Example Analysis: 0 PP 10 Chemical shift (8) 2004 Thomson-BrocksCole a. Calculat

Question

Example Analysis: 0 PP 10 Chemical shift (8) 2004 Thomson-BrocksCole a. Calculate: elements/deg unsatn 4 b. dentiy the IR absorptions (after providing the structure). 818, 18-10=8,812 = 4 expect stretching absorption at 1600 cm for the conjugated benzene C-Cs, a stretching absorption at 3300 cm1 for the-OH function a stretching absorption at 3050 cm-1 for C=C-H stretch, and -a stretching absorption at 2950 cm1 for the C-H c. Analyze NMR spectrum. Peak 1: Ös 7.2 aryl? Peak 2 & 45 deshielded area-1.75 2 Hs Peak 3 2.5 OH? Peak 4:a 2.3 deshielded area-25 2HS 4 Hs 1 H 10Hs multiplet, may be a doublet of doublets-each-sees 1 singlet-sees 0.-may be doublet (note top), Sees- "funny looking-peak (squashed, fireplug) singlet,"seeso. area-3 area-1 d. Provide an appropriate structure. e Label each proton-NMR peak, ie, a, b, c, d, etc, appropriately. t Identify the number of carbon-13 peaks: 6 peaks expected in the 13C NMR spectrum Hd Hd Ha Ha-C He Hd

Explanation / Answer

A. Calculate: elements deg of unsaturation 5--à12; no unsaturation

B. IR absorptions:

OH stretching absorption at 3000 cm-1

C-H stretching absorption at 2800 cm-1

C–H bend or scissoring from 1470-1450 cm-1

C. peak a: triplet at 0.9 ppm (two terminal CH3 groups)

peak b: multiplet at 1.5 ppm (two CH2 groups)

peak c: peak at 1.8 ppm (OH group)

peak d: peak at 3.3 ppm (CH attached to OH and two alkyl groups)

D. expected structure is pentan-3-ol

E. image is not uploading here terminal CH3 are a and nect to CH3, two CH2 groups are b, OH is c and OH attached carbon CH is d

F. Expected peaks in 13 C are three, at 10, 35, 76

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