Homework assignment for Chapter 22: 29, 30, 32, 34, 35, 36, 42, 44, 45, 46, 47, 48, 51, 52, 53, 57, 65, STY: 1-2, 4-5, 7-9, 11, 13.

Key to Chapter 22

22.29 (a) same, (b) constitutional isomer, (c) same, (d) same, (e) different compounds that are not isomers.

22.32 (a) stereoisomers: isomers that have the atoms connected in the same way but have different arrangements in three-dimensional space. (b) enantiomers: stereoisomers that are mirror images of one another. (c) diastereomers: sterreoisomers that are not enantiomers. (d) geometric isomers: cis-trans isomers, stereoisomers that results from restricted rotation. (e) trans-isomer: a geometric isomer in which two similar atoms or groups are on opposite sides of a double bond or ring. (f) cis-isomer: a geometric isomer in which two similar atoms or groups are on the same side of a double bond or ring.

22.34 (a) CH₃CH₂C^*(OH)CH₃, (b) achiral, (c) achiral,

22.42 (a) one: CH₃CH₂Cl, (b) two: ClCH₂CH₂Cl and CH₃CHCl₂, (c) two: ClCH₂CHCl₂ and CH₃CCCl₃, (d) two: Cl₂CHCHCl₂ and ClCH₂CCl₃, (e) one: Cl₂CHCCl₃, (f) one: Cl₃CCCl₃

22.44 (a) 4-methylheptane, (b) 2-methyloctane, (c) 3-methylheptane

22.46 (a) aromatic, (b) amide, (c) alkene, (d) ester, (e) ketone, (f) alkyne, (g) alkane, (h) amine

22.48 (a) 2-bromopentane, (b) 1-chloro-3-methylhexane, (c) 1-chloro2-methylpropane

22.52 (a) CH₃CH₂CH₂CH₂OH, (b) CH₃CH₂CH₂CH₂OCH₃, (c) CH₃CH₂CH₂CH₂SH, (d) CH₃CH₂CH₂CH₂N₃, (e) CH₃CH₂CH₂CH₂I

22.53 (a) (CH₃)₂CHCH₂CH₂I + Cl^-, (b) CH₃CH₂CH₂CH₂CH₂I + Cl^-, (c) CH₃CH₂CH₂CH₂OH + Br^-, (d) H₂C==CHCH₂SCH₃ + Cl^-, (e) CH₃CH₂CH₂OCH₂CH₃ + Cl^-

22.57 (a) CH₃CH₂CH₂Br + OH^-, (b) CH₃CH₂CH₂CH₂Br + ^-OCH₂CH₃, (c) CH₃CH₂CH₂CH₂CH₂Br + ^-SCH₂CH₃, (d) H₂C==CHCH₂Br + ^-OOCCH₃, (e) CH₃I + (CH₃)₃N:

22.65 (a) CH₃CH₂CH₂Br + SH^- ® CH₃CH₂CH₂SH + Br^-, (b) no reaction, I- is a weak base and cannot displace OH^-, a strong base, (c) no reaction, Br^- is a weaker base than CH3COO^-, (e) CH₃CH₂CH₂I + CN^- ® CH₃CH₂CH₂CN + I^-, (f) no reaction,

See the rest in your book.