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Organic Chemistry Lab I Final Exam Review This exam has 38 multiple choice questions and two numeric

answer questions. Bring a ruler or straight-edge so you can use a nomograph. This exam stresses basic calculations and concepts rather than memorizing specific compounds or details of procedures. Lab 1: Recrystallization and melting points How does the second batch of crystals compare to the first batch of crystals in a recrystallization How does the melting point of a pure compound compare to that of an impure compound !hat happens to the melting point of a pure compound if it still contains residual sol"ent !hat is the purpose of using a mixed melting point #an you do problems $ - 3 on the lab write-up Lab Extraction How do you determine which is the upper or lower layer in a separatory funnel !hy is aqueous %a&H used to extract carboxylic acid compounds from organic sol"ents How would you reco"er the original carboxylic acid after the extraction is complete !hy is it more effecti"e to extract a compound multiple times with small portions of sol"ent rather than once with a large portion of sol"ent Lab !: "istillation #an you use the nomograph on page 3' (3) for old manual* +ee question , on the lab report. #an you use the phase diagram on page 3) (-$ for old manual* +ee question 3 on the lab report. #an you calculate "apor composition using .aoult/s 0aw and the solution composition (1emorize .aoult/s 0aw* +ee problem - on the lab report. !hen do you use a fractional distillation instead of a simple distillation !hat is a theoretical plate Lab #: $olec%lar $odeling #an you predict which conformers for substituted cyclohexanes are most stable Lab &: Identi'ying an %n(nown Carboxylic )cid #an you calculate the neutralization equi"alent and relate it to the 1! 1emorize this equation. 2oes the neutralization equation always equal the molecular weight Ha"e you memorized the three follow-up tests to sodium fusion $. !hat does a blac3 precipitate from 4b,5 indicate ,. !hat does a blue color from 6e+&-76e35 indicate 3. !hat does a white8 pale yellow or bright yellow precipitate from 9g%&3 indicate Lab * and +: ,as Chromatography and -LC #an you calculate the amount of components based on pea3 areas #an you determine which component is present by interpreting spi3ed samples !hich compound exits the :# first8 the lowest boiling or highest boiling #an you calculate the .f for a T0# !hat is the mobile phase and stationary phase for T0# and :# respecti"ely

Lab .: Resol%tion and /olarimetry !hat are racemers and mesomers and can you identify them #an you determine the absolute configuration of a chiral carbon (.8+* !hy did you ma3e a diasteroemeric salt in this experiment !hat 3inds of compounds rotate plane-polarized light #an you calculate the percent purity of a sample based on its optical purity 1emorize equation. #an you do question $ and , on the lab report !hy did you add ;,#&3 (potassium carbonate* to the dichloromethane layer after the extraction Lab 10: Identi'ying an %n(nown aldehyde or (etone Ha"e you memorized the three oxidation tests for aldehydes and 3etones $. !hat does a sil"er mirror with the Tollen/s test indicate ,. !hat does a blue7green color with chromic acid indicate 3. !hat does a bright yellow precipitate with the iodoform indicate o !hat are the organic products of each of these reactions Lab 1: 2pectroscopy Ha"e you memorized the coupling patterns for proton %1. resulting from ad<acent #Hn/s 6or example8 #H3-#H,-#H, =& =#H3 would yield in this order a triplet8 a multiplet8 a triplet8 and a singlet respecti"ely. #an you calculate the index of hydrogen deficiency Ha"e you memorized the ma<or absorptions for the functional groups in >. (%H,8 -&H8 .#&&H8 .#&&.8 .#&.8 .#&H8 .#-#%8 .-&-.*. %ote8 you do not need to 3now the exact "alues. ?ou should 3now that carbonyls absorb between $'@@ and $'-@ cm-$ and that %-H and &-H bonds ha"e broad absorptions in the 3,@@-3A@@ cm-$ region. The &-H bond in carboxylic acid is between ,B@@ and 3@@@. !hat 3ind of carbons ha"e resonances greater than $@@ ppm !here should aromatic8 al3ene8 allylic and al3ane hydrogens show a $H resonance !here should an aldehyde or carboxylic acid $H resonance appear !hat happens to an amine8 alcohol or carboxylic $H resonance in the presence of 2,&