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IR Correlation Table |
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C-H Alkanes (stretch) 3000-2850 s -CH3 (bend) 1450 & 1375 m -CH2 (bend) 1465 m Alkenes (stretch) 3100-3000 m (out-of-plane) 1000-650 s Aromatics (stretch) 3150-3050 s (out-of-plane) 900-690 s Alkyne (stretch) ~3300 s Aldehyde 2900-2700 w C=C Alkene 1680-1600 m-w Aromatic 1600 & 1475 m, w C≡C Alkyne 2250-2100 m-w C=O Carbonyl 1780-1680 s C-O ROH,ROR,ROOH,ROOR 1300-1000 s O-H Alcohol, carboxylic acid 3600-3200 m N-H (stretch) 3500-3100 m (bend) 1640-1550 m-s C-N Amines 1350-1000 m-s C-X Alkyl Halide 600-900 w |
HDI
1. Answer the questions below (2 each)- note these are all independent questions
Name:
(a) label the defined stereocenter as R or S isomer – show your work for credit!
(b) draw a conjugate acid-base pair
(c) translate the ring into its chair form (you do not need to flip it)
(d) draw the major product of monochlorination of the molecule below
(e) draw an aromatic hydrocarbon which is NOT benzene
(f) identify the functional groups present in the molecule
(g) draw a hydrocarbon structure which would exhibit a signal at 3300 cm-1 in its IR spectrum
(h) provide a structure which fits the following terms:
(i) β-keto ester (ii) 3° alcohol
(iii) enamine (iv) bulky base/base only reagent
(v) anti Newman projection (vi) reducing reagent
(vii) cuprate reagent (viii) allylic carbocation
(i) Name or draw the following organic molecules
(i) (ii) 2,3-diethyl-4-methylcyclohexanone
(iii) butyl methyl ether (iv)
(v) 3-chloroaniline (vi)
(j) draw a 6 carbon non-conjugated diene
(k) circle a sp3 atom and square a sp atom in the molecule below
(l) draw a molecule with formula C4H11N which exhibits hydrogen bonding with water but not itself
2. Fill in the boxes below with the correct reagent, reactant or product(s). Show the correct
stereochemistry for products which require it (36)
(a)
(b)
(c)
(d)
(e)
(f)
(g)
(h)
(i)
(j)
(k)
(l)
(m)
(n)
(o)
(p)
(q)
(r)
3. Use priority rules to label the alkenes below as either the E or Z conformer- show your work for credit!
(8)
(a) (b)
(c) draw the Diels-Alder product of the alkenes in (a) and (b) above (don’t worry about
stereochemistry in product)
4. A molecule has been identified and the structure is shown below. Also supplied is the IR and H NMR
spectrum. Use these spectra to confirm the identity of the molecule as directed (17)
(a) identify the bond represented by the labeled peaks in the IR, list
these bonds with the spectra’s label (ex. Peak 1 = C-C)
Bonds from IR:
(b) for the labels on the H NMR below provide: (1) calculated integration value, (2) splitting pattern
and (3) the structural piece the signal represents (ex. B: 3H, t is a CH3-CH2 piece)
(c) to further justify the identification, explain why the other proposed structure doesn’t fit either the
IR or the NMR spectra
Other proposed structure:
5. Draw an arrow-pushing mechanism to explain the following conversions. Show all intermediate
structures and watch your arrows and charges (17)
(a)
(b)
(c)
(d)
(e)
6. Design a synthesis to make the following molecule starting from the indicated starting material.
Show the intermediate structure after each alteration (5)
7. Fill in the boxes below with the correct reagent or product (6)
(a)
(b)
(c)
8. Provide the mechanism for the formation of the benzene derivative shown. Remember to include the
step(s) to form the electrophile (4)
Scrap Paper
