Ch5 - S olutions Chapter 4 Acids and Bases Problem 4 53...

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99 Solutions Chapter 5: Alkenes: Bonding, Nomenclature, and Properties CHAPTERS Solutions to the Problems Problem 5.1 Calculate the index of hydrogen deficiency of cyclohexene, C6HlO' and account for this deficiency by reference to its structural formula. The molecular formula of the reference acyclic alkane of six carbens is ~6HI.4' The ind~x of hydrogen . deficiency of cyclohexane (14.10)12 = 2 and is accounted for by the combmatlOn of one rIng and one n bond In cyclohexene. o Cyclohexene Problem 5.2 The index of hydrogen deficiency of niacin is 5. Account for this index of hydrogen deficiency by reference 10 the structural formula ofniacin. Nicotinamide (Niacin) The index of hydroge'n deficiency of 5 can be accounted for by the presence ~f the ring plus the three nbonds in the ring, as well as the n, bond of the carbonyl group. Emblem 5.3 Write the IUPAC name of each alkane. (a) ~ (b) >=< ~ /H C=C ,,/ CH 3 / H CH I CH 3 3.Methyl.l.butene 2,3·Dimethyl·2·butene Problem 5.4 Which alkenes show cis, trans isomerism? For each alkene that does, draw the trans isomer. (a) 2-Pentene (b) 2-Methyl-2-pentene (c) 3-Methyl-2-pentene CH3CH?o. . H No cis/trailS isomers . -, / because there are two /C=C, methyl groups on one CH 3 ' C?H 3 end of the double bond tralls-3·Methyl·2·pentene trans-2-Pentene Problem 5.5 Name each alkene and specify its configuration by the E-Z system. r, 5 , . ' CI~' CI~ (!O)i.~. (b) (a) ~ Br (Z)-I.Bromo·l.chloropropene . (E)·2,3,4· Trimethyl·3·heptene (E)-I-Chloro·2,3·dimethyl- '2·pentene
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100 Solutions Chapter 5: Alkenes: Bonding. Nomenclature, and Properties Problem 5.6 Write the. IUPAC na~e of each cycloalkene (a) IblQ .(0 1 0-+-. 1,3-Dimethyl- Cyclooctene 4-(I,I-DimethyJethyl)- cyclopentene cyclohexene (IUPAC) 4-tert-Butylcyclohexene (Common) Problem 5.7 Draw structUral formulas for the other two stereoisomers of 2,4-heptadiene. 6 7 '1 H,4 5/ CH 2 CH 3 H 3 C,2 . 3/C C, /C=C, H H H cis,trails- 2;4-Heptadiene Cis,cis-2,4-Hept;ldiene . Problem 5.8 (JOE, 12Z)-10,i2-hexadecadiene-l-ol is a sex pheromone of the silkworm. Draw a structural formula for this compound. Structure of Alkenes Problem 5.9 Predict all ~pproximate bon~ angles about each highlighted carbon atom. To make these predictions, use valence shell electron-paIr repulSIOn (SectIon 1.4). '. ,109.5° ~ ... (a) ~ (b) GCH,OH . 0 Ie) Q40H 101 . Solutions Chapter 5: Alkenes: Bon~,ing, Nomenclature. and Properties Problem 5.10 For each highlighted carbon atom in Problem 5.9, i~entify which atomic orbitals are used to form each 0 bond and which are used to form each 1t bond. Each bond is labeled 0 or 1t and the orbitals overlapping to form each bond are shown. .Osp3_ ~/ 0sp3-Sp3 .0S{l~sp3 ./dt 1s 1t' ~S{I-sp3 (b)' CH:20H (·a) 2~2p (1 ....2 \.. i-
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Ch5 - S olutions Chapter 4 Acids and Bases Problem 4 53...

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