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  CHM 234: Worksheet #1  Fall 2011 Due: Tuesday, August 30 th  in cass  Dr. Halligan  A! ine Ange$keeta $tructures One of the most important things to become comfortable with right away in OrganicChemistry is line angle structures (also called s!eletal structures #. $n a line anglestructure% the carbons and hydrogens are not drawn in. $t is assumed that each carbonhas a sufficient number of hydrogens so that it has a total of & bonds. 'ince hydrogenonly has 1 alence electron% it can only hae one bond. )lways include lone pair electrons for the heteroatoms (i.e. *% O% halogens% etc.#. +his will be ery importantfor writing reaction mechanisms. ,eometry is important when you draw line anglestructures so ta!e note of that in the e-amples proided. %&a'(es: a.Here are seeral ways to represent 2)Methy(entane . +he structure on the left is the line angle (s!eletal# structure. +hey are a lot uic!er to draw and easier to wor! with for this course. CCCCCCHHHHHHHHHHHHHHC 6 H 14 2-Methylpentane CH 3 CH 2 CH 2 CH(CH 3 ) 2  b.Here are some e-amples of structures that include heteroatoms. Do you recogni/e some of these functional groups (i.e. !etone% amide% alcohol% al!ene% al!yne% ether% ester% amine% nitrile% aromatic ring% etc.# oo! in chapter  for assistance. NH 2 OH 2 CH 2 CCH 2 CHH 2 CCNH 2 OOHCCCCCHHHHHHHHHOHOOCCCCCCCOOCCHHHHHHHHHHHHHHC 5 H 10 OC 9 H 14 O 2 C 6 H 11 NO 1.2.3.  *ro+e's: 1.Determine the molecular formula for the following structures ( a)  #. 3rite in the missing lone pairs of electrons.  -!Degree o .nsaturation 3hen determining a possible structure for a molecular formula% it is helpful to calculate the total number of rings 4 pi bonds ( Degree o .nsaturation # that the structure will hae. %&a'(e: 5roide  possible s!eletal structures for C / H 10  . irst  calculate the Degree of 6nsaturation7 U =2C + 2 - (H + X) + N2U  = Degree of Unsaturation (total numer of rings !lus !i on s) C  = numer of #arons H  = numer of $% rogens X  = numer of $alogens (&' Cl' r' ) N  = numer of nitrogens Note:  *$e numer of o+%gen atoms oes not a!!ear in t$is e,uation- U =2C + 2 - (H + X) + N22(7) + 2 - (10 + 0) + 02 = U = 14 + 2 - (10 ) + 02 = 16 - 10262 == 3 Note:  (e #areful .it$ t$e or er of o!erations in t$is e,uation- /an% !eo!le get t$e .rong ans.er- $econd,  draw a structure that has 8 carbons and a degree of unsaturation of  (total number of rings and pi bonds#. $nclude the o-ygen atom in this structure% !eeping in mind that o-ygen gets two bonds. $f you do this% you will automatically hae the right number of hydrogen atoms. OHOO C 7 H 10 OC 7 H 10 OC 7 H 10 O  *ro+e's: 2.Calculate the Degree of 6nsaturation then proide two possible s!eletal structures for each molecular formula. Draw in lone pairs of electrons where appropriate.a.C & H 9  * b. C : H 10 O 2 c. C  H 8  *Od. C ; H 10 Cl 2 e. C 11 H 11  *O

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Jul 23, 2017
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