1) Choose one molecule from the set and create an 8-step synthesis scheme using the chosen molecule as your starting material. You need to write the complete set of reagents and draw the product expected from each step. Reagents typically used together are considered one step, eg. 1) LAH 2) H.O should be considered as one step Your 8 steps must include at least one reaction from each of the chapters, aldehydes and ketones, carboxylic acid derivatives, alcohols. You can repeat a reaction only once therefore your scheme could have 2 oxidations maximum etc. More specifically, your scheme can include: a) oxidations b) reductions c) Grignard reactions d) acetal formation cleavage e) Wittig reactions ) reactions or synthesis of an acid chloride, ester, amide or anhydride g) a reaction with SOC or PBry h) any reaction to synthesize or react alcohols 1) Iminelenamine synthesis hydrolysis 1) novel reagents such as Gilman and modified reducing agents 8-step Synthetic Scheme 8-step Synthetic Scheme:

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Spectroscopy: 3) Choose one intermediate in the scheme and list 2 peaks you would expect to see in the IR spectrum. Be sure to indicate the functional group and the approximate wave numbers. IR Peak List: IR Peak List Functional Group Approx. wavenumber Intermediate for IR Also, choose another intermediate and indicate 4 sets of hydrogens and list the approximate chemical shifts and the splitting you would expect to observe for the hydrogens shown. Label your H set A-D. H Set Splitting Chemical Shift 1000 lo Intermediate for TH NMR analysis

– + Fit to page Page view 1) Choose one molecule from the set and create an 8-stop synthesis scheme using the chosen molecule as your starting material. You need to write the complete set of reagents and draw the product expected from each step. Reagents typically used together are considered one step, e.g. 1) LAH 2) H2O should be considered as one step. Your 8 steps must include at least one reaction from each of the chapters, aldehydes and ketones, carboxylic acid derivatives, alcohols. You can repeat a reaction only once therefore your scheme could have 2 oxidations maximum etc. LJ CO OO TO 0 I / / O More specifically, your scheme can include: a) oxidations b) reductions c) Grignard reactions d) acetal formation/cleavage e) Wittig reactions avage f) reactions or synthesis of an acid chloride, ester, amide or anhydride g) a reaction with SOCl or PBry h) any reaction to synthesize or react alcohols i) Iminelenamine synthesis/hydrolysis j) novel reagents such as Gilman and modified reducing agent reactions or synthesis of an acid chloride croiset alcohol

Mechanism: 2) Choose one of your steps and draw the complete curved arrow mechanism for the conversion. Be sure your curved arrows are clearly shown for the step you choose. Transformation for mechanism Mechanism

Spectroscopy: 3) Choose one Intermediate in the scheme and list 2 peaks you would expect to see in the IR spectrum. Be sure to indicate the functional group and the approximate wave numbers. IR Peak List: IR Peak List Functional Group Approx. wavenumber Intermediate for IR Also, choose another intermediate and indicate 4 sets of hydrogens and list the approximate chemical shifts and the splitting you would expect to observe for the hydrogens shown. Label your H set A-D. H Set Splitting Chemical Shift 1 Intermediate for H NMR analysis

1) Choose one molecule from the set and create an 8-step synthesis scheme using the chosen molecule as your starting material. You need to write the complete set of reagents and draw the product expected from each step. Reagents typically used together are considered one step, e.g. 1) LAH 2) H.O should be considered as one step Your 8 steps must include at least one reaction from each of the chapters, aldehydes and ketones, carboxylic acid derivatives, alcohols. You can repeat a reaction only once therefore your scheme could have 2 oxidations maximum etc. More specifically, your scheme can include: a) Oxidations b) reductions c) Grignard reactions d) acetal formation cleavage el Wittig reactions reactions or synthesis of an acid chloride, ester, amide or anhydride g) a reaction with SOC or PB h) any reaction to synthesize or react alcohol 1) Iminelenamine synthesis hydrolysis j) novel reagents such as Gilman and modified reducing agents 8-stop Synthetic Scheme: 8-step Synthetic Scheme

Mecha 2) Choose one of your steps and draw the complete curved arrow mechanism for the conversion. Be sure your curved arrows are clearly shown for the step you choose Mechas Spec SRODY 3) Choose one intermediate in the scheme and list 2 peaks you would expect to see in the IR spectrum Be sure to indicate the functional group and the approximate wave numbers IR Peak List: IR Peak List Functional Group Appro vember Intermediate Also, choose another intermediate and indicate 4 sets of hydrogens and list the approximate chemical shifts and the splitting you would expect to observe for the hydrogens shown. Label Your H et A-D H Ser Solinting Chemical Shirt Intermediate for “H NMR analysis

1) Choose one molecule from the set and create an 8-stop synthesis scheme using the chosen molecule as your starting material. You need to write the complete set of reagents and draw the product expected from each step. Reagents typically used together are considered one step, e.g. 1) LAH 2) H2O should be considered as one step. Your 8 steps must include at least one reaction from each of the chapters, aldehydes and ketones, carboxylic acid derivatives, alcohols. You can repeat a reaction only once therefore your scheme could have 2 oxidations maximum etc. More specifically, your scheme can include: a) oxidations b) reductions c) Grignard reactions d) acetal formation/cleavage e) Wittig reactions f) reactions or synthesis of an acid chloride, ester, amide or anhydride g) a reaction with SOCl2 or PBr h) any reaction to synthesize or react alcohols i) Imine/enamine synthesis/hydrolysis 1) novel reagents such as Gilman and modified reducing agents

3) Choose one Intermediate in the scheme and list 2 peaks you would expect to see in the IR spectrum. Be sure to indicate the functional group and the approximate wave numbers. IR Peak List: IR Peak List Functional Group Approx. wavenumber Intermediate for IR Also, choose another intermediate and indicate 4 sets of hydrogens and list the approximate chemical shifts and the splitting you would expect to observe for the hydrogens shown. Label your H set A-D. H Set Splitting Chemical Shift Intermediate for ‘H NMR analysis