110 Write a condensed structure for the following Lewis structures. Η Η Η Η Η Η Η Η Η Η Η Η |||||||||II H=C=C=C=C=C=C=C=C=C=C=C=C-H |||||||IIIII Η Η Η Η Η Η Η Η Η Η Η Η d. b. Ο Η Η Η Η Η Η Η Η Η ΤΤΤΤΙΤΤΤΤ H=C=C=C=C=C=C=C=C=C=C=C=C-H H CIH H-C-H H Τ.. Η Η Η Η | H-C-H Η Η H-C-H | Η Η H=C=H …..... Η Η Η Η Η Η Η | H-C-H Η Η Η III H=C=C=C=C=C=C=C-C-H ΤΤΤΤ... Η Η Η Η Η Η Η Η Η 1 Η Η Τ. 196

un muinsup to 2192 griwellol and to riass of brot 91 fals 9. For the following skeletal structures, add the appropriate bonds and nonbonding electrons so each atom will have zero formal charge and a filled octet with the exception of hydrogen. H—C—C—C—C-H12-ais H H H—C—C-C-C-H | | | H H H H H y H C-CH F C woll (d W 2 on sa (d

Write in any formal charges not equal to zero. If there are none, please check the box below. :0 A H-C-C-H | | H H ☐ There are no missing formal charges. !

Order the following carbon-carbon bonds in order of increasing vibrational frequency (lowest to highest in cm-1) I C=C 0 0 0 0 | < ||| < || || < ||| < | || < | < ||| ||| < || < | II C-C III C=C

Convert the following line-bond structures into molecular formulas: (a) CH₂OH H H H H کی C= = с с C )-1 H (c) H、 N. с (=^ 0=C с FO Aspirin (acetylsalicylic acid) 0 )=0 с C C=0 OH H C || H CH3 ć с N Nicotine C 1 с с H HY C-C T H H CH3 )—I C H I I H (b) (d) HO H 4-C I HO HO H H₂ H-C C=0 Vitamin C (ascorbic acid) C=C CH₂OH C-O C C-C HO но| | H H OH OH Glucose H OH 11

PROVISIONAL LEWIS STRUCTURES T01/S02 For each provisional structure, enter the central atom formal charge (if not zero, enter the sign before the value) and, separating by comma without any space, indicate (Y or N) if it is the correct Lewis structure. For example, your answer could be "-2,Y". :ä: H - C -H | CH2CI2 BrF2+ :o: H-ö-B Н — Ве— н :o: B(OH)4 BeH2

||| = O PRINCIPLES OF ORGANIC CHEMISTRY Identifying rigid parts of an acyclic organic molecule In the actual molecule of which this is a Lewis structure, which of the labeled distances can change? H marked O G: F H B C H A N. unmarked G с N O H 0,0.... List all the distances that can change. For example, suppose all the distances were measured at a certain time, and again 0.1s later. If distance A might be 50% bigger or smaller the second time, but all the other distances are certain to be the same, you should write "A". If A and B might be different the second time, but no other distances, you would write "A, B". And so on. Note for advanced students: you can assume the molecule is dissolved in an appropriate solvent at room temperature. X 0/5 You can click the "unmarked" tab to see the molecule without any of the distances marked. S Jacari V 18 CO olo Ar

MOLECULES Drawing a skeletal structure from a Lewis structure Convert the Lewis structure below into a skeletal structure. H H-C-H H :0: || -N-C=ċ-c-0-C-H H Н-С—С- H H Н—С—Н Н H

Determine the formal charge on the nitrogen atom in each of the structures. NH3 NH2 ート N. H. H. H2N-OH C F G All nonbonding electrons are shown. What is the formal charge on the nitrogen atom in What is the formal charge on the nitrogen atom in structure A? structure B? 00 00 :O: :0=z :O:

The bond dissociation energy to break 9 C-H bond(s) in 1 mole of hexane (CH₃CH₂CH₂CH₂CH₂CH₃) molecules is