CHM 2210 02 10 Examination 1 June 4 2014 INSTRUCTIONS Read carefully Carefully separate all sheets This examination has 2 pages of problems 1 double sided answer sheet a periodic table and 1 blank sheet for scratch work Read each question carefully For 4 bonus points correctly complete as requested on both sides of the answer sheet print your name sign your name give the portion of your FSU e mail address that appears before the this is the same as your BlackBoard login user name give your row letter and seat number and give your Recitation Section number Put your answers in the spaces provided on the answer sheet Only answers on the answer sheets will be graded All will be collected hand in your answers sheet separately from the rest There is a total of 150 points plus 4 bonus points Before the next lecture go over problems about which you were not confident on this examination sheet do not make changes or additions to your returned graded answer sheet Write on a separate sheet of paper what items you believe that you were not given sufficient credit and the reasons why you think so Attach it to your original answer sheet and give it to Dr Hilinski after a lecture or during an office hour preferably within 2 weeks after it is returned Be sure to make and keep a photocopy for your records REGRADE POLICY If you have a question about the number of points that you earned on your graded exam answer 1 2 3 4 5 6 12 points For each of the compounds given to the right provide a name a CH3 2CHCH2CH CH2CH2CH3 2 b For parts 2a 2f consider the molecule given in problem 1b a 2 points How many tertiary hydrogens are there b 2 points How many quaternary Cs are there c 4 points Give the molecular formula of this compound d 2 points How many primary alkyl groups exist as substituents e 2 points For the number of Cs that you gave in part c of this problem what is the maximum possible number of Hs f 2 points How many methylene groups are there 6 points Provide a structural formula for 1 3 5 triethyl 1 isopropylcycloheptane For this problem you must give a complete structural formula showing all atoms and all bonding valence electrons 24 points Consider the following NH CH3 NH2 CH2 toluene aniline a One of the 5 resonance structures Lewis structures that contribute to the resonance hybrid of the conjugate base of Note that if you incorrectly duplicate resonance structures you will lose credit for that resonance structure If you give more than 4 resonance structures points will be deducted toluene is represented above as one of the products in the given chemical equation Draw the additional 4 resonance structures Lewis structures that contribute to the resonance hybrid of the conjugate base of toluene For each of the four Lewis structures resonance structures that you give you must show all atoms all bonding valence electrons all unshared valence electrons and each nonzero formal charge structural considerations provide a clear concise explanation but in as much detail as possible why this equilibrium lies to the left NOTE that a correct answer to this part is not that the pKa of aniline is less than the pKa of toluene because this is merely a restatement of the fact that aniline is more acidic than toluene b Clearly give the numerical value in degrees for the HCH bond angle in the conjugate base of toluene c The equilibrium shown above lies to the left This of course means that aniline is more acidic than toluene Using 15 points Draw structural formulas for 5 and only 5 constitutional isomers that have one and only one five membered ring and the molecular formula C7H13Cl Yes each of the constitutional isomers that you give must be a substituted cyclopentane Your structural formulas must have no nonzero formal charges and the most typical arrangements of bonding and nonbonding valence electrons Note that if you give the same isomer more than once points will be deducted for that isomer If you give more than 5 constitutional isomers points will be deducted For this problem you must give complete structural formulas showing all atoms and bonding valence electrons Do not give condensed structural formulas or bond line formulas 10 points Using the molecular formula for the compound shown to the right in the chemical equation give the balanced chemical equation for the combustion of the compound shown to the right CHM 2210 02 10 Examination June 4 2014 Page 2 21 points Consider each of the following Does the equilibrium lie to the left or right Choose one give left or right CH3CH2OH CH3CH2NH2 HO S CH3CH2O O CH3CH2NH3 SH a b c d e f g 7 8 9 HCl HI Cl I CH3 3COH CHNa CH3 2CHOK HC CH3CO2H CH3CH2O H2C CH CH3 3COK CH3 2CHOH HC CH2 CH3CO2 CH3CH2OH H2C CNa NH3 NH2 NH3 NH2 a CH3 CH2 4CH3 or b CH3 3CCH2CH3 Choose one give the letter a CH3 CH2 4CH2OH or b CH3 CH2 3CH2OH Choose one give the letter 33 points i Which compound is more soluble in water ii Which compound releases less heat when it is burned iii Which compound has the lower boiling point iv A Lewis base can also be known as v Which one is the most basic a CH3 3CO b CH3CH2O or c CH3 2CHO Choose one give the letter vi Which compound is more oxidized a an electrophile b a nucleophile or c a spectator ion Choose one give the letter a CH3 CH2 3CH3 or b CH3 2CHCH CH3 2 Choose one give the letter a CH3CO2H or b BrCH2CH2Br Choose one give the letter If they are the same give both letters a C5H9 b C5H11 c C5H12 or d C5H13 Choose one give the letter vii Which one is the molecular formula of a neopentyl group viii Which compound is less polar a CO2 or b CO Choose one give the letter ix Which compound is an alcohol that is not miscible with water Choose one give the letter a CH3CH2OCH3 b CH3CH2CH2OH c CH3CH2CH2CH2OH x Which one is a primary alkyl group xi Which compound is thermodynamically most stable a 1 1 dimethylpropyl b 1 2 dimethylpropyl c 2 2 dimethylpropyl Choose one give the letter a octane b 2 methylheptane c 2 2 dimethylhexane Choose one give the letter b Using Lewis structures for each reactant and each product and using curved arrows appropriately a Using Lewis structures for each reactant and each product and using curved arrows appropriately to 15 points Consider the structural formula of acetaldehyde given to the right show the flow of electrons in the reactants give a chemical equation for the reaction between hydroxide ion HO and acetaldehyde in which hydroxide ion acts as a Lewis base and acetaldehyde acts as a Lewis acid IMPORTANT For this part