A compound with the molecular formula C_2H_2O shows a proton NMR spectrum with c

Question

A compound with the molecular formula C_2H_2O shows a proton NMR spectrum with chemical shifts at the following 5 values: 7.2 ppm (S H's) 23 ppm (2H's) 3 ppm (1 H) Suggest a structural formula for C_2H_2O which is consistent with these data. Match each substance in the left column with its description in the right column. Aromatic compound Adds water to an alkene BH_2 THF Catalyzes reduction of alkynes to alkenes Na_2Cr_2O_2/H_2So_4 conjugated double bonds in a ring with 4N + 2 pi electrons Electrophile Converts alkyl halide to a Grignard reagent LIAIH_4 Converts-OH of an alcohol into a good leaving group Lindlar's catalyst (Pd/Baso_4, quinoline) Negative charge mg Oxidizes aldehydes PCC (pyridinlum chlorochromate) Positive charge Tosylate group .Reducing agent

Explanation / Answer

8. Formula = C7H8O

degree of unsaturation = 4

1H NMR

7.2 ppm (multiplet, 5H) for Phenyl protons

2.3 ppm (singlet, 2H) for benzylic CH2

3.0 ppm (singlet, 1H) for OH proton

Possible structure,

C6H5-CH2-OH

9.

Aromatic compound : C. conjugated doublet bond with 4n + 2 pi electrons

BH3,THF : A. Adds water to an alkene

Na2Cr2O7,H2SO4 : H. Oxidizes aldehydes

Electrophile : I. positive charge

LiAlH4 : J. Reducing agent

Lindlar's catayst : B. catalyzed reduction of alkynes to alkenes

Mg : D. converts alkyl halide to grignard reagent

Nucleophile : F. negative charge

PCC : G. Oxidizes first degree alcohol to aldehydes

Tosylate group : E. converts OH to a good leaving group

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