UK CHE 230 - Exam 1 Review 1 (47 pages)

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Exam 1 Review 1



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Exam 1 Review 1

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Pages:
47
School:
University of Kentucky
Course:
Che 230 - Organic Chemistry I
Organic Chemistry I Documents
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Draw the resonance structure indicated by the arrows 1 2 O O 3 O O Label each atom with the correct hybridization 4 sp3 sp3 HO sp3 sp3 O sp3 sp3 5 sp3 N sp2 sp2 sp3 sp2 6 O sp sp sp2 sp3 7 Draw H2NCH2 in its second best resonance structure H H N CH2 H N H CH2 H N CH2 H 8 Draw the best Lewis structure for CH3CHO a neutral molecule O C H3C H 9 Draw the Lewis structure for CH3COOH a neutral molecule O C H3C OH 10 Draw the Lewis structure for N2H2 a neutral molecule HN NH 11 Draw in the electron flow arrows in on the left hand structure that lead to the resonance structure on the right O O 12 In the empty box draw the best resonance structure of the lefthand compound and draw one or more electron flow arrows on the preexisting structure that lead to the new structure O O 13 O O 14 Cl Cl Cl Cl Cl 1 Cl Cl Cl 4 3 2 Label each of the following as an ionic or covalently bonded compound a NaF ionic b BrCl covalent c NaOCHe ionic Calculate the formal charge of nitrogen in each of the following compounds FC 5 4 1 2 4 1 a N b N N FC 5 2 1 2 6 0 FC 5 0 1 2 8 1 Draw the Lewis structure H a CH3 OH2 H H b CH3NO2 C O H H H C N H O H O Draw all possible isomers of C2H4O O HO C H3C H C H O CH2 H2C CH2 Are each of the following pairs isomers or resonance structures a H3C CH3 H3C C H2 CH2 C H2 Neither different formulas b O O Isomers same formula but different arrangement of atoms Draw a resonance structure of each and identify which is the major contributor a O H b O NH2 H NH2 O O H3C C C H CH2 H3C C C H CH2 Draw all possible resonance structures of the compound below and it s resonance hybrid CH2 CH2 CH2 CH2 CH2 CH2 Predict the geometry around each indicated atom a H2 C H3C CH3 C H2 tetrahderal CH2 b H3C OH Trigonal planar Draw the three dimensional structure of the following a CH3OH H H C H O H b CH3 2NH H H H H C H N H H Convert each molecule into a skeletal structure a CH3 2CHCH2CH2CH CH3 2 H b H H H H H3C C C H H H CH H3C CH3 Convert into Lewis structures a CH3 3COH CH3 H3C O H CH3 b CH3COCH2Br H O H H Br H H What is the hybridizatio of th eindicated atom a sp3 sp2 sp2 b CO2H sp Which is the weakest of the indicated bonds b a c A is the weakest bond due to it being composed of a sp3 and sp2 hybridized orbital thus having the least amount of S character NH2 HO a b B is the weakest b c bond strength increases across a row in the periodic table and N is to the left of O Draw the products and label each part O O OCH3 OH A A O B H CH3 HO CA CB NaNH2 B CB Na NH3 CA Draw the products and determine if the reaction occurs O O F3C O CH2CH3 OH F3C pka 0 2 pka 16 O NaCl O OH reactants favored CH2CH3 O Products favored O pka 5 HO HCl pka 7 Which is the strongest base HBr HCl or HF HF b c it is the weakest acid Identify the most acidic hydrogen H H b c H a H C is the most acidic hydrogen b c it s bonded to an sp hybridized carbon H Draw the products of each reaction and label the starting materials as a Lewis acid and base Cl Cl Cl Cl B LB Cl Cl Cl LB Cl Cl LA Cl B B Cl Cl Cl LA O B O Cl 1 Complete the following acid base reaction H O O O OH 2 Complete the following acid base reaction Draw only the organic products KOH OH H OH O O H K O H 3 O O H H OH OH 4 Choose the strongest acid H Cl H Br H S H H Br Both Cl and Br are further right than S And Br is further down than Cl So most acidic 5 SH SH PH2 OH Both O and S are further right than P And S is further down than O So most acidic 6 Choose the weakest acid OH CH3 SH CH3 C is further left than O and S so weakest acid 7 The following compound has two stereoisomers One has a dipole of 0 D and the other has a dipole moment of 2 95 D Draw the structure of the stereoisomer with dipole moment of 2 95 D Cl Cl Cl H Cl Cl H Cl H H Cl H Cl Cl H Cl H H 8 Rank the three compounds from least acidic rank 1 to most OH 3 SiH3 2 CH3 1 We know Si is more acidic than C because it is below C in the same column Although Si and O can t be compared directly O is much more acidic 9 Rank the following compounds from most acidic rank 1 to least O H3C H2 C 2 O OH H3C Cl H2 C OH Br 3 O O H3C H2 C 1 OH OH H3C H2 C H2 C OH 4 Acidity is based on the electron withdrawing effect of the four different substituents O is the most electronegative furthest up and to the right and thus gives the most acidic compd And Cl is more electronegative than Br b c electronegativity increases up the column 10 Draw the electron flow arrows that lead from starting materials to products in this acid base reaction H H H N H H H H H 11 O O H O N N NH O 1 Draw an aldehyde O RCHO R H 2 Draw an ester O R R O RCOOR or RCO2R 3 Draw a sulfide S R R RSR 4 Draw 1 1 dimethylcyclohexane 5 Draw 2 2 4 trimethylhexane 6 Draw trans 1 3 dibromocyclobutane Br H Br H Br Br Br Br Br H Br H 7 Draw cis 1 chloro 3 isopropylcyclopentane Cl Cl Cl H H H 8 Draw sec butylcycloheptane H Cl 9 Draw 2 2 4 4 tetramethylhexane 10 Draw the structural formula of an alkane that has eight carbons and only primary hydrogens CH3 CH3 H3C CH3 CH3 CH3 Primary hydrogens are attached to carbons attached to only one other carbon 11 Draw the conformation favored by 1 2 dichloroethane at equilibrium in the liquid phase by following this procedure H H Cl H Cl H anit H Cl H H Cl H gauche The gauche conformer is favored in the liquid phase due to a polar effect …


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