Organic Chemistry: Reactions and Mechanisms, Exams of Organic Chemistry

Download Organic Chemistry: Reactions and Mechanisms and more Exams Organic Chemistry in PDF only on Docsity! Name: C CH3 H3C CH3 Cl CH3CH2OH 25 degrees C CH3 H3C CH3 OCH2CH3 C C H H CH2CH3 H HBr CH3OOCH3 CH2BrCH2CH2CH3 CH3CH2OH PCC CH3CHO 2. Circle the reaction in the each of the following pairs that would occur faster. Briefly justify your choice. (12%) Reaction Pair Justification Br NaCN CN I NaCN CN OR Br NaCN H2O CN Br NaCN diethyl ether CN OR OH OH CH3 CH3 CH3 CH3 H3PO4 H3PO4 CH3 CH3 CH3 CH3 OR docsity.com 3. The reactions of E-2-butene and Z-2-butene with bromine generate different products. One of the alkenes produces a single, achiral molecule and the other produces a racemic mixture of two product molecules on reaction with bromine. Show the intermediate(s) and product(s) formed in these two reactions. (10%) Starting Material Intermediate(s) Product(s) E-2-butene Z-2-butene 4. Order the structures below from least acidic to most acidic. Provide a brief explanation for the most and least acidic. (9%) CH3CH2CH3CHHC CH3CH2OH CH3COH O H3O + A B C D E Least Most 5. Griseofulvin is an antifungal agent used to treat ringworm. Identify all nucleophilic and electrophilic sites in the structure of griseofulvin below. You may use ‘N’ to label nucleophilic sites and ‘E’ to label electrophilic sites. (8%) O O OCH3O OCH3 H3CO Cl H3C 6. Rank the following nucleophiles from least to most nucleophilic in diethyl ether. (6%) H2O CH3CH2OH HO - CH3CO2 - CH3CH2O - A B C D E Least Most docsity.com