Organic Chem I HW Question Example Guides By Julia K on LuvoLearn Problems from OWL UMass Amherst Fall Semester 2015 Alkyne Synthesis Question Examples First you want to add NaNH2 NH3 to form an acetylide ion which acts as a strong nucleophile Then adding CH3CH2I2 for additional carbons followed by lindlar NH3 reagent which reduces alkynes to alkenes and gives you the trans addition Chapter 10 Below I outline synthetic scheme steps necessary to complete OWL problems in Chapter 10 reagents Two part problem involving Gilman Synthetic scheme outline Chapter 11 Structure Determination Identification of an Alkyl Halide JK Compound X C 8 H 17 Cl is a chiral product of the radical chlorination of 4 methylheptane X reacts in S N 2 fashion with NaI in acetone to form Z C 8 H 17 I When the reactant is the R enantiomer of X only the R enantiomer of Z is formed Draw a structural formula for X do not show stereochemistry I am not really sure what the significance of talking about chirality was if you don t have to show stereochemistry but for me anyway this problem was easier than it looked at first These are the steps 11 EOC Questions Ch 12 13 Spectroscopy not on exam This is super helpful for these questions imo http orgchem colorado edu Spectroscopy irtutor analyzeir html Chapter 17 17 EOC Questions Drawing the structure of 2 methyl 2 butanol Butanol tells us it s a 4 carbon chain and an alcohol Counting from the side that gives the lowest number both methyl and the oh will be on the 2nd carbon Therefore sheet aka right side 5th down on back page This is like 42 on the reaction aldehyde from a primary alcohol 44 DMP synthesizes an T o synthesize Ethylbenzene from 2 Phenylethanol adding POCl3 pyridine will yield an alkene in place of the oh group To cleave the oh group and yield an ethyl add H2 Pd catalyst Another question I had was to make phenylacetaldehyde PhCH 2 CHO and you add DMP because it will create an aldehyde from your primary alcohol step in the problem LiH4 H3O T wo steps are shown here but this is a combined To create the product with LiAlH4 H3O the C O is cleaved replaced by C OH by LiAlH4 which also removes the R group and then we add H3O to get the final product List of Rxns for Reference handed out in Fall 2015 Professor and on Moodle in Organic Chemistry I Non Majors with Professor Schnarr
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