylene glycol, $\mathrm{HOCH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
(f) Because of the presence of an $-$ OH group, all alcohols are polar compounds.
(g) The boiling points of alcohols increase with in creasing molecular weight.
(h) The solubility of alcohols in water increases with increasing molecular weight.

Alcohols, Ethers, and Thiols

08:00

Organic Chemistry

An unknown alcohol with a molecular formula of $\mathrm{C}_{7} \mathrm{H}_{4} \mathrm{O}$. was oxidized to an aldehyde with $\mathrm{HOCl}$. When an acidic solution of the alcohol was distilled. two alkencs were obtainca. The alkcne formed in graater yicld was determincd to be 1 -mcthylcyclohexcne. The other alkenc formed the original unknown alcohol when treated with BH,/THF followed by H_O_ HO^', and H_O. Identify the unknown alcohol.

Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds

Nomenclature of Alcohols and Phenols

12 Practice Problems

02:52

Introduction to General, Organic and Biochemistry

Both alcohols and phenols contain an - OH group. What structural feature distinguishes these two classes of compounds? Illustrate your answer by drawing the structural formulas of a phenol with six carbon atoms and an alcohol with six carbon atoms.

Alcohols, Ethers, and Thiols

07:43

Organic Chemistry

Give each of the following a systematic name and indicate whether each is a primary, secondary, or tertiary alcohol:

An Introduction to Organic Compounds: Nomenclature, Physical Properties, and Structure

02:46

Organic Chemistry

Give IUPAC names for the following compounds:
a.(FIGURE CAN'T COPY)
b.(FIGURE CAN'T COPY)
c.(FIGURE CAN'T COPY)
d.(FIGURE CAN'T COPY)
e.(FIGURE CAN'T COPY)
f.(FIGURE CAN'T COPY)

Alcohols and Phenols

Physical Properties of Alcohols

11 Practice Problems

02:23

Introduction to General, Organic and Biochemistry

The mechanism of the acid-catalyzed dehydration of an alcohol to an alkene is the reverse of the acidcatalyzed hydration of an alkene. The dehydration mechanism occurs by the following three steps. Step 1: Add a proton. Step 2: Break a bond to form stable molecules or ions. Step 3: Take away a proton. These three steps are illustrated here by the dehydration of 2 -butanol to give 2 -butene. Use curved arrows to show the flow of electrons in each step; that is, show how each bond-making or bond-breaking step occurs.

Alcohols, Ethers, and Thiols

04:32

Introduction to General, Organic and Biochemistry

Draw structural formulas and write common names for the six isomeric ethers with the molecular for mula $\mathrm{C}_{5} \mathrm{H}_{12} \mathrm{O}$.

Alcohols, Ethers, and Thiols

04:20

Introduction to General, Organic and Biochemistry

Following are structural formulas for 1 -butanol and 1-butanethiol. One of these compounds has a boiling point of $98^{\circ} \mathrm{C}$ and the other has a boiling point of $117^{\circ} \mathrm{C} .$ Which compound has which boiling point?
$$\begin{array}{cc}\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH} & \mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{SH} \\1-\text { Butanol } & 1 \text { -Butanethiol }\end{array}$$

Alcohols, Ethers, and Thiols

Commercially Important Alcohols

3 Practice Problems

02:13

Introduction to General, Organic and Biochemistry

Write a balanced equation for the complete combustion of ethanol, the alcohol blended with gasoline to produce E85.

Alcohols, Ethers, and Thiols

02:29

Introduction to General, Organic and Biochemistry

As we will see in Chapter $16,$ the carbonyl group of aldehydes and ketones reacts with water to form a compound called a hydrate. The hydration of a carbonyl group is catalyzed by acid. Formaldehyde, for example, reacts as shown below. When dissolved in water, formaldehyde exists almost entirely as its hydrate. This aqueous solution is given the name formalin.
The mechanism for this acid-catalyzed hydration is similar to the mechanism for the acid-catalyzed hydration of an alkene to give an alcohol and occurs by the following three steps. Step 1: Add a proton. Step 2: Make a new covalent bond between an electrophile (an electron-seeking species) and a nucleophile (an electron-donating species). Step 3: Take a proton away. Write an equation for each step and show by the use of curved arrows how each of these steps occurs. Show all bond-forming steps and bond-breaking steps.

Alcohols, Ethers, and Thiols

Acidity of Alcohols and Phenols

1 Practice Problems

02:03

Organic Chemistry

$p$ -Nitrobenzyl alcohol is more acidic than benzyl alcohol, but $p$ -methoxybenzyl alcohol is less acidic. Explain.

Alcohols and Phenols

Synthesis of Alcohols: Introduction and Review

3 Practice Problems

04:17

Introductory Chemistry

Why is methanol sometimes called wood alcohol? Describe the modern synthesis of methanol. What
are some uses of methanol?

Organic Chemistry

Properties and Uses of Alcohols

09:00

Organic Chemistry

Devise a synthesis of each alcohol from organic alcohols having one or two carbons and any required reagents.

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

02:52

Organic Chemistry

The ether, $CH_3OCH_2CH_3$, can be prepared by two different nucleophilic substitution reactions, one using $CH_3O^-$ as nucleophile and the other using $CH_3CH_2O^-$ as nucleophile. Draw both routes.

Alkyl Halides and Nucleophilic Substitution

Organic Synthesis

Organometallic Reagents for Alcohol Synthesis

3 Practice Problems

01:31

Organic Chemistry

Using any necessary reagents, show how the following compounds could be prepared using ethylene oxide
as one of the reactants: a. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$
b. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{Br}$ c. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{D}$
d. $\mathrm{CH}_{3} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{CH}_{2} \mathrm{OH}$

Organometallic Compounds

00:44

Organic Chemistry

What bromo-substituted compound is required to react with $\left(\mathrm{CH}_{2}=\mathrm{CH}\right)_{2} \mathrm{CuLi}$ in order to form the following compound?

Organometallic Compounds

03:41

Organic Chemistry

Devise three different methods to prepare each compound from benzene: (a) C$_6$H$_5$CH$_2$CH$_2$OH (2-phenylethanol); (b) C$_6$H$_5$COCH$_3$ (acetophenone). You may also use organic compounds that have one or two carbons, and any required inorganic reagents. At least two of the three methods must use a reaction of the organometallic reagents described in this chapter.

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Reactions of Organometallic Compounds

11 Practice Problems

0:00

Inorganic Chemistry

Formal bond orders can sometimes be misleading. For example, $\left[\mathrm{Re}_{2} \mathrm{Cl}_{9}\right]^{-},$ which has a metal-metal bond order of $3.0,$ has a longer $\mathrm{Re}-$ Re bond $(270.4 \mathrm{pm})$ than $\left[\mathrm{Re}_{2} \mathrm{Cl}_{0}\right]^{2-},(247.3 \mathrm{pm}),$ which has a bond order of 2.5 Account for the shorter bond in $\left[\mathrm{Re}_{2} \mathrm{Cl}_{9}\right]^{2-}$ (Hint: see G. A. Heath, J. E. McGrady, R. G. Raptis, A. C. Willis, Inorg. Chem. , 1996 , 35 , 6838.)

Parallels between Main Group and Organometallic Chemistry

05:01

Inorganic Chemistry

Calculations reported on the fragments $\mathrm{Mn}(\mathrm{CO})_{5}$ $\mathrm{Mn}(\mathrm{CO})_{3}, \mathrm{Cu}\left(\mathrm{PH}_{3}\right),$ and $\mathrm{Au}\left(\mathrm{PH}_{3}\right)$ have shown that the
energies of their singly occupied hybrid orbitals are in the order $\operatorname{Au}\left(\mathrm{PH}_{3}\right)>\mathrm{Cu}\left(\mathrm{PH}_{3}\right)>\mathrm{Mn}(\mathrm{CO})_{3}>\mathrm{Mn}(\mathrm{CO})_{5}$
a. In the compound $(\mathrm{OC})_{5} \mathrm{Mn}-\mathrm{Au}\left(\mathrm{PH}_{3}\right),$ would you
expect the electrons in the $\mathrm{Mn}-$ Au bond to be polarized toward Mn or Au? Why? (Hint: sketch an energy-level diagram for the molecular orbital formed between $\mathrm{Mn}$ and $\mathrm{Au.}$.
b. The $\mathrm{Cu}\left(\mathrm{PPh}_{3}\right)$ fragment bonds to $\mathrm{C}_{5} \mathrm{H}_{5}$, in a manner similar to the isolobal $\mathrm{Mn}(\mathrm{CO})_{3}$ fragment. However, the geometry of the corresponding $\mathrm{Au}\left(\mathrm{PPh}_{3}\right)$ complex is significantly different:
Suggest an explanation. (See D. G. Evans, D. M. P. Mingos, J. Organomet. Chem. , 1982 , 232 , 171.)

Parallels between Main Group and Organometallic Chemistry

08:04

Inorganic Chemistry

Propose two organometallic fragments not mentioned in this chapter that are isolobal with
a. $\mathrm{CH}_{3}$
b. $\mathrm{CH}$
c. $\mathrm{CH}_{3}^{+}$
d. $\mathrm{CH}_{3}^{-}$
e. $\left(\eta^{5}-\mathrm{C}_{5} \mathrm{H}_{5}\right) \mathrm{Fe}(\mathrm{CO})_{2}$
f. $\operatorname{Sn}\left(\mathrm{CH}_{3}\right)_{2}$

Parallels between Main Group and Organometallic Chemistry

Side Reactions of Organometallic Reagents: Reduction of Alkyl Halides

3 Practice Problems

00:41

Organic Chemistry

Which of the following alkyl halides could be successfully used to form a Grignard reagent?

Organometallic Compounds

04:37

Organic Chemistry

Draw all stereoisomers formed when each alkene is treated with mCPBA.

Oxidation and Reduction

The Reduction of Polar C-X a Bonds

Reduction of the Carbonyl Group: Synthesis of 1° and 2° Alcohols

4 Practice Problems

04:50

Organic Chemistry

Compelling evidence for the existence of a tetrahedral intermediate in nucleophilic acyl substitution was obtained in a series of elegant experiments carried out by Myron Bender in 1951. The key experiment was the reaction of aqueous $^-$OH with ethyl benzoate (C$_6$H$_5$COOCH$_2$CH$_3$) labeled at the carbonyl oxygen with $^{18}$O. Bender did not allow the hydrolysis to go to completion, and then examined the presence of a label in the $\textit{recovered starting material}$. He found that some of the recovered ethyl benzoate no longer contained a label at the carbonyl oxygen. With reference to the accepted mechanism of nucleophilic acyl substitution, explain how this provides evidence for a tetrahedral intermediate.

Carboxylic Acids and Their DerivativesNucleophilic Acyl Substitution

04:41

Organic Chemistry

What product is formed when (CH_{3})c2=CHCH$_2$COCH$_2$CH$_2$CO$_2$CH$_2$CH$_3$ is treated with each reagent: (a) H$_2$ (1 equiv), Pd-C; (b) H2 (2 equiv), Pd-C; (c) LiAIH_$4$, followed by H$2$O; (d) NaBH$4$, CH$_3$OH?

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

Reduction of Carboxylic Acids and Their Derivatives

04:10

Organic Chemistry

Draw the products formed when CH$_3$COCH$_2$CH$_2$CH=CH$_2$ is treated with each reagent:
(a) LiAIH$\4$, then H$_2$O; (b) NaBH$_4$ in CH$_3$OH; (c) H$_2$ (1 equiv), Pd-C; (d) H2 (excess), Pd-C; (e) NaBH$_4$ (excess) in CH$_3$OH; (f) NaBD$_4$ in CH3OH.

Introduction to Carbonyl Chemistry; Organometallic Reagents; Oxidation and Reduction

The Stereochemistry of Carbonyl Reduction

Thiols (Mercaptans)

5 Practice Problems

03:19

Organic Chemistry

Thiols can be prepared from the reaction of thiourea with an alkyl halide, followed by hydroxide-ion-promoted hydrolysis.
a. Propose a mechanism for the reaction.
b. What thiol would be formed if the alkyl halide employed were pentyl bromide?

Carbonyl Compounds II

01:49

Chemistry : An Introduction to General, Organic, and Biological Chemistry

Classify each of the following according to its functional groups $(s):(12.1,12.3)$
a. BHA, an antioxidant used as a preservative in foods such as baked goods, butter, meats, and snack foods (EQUATION CANNOT COPY)
(IMAGE CANNOT COPY)
b. vanillin, a flavoring, obtained from the seeds of the vanilla bean
(EQUATION CANNOT COPY)
(IMAGE CANNOT COPY)

Alcohols, Thiols, Ethers, Aldehydes, and Ketones

Reactions of Alcohols, Thiols, Aldehydes, and Ketones

04:56

Chemistry : An Introduction to General, Organic, and Biological Chemistry

Draw the condensed structural formula for the organic product formed when each of the following is reduced by hydrogen in the presence of a nickel catalyst:
a. butyraldehyde
b. acetone
c. hexanal
d. 2 -methyl-3-pentanone

Alcohols, Thiols, Ethers, Aldehydes, and Ketones

Reactions of Alcohols, Thiols, Aldehydes, and Ketones

Preparation of alcohols

3 Practice Problems

05:59

Organic Chemistry

Specify the appropriate alkene and reagents for synthesis of each of the following alcohols by hydroboration-oxidation.
(EQUATION CAN'T COPY)

Alkenes and Alkynes II

04:57

Organic Chemistry

Draw the organic product of each reaction and classify the product as an alcohol, symmetrical
ether, or unsymmetrical ether.

Alcohols, Ethers, and Epoxides

Preparation of Alcohols, Ethers, and Epoxides

03:14

Chemistry: Structure and Properties

Ester compounds often have a sweet, pleasant odor. Many characteristic fruit scents are largely due to the natural presence of one or more ester compounds. As such, artificial scents for foods are often composed of complex mixtures of various esters. The exact identity and ratio of ingredients that compose a particular scent are closely guarded secrets in the food and fragrance industry.

Suppose that you are a chemist working for a company that is creating a new line of air fresheners. The company is considering three scents: apple, pear, and pineapple. The project manager has asked you to prepare the ester compounds that are largely responsible for these scents. The structural formulas for these ester compounds are shown here:

To prepare these esters, you have been given the alcohols listed in the table and an adequate supply of all other necessary reagents, solvents, and equipment.

Use the structural formulas of the alcohols and information in the table to answer these questions:
a. Provide a name for each ester that you will prepare.
b. Draw the structure of each alcohol listed in the table.
c. Determine the procedure you will use to prepare each ester, using the reactions found in this chapter. (Hint: Recall that esters are derived from a carboxylic acid and an alcohol.)
d. Calculate the cost to prepare 100.0 g of each ester. Which one will be the most expensive to prepare? Which ester will be the least expensive? (Consider only the cost of the alcohols in the table, and disregard the costs of other reagents. Assume 100% yield for all reactions.)

Organic Chemistry

Protection of alcohols

0 Practice Problems

Preparation of phenols

2 Practice Problems

17:05

Organic Chemistry

Three arene oxides can be obtained from phenanthrene.
a. Draw the structures of the three phenanthrene oxides.
b. Draw the structures of the phenols that can be obtained from each phenanthrene oxide.
c. If a phenanthrene oxide can lead to the formation of more than one phenol, which phenol will be obtained in greater yicld?
d. Which of the three phenanthrene oxides is most likely to be carcinogenic?

Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing Compounds

Substitution, elimination, and oxidation reactions of alcohols

4 Practice Problems

02:51

Organic Chemistry

What alcohols would give the following products on oxidation?
a.(FIGURE CAN'T COPY)
b.(FIGURE CAN'T COPY)
c.(FIGURE CAN'T COPY)

Alcohols and Phenols

05:34

Organic Chemistry

(a) Provide a mechanism for the aldol addition of propanal shown here.
(FIGURE CAN'T COPY)
(b) How can you account for the fact that the product of the aldol addition is 3-hydroxy-2-methylpentanal and not 4-hydroxyhexanal?
(c) What products would be formed if the reaction mixture were heated?

Condensation and Conjugate Addition Reactions of Carbonyl Compounds

07:18

Organic Chemistry

Show how 1-pentanol could be transformed into each of the following compounds. (You may use any needed inorganic reagents and you need not show the synthesis of a particular compound more than once.)
(a) 1 -Bromopentane
(b) 1 -Pentene
(c) 2 -Pentanol
(d) Pentane
(e) 2 -Bromopentane
(f) $1-$ Hexanol
(g) 1 -Heptanol
(h) Pentanal
(i) 2 -Pentanone
(i) Pentanoic acid
(k) Dipentyl ether (two ways)
(1) 1 -Pentyne
(m) 2 -Bromo-1-pentene
(n) Pentyllithium
(o) 4 -Methyl-4-nonanol

Alcohols from Carbonyl Compounds