1-26 continued H H-0:H :0: H (c)H-C=O c-c-2-H (d)H H HHHH H H H 1-27 In each set below.the sccond structure is a more correct line formula.Since chemists are stand for C-0-0-H.Likewise for CHO. (a) (b) N三C CHO OH OR ORN三C (c) COOH OH OH CHO OH 1-28 H H these are the only two possibilities. a) H一 H and H HH H H help you visualize these structures HH b) these are the only two possibilities, H-C- -H help you visualize these structures
1-26 continued (c) .. H-O: H :0: I I II H-C=C-C-C-C-O-H I I I I •• H H H H 1-27 In each set below, the second structure is a more correct line formula. Since chemists are human (surprise!), they will take shortcuts where possible; the first structure in each pair uses a common abbreviation, either COOH or CHO. Make sure you understand that COOH does not stand for C-O-O-H. Likewise for CHO. (a) /'... � /' � � ..... COOH OR (c) �COOH OH OR�OH OH 0 1-28 H H H H OH o (b) N C�CHO o OR N - CTIYH o 0 CHO OR H H H H (a) 1 I 1 1 H-C-C-C-C-H I I 1 I H H H H 1 1 I and H-C-C-C-H I 1 1 H C H /1' these are the only two possibilities, but your structures may appear different-making models will help you visualize these structures (b) H H H I I 1 H-C-C - N: I I I H H H H H H H H H I I I and H - C -N- C - H I I H H 14 these are the only two possibilities, but your structures may appear different-making models will help you visualize these structures
1-28 continued HH H 6- -c-: 0- -C-H C-C-H HHHHH H HH H HH:O:H 0 -c-H H-c=c-6-H H-c These are the only three (d)H- -H structures with this molecular HH formula 1-29 HHH H (a)oy three 0-9 -C-H H- -0-C-H H-c- C-H structures H OH HOCH2CH2CH3 CH3CH2OCH3 CH3CH(OHCH3 (b)There are several other possibilities as well. H H-C- c-c-H H- c-C-H H-c=c-C-0-H H-C=c- HH H HH H OH CH3CH2CHO CH;COCH H2C=CHCH2OH H HC=C(OH)CH3 H-C=C-0-C-H HHH H2C CHOCH3 es not nave enougn atoms to bo one carbon: HH H two carbons:H-CC-H H-C=C-H H-C-C-H H-C-H C2H2 C.Ha HH C2Ho HH HCHa H HHH three carbons:H-CEC-C-H H-C=C-C-H H-C-C-C-H C;H CH C3Hs HH 15
1-28 continued (c) There are several other possibilities as wel l. Your answer may be correct even if it does not appear here. Check with others in your study group. H H H H H H I I I I I I :O -C-C-C - O: :O - C-C-O- C-H I I I I I I I I I HHH HH HHH H H :0: I II (d) H-C-C-H I H 1-29 H-C= C-O-H I I H H H H H I I I :0: / \ H-C-C-H I I H H H H H I I I (a) only three possible structures O-C-C-C-H H-C-C-O-C-H I I I I H H H H HOCH2CH2CH3 (b) There are several other possibilities as well. H H 0 H 0 H I I I H H H CH3CH20CH3 H H H H I I I :O-C-C -C-H I I I I H H :0: H I H These are the only three structures with this molecular formula. H H H I I I H-C-C-C-H I I I H 0 H I H CH3CH(OH)CH3 H I I II H - C-C-C- H I II I H-C-C-C-H I H - C=C-C - O-H I H-C=C-C-H I I H H CH3CH2CHO H I H-C=C-O-C -H I I I H H H H2C= CHOCH3 I I H H CH3COCH3 I I I H H H H2C = CHCH20H I I I H 0 H I H H2C = C(OH)CH3 1-30 General rule: molecular formulas of stable hydrocarbons must have an even number of hydrogens. The formula CH2 does not have enough atoms to bond with the four orbitals of carbon. one carbon: H I H-C- H I H CH4 two carbons: H - C C -H H I three carbons: H -C C - C - H I H-C=C-H I I C2H4 H H H I H-C=C-C -H I I I C3H4 H C3H6 H H H 15 H H I I H-C-C -H I I C2H6 H H H H H I I I H-C - C-C-H I I I C3HS H H H
1-31 H H H (b)H_ H (c) H H H HHH O: (d)H-N_ -C-0-H (e) H H-C -H H 6 (g) o: (h) 0 O-H H -C-H H 1-32 (a)CsHsN (b)CaHgN (c)CaHoNO (d)CaHgNO2 (e)CuH2INO (0CgH180 (g)CHgOS (h)CoHeO3 1-33 (a)100%-62.0%C-10.4%H=27.6%oxygen 品mcre6eucs-MaNY 5.7+1. =103aeH÷1o=595-6H 1.3 mokes 1.mles1 H HHH H O H-C-C-C-C-C-C-0-H (b)empirical formula =CHo →empirical weight=58 HHHHH molecular weight 117,about double the empirical weight HH HH H O H-0-C-C-c-C-C-C-H double the empirical formula molecular formula HH HHH CH1202 H-C- -C-C-C-O-C-H HH HHH 16
H H (b) H ..... � _ �_H H I \ H ..... C C .... / ,0 0/ " H N H I H H H H :0: I I I " � H - N - C-C-C-C-O -H I I I I H H H H (g) H H \ I C-C :0: H , II \\ " (e) H - C-C C-S==O 1-32 (a) CsHsN (f) C9H1 SO (b) C4H9N (g) C7Hs03S / \ / I H C= C :0: I \ I H H H (c) C4H9NO (h) C6H603 H H \ I /C, ,....H :N C, H II H I H \ /C, I H H-C C-H H H \ I I I,.... H H-C-C C H I 1 "00 / / (h) O-C-C-H H H \" :0: ·0· II H 0 , , 0 C_H H I \ H H H , /C, I /C,oo C C O-H \\ I C-C-H / H I H 1-33 (a) 100% - 62.0% C - 1 0.4% H = 27.6% oxygen (c) some possible structures-MANY other structures possible: 62.0 g C _ . _ _ 12.0 g/mole - 5. l7 moles C -;- l.73 moles - 2.99 - 3 C 10.4 g H = 10.3 moles H -;- l.73 moles = 5.95 == 6 H l.01 g/mole 1��06 g7�ole = l.73 moles ° -;- l.73 moles = 1 ° (b) empirical formula = I C3H60 I c:::::> empirical weight = 58 molecular weight = 1 17, about double the empirical weight q double the empirical formula = molecular formula = C6H1 202 I 16 H H H " H , "C, ' H-C C-O-H I I H-C C-O-H " 'c" , H '" H H H H H H H H ° I I I I I II H-C-C-C-C-C-C-O-H I I I I I H H H H H H H H H H 0 I 1 I I I II H-O-C-C-C-C-C - C-H I I I I 1 H H H H H H H H H 0 H I I I I II I H-C-C-C-C-C-O-C-H I I I I I H H H H H
1-34 Non-zero formal charges are shown by the atoms a)H-C=N=N:→H-C二N≡N: HH H (b) Hc-N-的 H H H (H-c=c-c-H (d)H-c = (e)H-C- -H HHH H0: H C H H HH 1-35 The symbols""and""indicate bond polarity by showing partial charge.Electronegativity a8-808-8-8 large small large small large 88* 88 8*8 (j)C-Br large large large large small 治nsmcacmsmhareabmsinicairdposioasfayaommorsosioasa -only the position of electrons is different (c)resonance forms-only the position of electrons is different (d)resonance forms-only the position of electrons is different (e)different compounds-a hydrogen atom has changed position (f)resonance forms-only the position of electrons is different (g)resonance forms-only the position of electrons is different (h)different compounds-a hydrogen atom has changed position (i)resonance forms-only the position of electrons is different (j)resonance forms-only the position of electrons is different 1-37 (a) H0 H:0: H-C- -二H→H-C-C=c-H H H H H (b)0: =C- C-H→H-C -C=C-H+H-C=C C三C一H HHH HH H HHH 17
1-34 Non-zero formal charges are shown by the atoms. + • • - + (a) H-C=N=N: .... .. I----I .. � H-C- N -N: 1 1 H H H + 1 + H H I 1 (b) H H H , 1/ H C , + 1 •• H - C-N-O: / I H C (c) H - C=C-C -H (d) H - C-N=O (e) H-C-O-C -H I +1 1 H /1' H H 1 1 1 H H H 1 1 H :0: .. - H C H / 1 ' H H H 1-35 The symbols "8+" and "8-" indicate bond polarity by showing partial charge. Electronegativity differences greater than or equal to 0.5 are considered large. 8+ 8- 8- 8+ 8- 8+ 8+ 8- 8+ 8- (a) C-CI (b) C-H (c) C-Li (d) C-N (e) C-O large small large small large 8- 8+ 8- 8+ 8- 8+ 8- 8+ 8+ 8- (f) C-B (g) C-Mg (h) N-H (i) O-H (j) C-Br large large large large small 1-36 Resonance forms must have atoms in identical positions. If any atom moves position, it is a different structure. (a) different compounds-a hydrogen atom has changed position (b) resonance forms-only the position of electrons is different (c) resonance forms-only the position of electrons is different (d) resonance forms-only the position of electrons is different (e) different compounds-a hydrogen atom has changed position (f) resonance forms-only the position of electrons is different (g) resonance forms-only the position of electrons is different (h) different compounds-a hydrogen atom has changed position (i) resonance forms-only the position of electrons is different (j) resonance forms-only the position of electrons is different 1-37 (a) H :0: I II H-C-C-C-H (b) :0: I 1 H H .. .. .. H :0: i I H-C-C=C -H :0: I 1 H H :0: II H-C -C=C-C -H II I I I I H H H ..... .. I----J .. � H-C-C-C=C-H ..... .. f----J .. � H - C=C-C =C-H I 1 I 1 1 I H H H H H H 17
1-37 continued CH =0 N-H 0 CH-c=c- -c=c-c-cH→CH- HH HHH HHHH CH3-C-C=C-C=C-CH OnRapra6cisheeer6Tedtnc0地eocneiRetor le or triple bond,or next to a non 18
1-37 continued (c) (d) + < > CH2 4 • OCH,- + ( ) CH, 0- 0/ � /; CH2 ... � CH2 0+ + + ... 0----0 + � � .. (e) < > �: 4 • 00 ---- -:0=0 . - . . . /- (f) < > �: -o� + + ( >-H 4 • CN-H - CN+ -H + (g) 0 0 .. • +0 .. ---- 0 � o 0+ .. . . (h) Q _ Q . �_ Q (i) :0 : :0 : :0 : .. - + CH3 -C=C-C= C-C-CH3 ----- + CH3-C=C-C-C=C-CH I I I I I 3 I I I I I H H H H H + / H H H H H CH3 - C - C = C - C = C -CH3 I I I I I H H H H H (j) no resonance fonns-the charge must be on an atom next to a double or triple bond, or next to a nonbonded pair of electrons, in order for resonance to delocalize the charge 18