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UT CH 301 - Practice Problem Chapter 3 & 4

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Practice Problem Chapter-3 & 4-Donot Turn In | Dr. Shagufta Shabbir 1 Q1-Determine the stereocenter of the following molecules. If there is no chiral center then select option write Achiral. HCH3ClHCClCHCH3BrHCH3OHOHOH CH3H3COHHOHOBrH3CCH3CH3CHCHOHOCOOHH NH2CHOCOOHH2NOHHCOOHHO CH3HCH3H3CCH3H HBrCH2CH3HBrHOH2C CH2SHHHCH3Practice Problem Chapter-3 & 4-Donot Turn In | Dr. Shagufta Shabbir 2 Q2-For each of the molecules drawn below state their stereochemical relationship to each other. Whether they are constitutional isomers, configurational isomers, or conformational isomers. Assume no bond rotation for all the molecule drawn. S.N Molecules Relationship 1 2 3 4 5 6 7 8 9 10 11 12 OHOOOHCH3CH2H3CCH3CH2H3CH3CHCH3HClBrH3CBrCH3HClHH3C CH3H3CCH3ClClBrFBrFHH3C CH3HCH3H3CCH3H3CHCH3HH3CCH3H HH3CHHOCH3HCH3HOHH3C CH3HOHHOPractice Problem Chapter-3 & 4-Donot Turn In | Dr. Shagufta Shabbir 3 Q3-For each of the pair of molecules drawn below state their relationship to each other. Whether they are diastereomers, enantiomers or different ways of drawing the same molecules. Circle the meso compounds. For chair conformation you can convert them into planar form to determine if they are the same molecule or enantiomers or diastereomers. For chair conformation you can convert them into planar form to determine if they are the same molecule or mirror images or not mirror images of each other. S.N Molecules Relationship 1 2 3 4 5 6 7 8 H3CCH3HHHOOHH3CHOCH3HHOHCH3CH2H3CCH3CH2H3CCH3H3CH3CCH3H3CHCH3HClBrH3CBrHHClCH3H3C CH3H3CCH3OHHClHBr FClHOHBrF HHH3C CH3HCH3HOHH3COHHCH3H3CBrFBrFPractice Problem Chapter-3 & 4-Donot Turn In | Dr. Shagufta Shabbir 4 9 10 11 12 Q4- The following compounds is guanidine it has two sites that can accept protons. Circle the stable cation that predominate in solution A or B. Q5- Rank the following in order of their increasing acidity. (1 =least acidic, 4 = most acidic) Q6- Rank the following in order of their increasing Acidity. (1= least acidic, 4 = most acidic) HH3C CH3HCH3H3CCH3H3CHCH3HH3CCH3H HH3CH3CCNHNH2ClAClH3CCNHNHHH3CCNNH2HORHHHBCH2OHOH3CCH2OHOH2CClHCOHOH3CCOHOClClH3CClOHNH2OHOSHPractice Problem Chapter-3 & 4-Donot Turn In | Dr. Shagufta Shabbir 5 Q7-a)- Convert the line structure of the following amino acid into a Fisher Projection. Label the chiral center on the line structure R or S and label the Fisher Projection D or L. Q7-b)- Convert the line structure of the following amino acid into a Fisher Projection. HSCNCysteineR or S?Fisher ProjectionD or L?H HHOOCNIsoleucineFisher ProjectionOOH HHPractice Problem Chapter-3 & 4-Donot Turn In | Dr. Shagufta Shabbir 6 Q8- For each of the molecule circle the most acidic hydrogen? Circle only one type of hydrogen. If the molecule has two or more equivalent hydrogen’s or the same type of hydrogen’s draw a circle around all the equivalent hydrogen’s. CCCHCHHCCOONHHHHHHCCCOCHHOCCOCHHCCHHCHOOHHNHHHHHCCOOCHHHHHOHCCOHCHH HHSHOHCOHHHHHHOCHHHHHHHHPractice Problem Chapter-3 & 4-Donot Turn In | Dr. Shagufta Shabbir 7 Q9a) Calculate the Keq for the following reaction from the pKa given. Circle the side of the reaction that predominates at equilibrium. Keq = Q9b) Draw the reaction coordinate diagram of the above reaction. Label the reactants, products, transition state and the activation energy on the diagram. NH2NHpKa ~30pKa ~ 10OOHEnergyReaction CoordinatePractice Problem Chapter-3 & 4-Donot Turn In | Dr. Shagufta Shabbir 8 Q10-Circle the side of the equation that predominates at equilibrium. Then in the box write the predominate reason why that side predominates. Choose the reason from the following options. You may choose multiple valid options for your reasoning. A. Electronegativity of the atom B. Size of the atom C. Hybridization D. Inductive Effects E. Resonance


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