Solution manual for organic and biochemistry for today 8th edition seager slabaugh 1133605141 978113

Solution Manual for Organic and Biochemistryfor Today 8th Edition Seager Slabaugh 11336051419781133605140

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Chapter 2: Unsaturated Hydrocarbons

CHAPTER OUTLINE

12.1 The Nomenclature of 12.5 Alkynes Alkenes 12.6 Aromatic Compounds and

12 2 The Geometry of Alkenes the Benzene Structure

12 3 Properties of Alkenes 12.7 The Nomenclature of 12.4 Addition Polymers Benzene Derivatives

LEARNING OBJECTIVES/ASSESSMENT

12.8 Properties and Uses of Aromatic Compounds

When you have completed your study of this chapter, you should be able to:

1 Classify unsaturated hydrocarbons as alkenes, alkynes, or aromatics (Section 12 1; Exercise 12 2)

2 Write the IUPAC names of alkenes from their molecular structures. (Section 12 1; Exercise 12 4)

3 Predict the existence of geometric (cis-trans) isomers from formulas of compounds (Section 12 2; Exercise 12 18)

4. Write the names and structural formulas for geometric isomers. (Section 12.2; Exercise 12.20)

5 Write equations for addition reactions of alkenes, and use Markovnikov’s rule to predict the major products of certain reactions. (Section 12 3; Exercise 12 26)

6 Write equations for addition polymerization, and list uses for addition polymers. (Section 12 4; Exercise 12 36)

7. Write the IUPAC names of alkynes from their molecular structures. (Section 12.5; Exercise 12.44)

8. Classify organic compounds as aliphatic or aromatic. (Section 12.6; Exercise 12.48)

9. Name and draw structural formulas for aromatic compounds. (Section 12.7; Exercises 12.52 and 12 54)

10. Recognize uses for specific aromatic compounds. (Section 12.8; Exercise 12.66)

LECTURE HINTS AND SUGGESTIONS

1 Explain the term "unsaturated" as the ability of a hydrocarbon to pick up smaller molecules. Describe how smaller molecules can be added to the double bond. The students have heard of the term "unsaturated" as it applies to fats Explain that unsaturated fats have double bonds as part of their structure.

2. Use molecular models in class to illustrate the different types of isomerism. Students are easily confused as to when structures are equivalent or non-equivalent. Models are essential at this point to illustrate the differences. Two models which represent equivalent rather than isomeric structures can be shown to superimpose upon turning or upon rotation about single bonds.

3. When explaining the formation of addition polymers, first show with structural formulas how ethylene changes into polyethylene. Then show how by replacing one or more hydrogens in the ethylene with another group (e.g., chlorine, a benzene ring), essentially the same reaction can lead to a variety of different polymers. In each case be sure to give common examples of uses for the polymer

SOLUTIONS FOR THE END OF CHAPTER EXERCISES

THE NOMENCLATURE OF ALKENES (SECTION 12.1) AND ALKYNES (SECTION 12.5) 12.1 An unsaturated hydrocarbon is a hydrocarbon containing one or more multiple bonds. 287

288 Chapter 2 3

 12.2 An alkene is a hydrocarbon that contains at least one carbon-carbon double bond. An alkyne is a hydrocarbon that contains at least one carbon-carbon triple bond. An aromatic hydrocarbon is a compound that contains a benzene ring or other similar feature.

12.3 a CH3 CH2 CH3 saturated

b. CH3CH=CHCH3 unsaturated alkene

c. H C C CH CH3

CH3

d.

 12.4

unsaturated alkyne

unsaturated alkene

e. CH3 saturated

f. CH CH2

g. CH CH

CH2 CH2

unsaturated alkene

unsaturated alkene

h. CH2=CHCH2CH3 unsaturated alkene

i. CH3 CHCH3

CH3

a. CH3CH=CHCH3

saturated

e. Br 2-butene

CH3CHCH2 C C CH CH3

b. CH3CH2 C CHCH3

CH3

CH2CH3 6-bromo-2-methyl-3-heptyne 3-ethyl-2-pentene

c. CH3 f. CH

CH3 C C C CH2CH3

CH3

4,4-dimethyl-2-hexyne

d. CH3

CH3 CH2CH3

1-ethyl-2,3-dimethylcyclopropene

g. CH3

CH3CH CH CHCH2CH CH2

6-methyl-1,4-heptadiene 4-methylcyclopentene

12.5

a. CH 3 CHCH CHCH2CH3

CH3

2-methyl-3-hexene

b. CH3CH CHCH CHCHCH3

c. CH3

6-methyl-2,4-heptadiene

Unsaturated Hydrocarbons 289

f. CH2CH2CH3

7-propyl-1,3,5-cycloheptatriene

g. CH2CH2CH2CH3 cyclopentene

CH 2 C CH CH CHCH2CH3

CH2CH3

2-butyl-3-ethyl-1,4-heptadiene

d. CH3 C≡C CH2CH3 2-pentyne

e. CH

3

CH2CHCH3

CH3

3-isobutyl-5-methylcyclohexene

12.6 a 3-ethyl-2-hexene

b. 3,4-dimethyl-1-pentene

CH3 CH3

CH2 CH CH CH CH3

c 3-methyl-1,3-pentadiene CH3

CH2 CH C CH CH3

d 2-isopropyl-4-methylcyclohexene CH3

CH3

CH

CH3

e. 1-butylcyclopropene CH2CH2CH2CH3

290 Chapter 2

12.7 a 4,4,5-trimethyl-2-heptyne

CH3

CH3 C C C CH CH2 CH3

CH3 CH3

b. 1,3-cyclohexadiene

c 2-t-butyl-4,4-dimethyl-1-pentene CH3

CH3 C CH3 CH3

CH2 C CH2 C CH3

CH3

d 4-isopropyl-3,3-dimethyl-1,5-octadiene CH3

CH3 CH CH3

CH2 CH C CH

CH

CH

CH2

CH3

CH3

e. 2-methyl-1,3-cyclopentadiene

CH3

f. 3-sec-butyl-3-t-butyl-1-heptyne CH3

CH3 C CH3

CH C C CH2 CH2 CH2 CH3

CH3 CH CH2CH3

CH3

CH C CH CH3

3-methyl-1-butyne

CH

58 2 C CH CH2 CH3 CH CH C CH CH

b. C H 3 3 diene 1,2-pentadiene 2,3-pentadiene

CH2 CH CH CH CH3 CH2 CH CH2 CH CH2 1,3-pentadiene 1,4-pentadiene

CH3

5 8 c. C H cyclic alkene CH2 C C CH3

3-methyl-1,2-butadiene CH2CH3

1-ethylcyclopropene 3-ethylcyclopropene 1,2-dimethylcyclopropene

CH3

CH3

CH3 CH3

CH3

1,3-dimethylcyclopropene 3,3-dimethylcyclopropene 1-methylcyclobutene

CH3

CH3

CH3

3-methyl-1-pentene

3-methylcyclobutene cyclopentene

CH3

CH2 CH CH2 CH CH3

4-methyl-1-pentene

CH3

CH3

CH3 C CH CH2 CH3

2-methyl-2-pentene

CH3

CH3 CH C CH2 CH3 CH3 CH CH CH CH3

3-methyl-2-pentene

CH2CH3

CH 2 C CH2 CH3

2-ethyl-1-butene

CH3

CH2 CH C CH3 CH3

4-methyl-2-pentene

CH3 CH3

CH2 C CH CH 3

2,3-dimethyl-1-butene

CH3 CH3

CH3 C C CH3

2,3-dimethyl-2-butene

CH3C CHCH2CH2C CHCH2CH CCH 3,7,11-trimethyl-1,3,6,10-dodecatetraene

12.11a. incorrect = 3-pentene

b. incorrect = 3-methyl-2-butene

c. incorrect = 2-ethyl-3-pentyne

12.12a. incorrect =

b. incorrect = 3,5-heptadiene

3 CH2 CH CH CH CH CH3

corrected = 2,4-heptadiene 7 1

c. incorrect = 4-methylcyclobutene 4 1

corrected = 3-methylcyclobutene 3 2

THE GEOMETRY OF ALKENES (SECTION 12.2)

12.13 Carbon atoms in a double bond each have 3 sp2 hybrid orbitals as well 1 unhybridized p orbital.

12.14 Pi bonds are formed when unhybridized p orbitals overlap sideways. The pi bond is represented by . The pi bond contains 2 electrons.

12.15 Carbon atoms in a double bond have a trigonal planar geometry where the two atoms attached to the double bonded carbon atom as well as the other carbon atom in the double bond are in the same plane, separated by bond angles of 120°.

12 16 Structural isomers have a different order of linkage of atoms. Geometric isomers have the same order of linkage of atoms; however, the three dimensional structures are unique because of restricted rotation as a result of a ring or a double bond.

12.17a. Alkenes that do notCH2 CH CH2 CH2 CH3 show geometric 1-pentene

isomerism. There CH2 C CH2 CH3 are four

compounds.

12.18

b. Alkenes that do show geometric isomerism There is one cis- and one trans- compound.

3

c. CH CH C CHCH CH 3 2 3; no geometric isomers

12 19 a CH3CH2CH2CH=CHCH2CH2CH3

b. no geometric isomers (2 –CH2CH3 groups attached to one of the double bond carbon atoms)

c.

 12.20 a. H H b. CH3CH2 H C C C C

CH 2

12.21

PROPERTIES OF ALKENES (SECTION 12.3)

12.22 Alkenes and alkanes are both nonpolar molecules that have low solubility in water and high solubility in nonpolar solvents. They are also less dense than water.

12 23a. A2 + C3H6 → C3H6A2 addition

b. A2 + C3H6 → C3H5A + HA not addition (substitution)

c. HA + C4H8 → C4H9A

d 3O2+C2H4→2CO2+H2O addition not addition (combustion)

e C7H16 → C7H8 + 4 H2 not addition (decomposition)

12.24 Markovnikov’s rule states that when a heteroatomic compound containing hydrogen is added to a multiple bond, the hydrogen will attach to the carbon atom in the multiple bond that is directly bonded to more hydrogen atoms The following reaction is an example of this rule:

 12 26 a.

12.27a.

12.28

a. To prepare 3,4-dibromohexane from 3-hexene, I would use Br2.

b. To prepare hexane from 3-hexene, I would use hydrogen gas and a platinum catalyst

c. To prepare 3-chlorohexane from 3-hexene, I would use HCl.

d. To prepare 3-hydroxyhexane (3-hexanol) from 3-hexene, I would use water and a sulfuric acid catalyst.

12 29 An important commercial application of hydrogenation is the hydrogenation of liquid vegetable oils to produce a solid vegetable shortening.

12.30 Adding reddish-brown bromine to cyclohexane will produce a reddish-brown solution. Adding reddish-brown bromine to 2-hexene will produce a clear solution in a very short time, since the alkene undergoes an addition reaction The differences in the chemical reactivity of these substances will allow them to be differentiated

12

ADDITION POLYMERS (SECTION 12.4)

12.32

A monomer is the starting material for a polymer. It can be a small molecule.

A polymer is a large molecule made up of repeating units (often thousands of repeating units).

An addition polymer is a polymer formed by the reaction of monomers that contained multiple bonds to form the repeating units of a polymer.

A copolymer is a polymer formed by the reaction of at least two different types of monomers.

12

12 34 All of the monomers in Table 12 3 contain one carbon-carbon double bond

12 35

12 37a Styrofoam Food coolers, drinking cups, insulation

b. Acrilan Carpets, fabrics

c. Plexiglass Airplane windows, paint, contact lenses, fiber optics

d PVC Synthetic leather, floor tiles, garden hoses, water pipe

e polypropylene Carpet fiber, pipes, bottles, artificial turf

ALKYNES (SECTION 12.5)

12 38

Each carbon atom bonded with a triple bond has two sp hybrid orbitals

12 39 A triple bond of an alkyne is composed of 1 sigma and two pi bonds

12 40 The geometry of a triple bond is linear.

12 41 Geometric isomerism is not possible in alkynes because the geometry around a triple bond is linear. Each carbon atom in the triple bond only has one other attached group, unlike each carbon atom in a double bond which has two attached groups.

12 42 Acetylene is the simplest alkyne and it is used in torches for welding steel and in making plastics and synthetic fibers

12.43 Alkynes are insoluble in water, are less dense than water, have relatively low melting and boiling points, and are flammable. They undergo addition reactions, like alkenes, but consume twice as much addition reagent for the reaction to go to completion.

12 44 CH C CH2 CH2 CH3CH3 C C CH2 CH3 1-pentyne 2-pentyne

CH3

CH C CH CH3 3-methyl-1-butyne

AROMATIC COMPOUNDS AND THE BENZENE STRUCTURE (SECTION 12.6)

12 45 Carbon atoms in a benzene ring have 3 sp2 hybridized orbitals as well as one unhybridized p orbital and each carbon atom forms 3 sigma bonds.

12.46 The pi bonding in a benzene ring is the result of unhybridized p orbitals overlapping to form a delocalized system.

12 47 The circle within the hexagon represents the evenly distributed electrons in the pi lobes of the six carbon atoms in the benzene ring in the structural formula for benzene.



12 48 Aromatic means a molecule contains a benzene ring or one of its structural relatives

Aliphatic means a molecule does not contain a benzene ring or one of its structural relatives

12.49 Limonene does not contain a benzene ring; therefore, it is not considered aromatic. Aromaticity reflects structure, not the physical property of fragrance

12 50

a. cis-1,2- dibromohexane trans-1,2-dibromohexane Br Br Br Br Dibromocyclohexane is not a planar molecule. Each carbon atom has two attached groups (H or another atom) in addition to two positions of

attachment in the ring In order to maintain a tetrahedral geometry around the carbon atoms, the attached groups can be “above” or “below” the ring Consequently, the molecule can exhibit cis-trans isomerism when it has two attached groups (other than hydrogen) on two different carbon atoms in the ring.

b. 1,2-dibromobenzene is a planar molecule because each carbon atom in the ring is only bonded to 3 other atoms. Consequently, the attached bromine atoms cannot be “above” or “below” the plane of the molecule. This in turn means the molecule cannot exhibit cistrans isomerism

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Antique oak: Raw sienna properly thinned, with a little burnt umber and black added.

4. Spirit Stains.

Black: Alcohol and aniline black.

Mahogany: Alcohol and Bismark brown.

Aniline stains cut with alcohol, and mixed with white shellac and banana oil or amyl alcohol in equal parts make good stains for small pieces of work.

APPENDIX III.

W D.

A working drawing of an object consists of one or more views of that object so drawn that they make known the size, shape, kind of material, etc.

F. 1.

A working drawing differs from a perspective. The former represents an object as it really is, the second, represents the object as it appears. Fig. 1.

F. 2.

1. Instruments.

—Special instruments are required for the making of a mechanical drawing. Fig. 2 shows a drawingboard with paper fastened to it, also a T-square and the two triangles. A compass is needed for drawing circles and arcs of circles.

The T-square is used for drawing horizontal lines. The head must be held firmly against the edge of the board and the lines drawn from left to right. Vertical and oblique lines are drawn from the T-square upward, the triangles being held against the edge of the T-square which, at the same time, is held against the edge of the board.

2. Conventions.

—Since it would be impossible to make full-sized drawings of some objects—a house for instance —it is customary to use a scale and by means of it make a smaller drawing, which shall have all of its parts properly proportioned. For example, if a drawing has printed upon it “¹⁄₂ inch = 1 inch,” it means for every inch of the object the drawing is but one-half an inch. The scale is to be used for measuring only. There is quite a variety of scales. Whatever scale is used, the numbers placed upon the drawing must represent the size of the object and not of the drawing.

In Fig. 3 is shown a mechanical drawing of a common wood spool. It will be seen that there are different kinds of lines. Each has its meaning, as follows:

Light line—For penciling and cross-hatching.

Full line—For visible outlines of objects and limits of parts.

Heavy line—For border lines.

Dot line—For invisible outlines of objects and limits of invisible parts. Same width as 2.

Dash line—For projection lines. Same width as 1.

Long dash line—For dimension lines. Same width as 1.

Dot-and-dash line—For center lines and section lines. Same width as 1.

When there is not room for the figures that represent dimensions, the arrow heads may be turned in the direction of the measurement and placed outside. The figure, too, may be placed outside if necessary.

Nothing but the letters, the figures and the barbs—not the shafts— of the arrow are drawn free-hand.

Sometimes, it is desirable to have one dimension shorter than the scale selected would allow; this is done by means of a broken view: Fig. 4. The figured dimension prevents confusion.

F 5

F 4

F. 6.

In Fig. 5, is shown a sectional drawing. Sectional drawings represent an object as it would appear if cut, with the part nearer the worker removed. Sections are indicated by “cross hatching,” the lines being equally spaced and drawn at an angle of 45 degrees.

Screws and nails are represented as in Fig. 6.

F. 7.

3. Projection and Relation of Views.

—The names and the relative positions of three views are shown in Fig. 7. From these it will be seen (1) that the different views are arranged with reference to the front view, so that the part of a side view which is nearest the front view represents a part of the front of the object, (2) that the corresponding horizontal measurements of top and front views are alike, (3) that the corresponding vertical measurements of front and side views are alike, (4) that the corresponding vertical measurements of the top view and horizontal measurements of a side view are alike.

4. Letters and Figures.

—Letters are usually made freehand, light ruled lines at the top and bottom acting as guides. A simple style of letter and figure is shown in Fig. 8. They are

placed in spaces that the proportion of the parts may the more readily be seen. They may be narrowed or widened by changing the width of the spaces, and shortened or lengthened by changing the height of the spacer.

5. Constructions.

—The hexagon, or six-sided figure; the octagon, or eight-sided figure; and the ellipse are so very frequently used in simple woodwork, that their construction is given here.

F. 8.

F. 9.

Directions for hexagon, Fig. 9: Describe a circle of a size equal to the required distance of hexagon from corner to corner. Draw the diameter A-B. With the point A as a center, using the radius of the circle, cut the circle at 1 and 2. With B as a center, and the same radius, cut the circle at 3 and 4. Connect A-1, A-2, 2-3, etc. Connecting every other point, as A-3, 2-B, etc., makes a six-pointed star.

F. 10.

Directions for octagon, Fig. 10: Draw a square with a width equal to the desired width of the octagon from side to side. Draw the diagonals. With the points A, B, C, and D as centers and a radius equal to one-half the diagonal, cut the sides of the square at 1, 2, 3, 4, 5, 6, 7, 8. Connect these points as shown.

F 11

Directions for ellipse, Fig. 11: An ellipse is a curve such that the sum of the distances from any point on it to two fixed points called the focii shall always be the same.

An easy way to construct such a curve is to place two thumb tacks at the focii, attach the ends of a string to them. With a pencil moving freely in the string but holding it taut draw the curve. By moving the tacks farther apart or closer together and by lengthening or shortening the string, the size and shape of the curve may be changed as desired.

F. 13.

6. Order of Procedure.

—Beginners should strive to know and to acquire good practice in drawing. Before beginning see that the pencil is properly sharpened.

(1) Determine the size and spacings of the views so that the parts of the drawings may be properly placed.

(2) With light full lines block out the different views. Blocking-out lines are made of indefinite length and the proper distances marked off on them after they are drawn. Holding the rule or scale upon the drawing vertically, mark off the vertical spaces. Draw light lines thru these points. Upon one of these horizontal lines lay off the horizontal spaces. Draw light vertical lines thru these points. Fig. 12.

(3) Put on the dimensions.

(4) Put on the lettering.

(5) The drawing is ready for inking. In blocking-out, all lines are made full, light. In inking, the different kinds must be represented properly. Fig. 13. If it is not to be inked go over the lines that

represent edges with the pencil a second time so that the outlines of the object will “stand out.”

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A convenient collection of good problems ready to place in the hands of the pupils. It consists of forty plates bound in heavy paper covers with brass fasteners. Each plate is a working drawing, or problem in bench work that has been successfully worked out by boys in one of the grades from seven to nine inclusive. Many of the problems can be worked out in various ways according to the individual ability, interest and taste of the pupil. Price, 75 cents. Board covers, 20 cents extra.

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Problems in Mechanical Drawing. By CHARLES A.

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This book consists of 80 plates and a few explanatory notes, and is bound in heavy paper covers with brass fasteners Its purpose is to furnish teachers of classes beginning mechanical drawing with a large number of simple, practical problems These have been selected with reference to the formation of good habits in technique, the interest of the pupils, and the subjects usually included in a grammar and first-year high school course. The book covers simple projection straight lines and circles, problems involving tangents, planes of projection, revolution of solids, developments, intersections, isometric projection, lettering and working drawings. Each problem given is unsolved and therefore in proper form to hand to the pupil for solution.

Price, $1.00. Board covers, 20 cents extra.

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The Wash Method of Handling Water Colour.

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Transcriber’s Notes

Inconsistent hyphenation and spelling have been retained except as mentioned under Changes made below.

If supported by the hard- and software used to read this text, most illustrations may be enlarged by opening them in a new window or tab.

Page 35, ... being careful to hold so as to get the full benefit ...: part of the sentence appears to be missing.

Page 79, Paragraph starting The gage of wire for nails and the gage of wire for screws ...: the size of Figs. 132 and 135 in this text depend on the display used, and are, of course, not necessarily displayed in their true size.

Pages 132-133: Figs. 214 and 213 appear in reverse order in the source document.

Page 146, paragraph starting Hickory excels as carriage and wagon stock ...: the repeated paragraph is also repeated in the source document; ... giving rise to “curly” and blister” figures ...: should be either “curly and blister” or “curly” and “blister”.

Page 156, Wood stains are cheap ...: possibly an error for Water stains are cheap ....

Changes made

Several obvious minor typographical errors have been corrected silently. Some punctuation inconsistencies in illustration captions and references have been standardised.

Texts in a dashed box

does not occur as text in the source document; but has been transcribed from the accompanying illustration.

Captions with Figs. 95, 119, 193: dashes have been added to some of the entries for consistency.

Page 9: heading PART I. TOOLS AND ELEMENTARY PROCESSES. has been inserted cf. the Table of Contents.

Page 43: A True and smooth ... has been replaced with 1. True and smooth ....

Page 98: ... Chapter I, Sec-1 ... has been changed to ... Chapter I, Section 1 ....

Page 116: PART THREE has been changed to PART III for consistency.

Page 138: dicotyledon has been changed to dicotyledons.

Page 171: bicromate has been changed to bichromate.

WOODWORKING

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