CHM 2210 01 06 Examination 1A June 5 2013 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 2 bonus points correctly complete as requested on both sides of the answer sheet print your name sign your name and give the portion of your FSU e mail address that appears before the or give the last 4 digits of your FSUSN Put your answers in the spaces provided on the answer sheet Only the answer sheets will be collected only answers on the answer sheets will be graded There is a total of 140 points plus 2 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 12 points For each of the compounds given to the right provide a name For parts 2a 2f consider the molecule given in problem 1a a 2 points How many secondary 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 tertiary alkyl groups exist as substituents e 2 points For the number of Cs in this molecule what is the maximum possible number of Hs f 2 points How many secondary Cs are there 8 points Provide a structural formula for 2 sec butyl 4 4 4 dimethylpentyl 1 isobutylcyclooctane For this problem you must give a complete structural formula showing all atoms and all bonding valence electrons a Using Lewis structures for reactants and products and using curved arrows to 25 points Consider propene and acetaldehyde Recall that for a Lewis structure you must show all atoms all bonding valence electrons all nonbonding valence electrons and all nonzero formal charges show the flow of electrons in propene give the chemical equation that shows the heterolytic dissociation of one of three CH bonds in the methyl group of propene to give H and the corresponding conjugate base If resonance structures exist for the conjugate base give all important resonance structures that contribute to the resonance hybrid for the conjugate base Clearly indicate the value of each of the HCH bond angles in this conjugate base of propene acetaldehyde give the chemical equation that shows the heterolytic dissociation of one of three CH bonds in the methyl group of acetaldehyde to give H and the corresponding conjugate base If resonance structures exist for the conjugate base give all important resonance structures that contribute to the resonance hybrid for the conjugate base Clearly indicate the value of each of the HCH bond angles in this conjugate base of acetaldehyde more acidic one Provide a clear concise explanation why one is more acidic than the other c Using structural considerations identify which of the two Hs the one in propene or the one in acetaldehyde is the b Using Lewis structures for reactants and products and using curved arrows to show the flow of electrons in 15 points Draw structural formulas for 5 and only 5 constitutional isomers that have one and only one four membered ring and the molecular formula C7H14 Yes each of the constitutional isomers that you give must be a substituted cyclobutane 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 2 3 4 5 6 CHM 2210 01 06 Examination 1A June 5 2013 Page 2 7 18 points Consider each of the following Does the equilibrium lie to the left or right Choose one give left or right a CH3CH2CO2H CH3CH2NH2 CH3CH2CO2 CH3CH2NH3 b SH ONa SNa OH c I HCl HI Cl d CH3 2CHO HF CH3 2CHOH F e HC CNa CH3CH3 HC CH CH3CH2Na f HO O O OH 8 9 a CH3 CH2 3CH3 or b CH3 3CCH2CH3 Choose one give the letter a CH3 CH2 4CH2OH or b CH3 2CHCH2OH Choose one give the letter 24 points i Which compound is less soluble in water ii Which compound releases less heat when it is burned iii Which compound has the lower boiling point iv A Lewis acid can also be known as v Which one has the lowest pKa a CH3 3COH b CH3CH2OH or c CH3 2CHOH Choose one give the letter vi Which compound is more reduced a CH3 2CH CH2 2CH3 or b CH3 2CHCH CH3 2 Choose one give the letter a an electrophile b a nucleophile or c dienophile Choose one give the letter a HOCH2CH2CH3 or b H2C C CH2 Choose one give the letter If they are the same give both letters vii Which one is the molecular formula of a phenyl group viii Which compound is less polar a BF3 or b NH3 Choose one give the letter a C6H6 b C6H5 c C6H12 or d C6H11 Choose one give the letter a Using Lewis structures for each reactant and each product and using curved arrows appropriately 14 points Consider the structural formula of cation A given to the right to show the flow of electrons in the reactants give a chemical equation for the reaction between water H2O and cation A in which water acts as a Lewis base and cation A acts as a Lewis acid IMPORTANT For this part a of problem 9 the Lewis base that you give cannot also be a Br nsted Lowry base the Lewis acid that you give cannot also be a Br nsted Lowry acid b Using Lewis structures for each reactant and each product and using curved arrows appropriately to show the flow of electrons in the reactants give a chemical equation for the reaction between water H2O and cation A in which water acts as a Br nsted Lowry base and cation A acts as a Br nsted Lowry acid Do not give the same answer that you gave in part a of this problem Recall that for a