Question

5) Provide a structure consistent with all of the data for the following compounds. Unless otherwise stated, the IR data is not all inclusive, i.e. you may propose a structure which would include peaks not specifically noted but your structure must account for the peaks which are listed or which are excluded. a) Compound Q (C6H100) decolorizes Br2/CC14. IR peaks at 3500 cm- and 1640 cm"! NO absorption between 1700 and 1800 cm? b) Compound K (C6H100) does not decolorize Br2/CC14. No IR absorption between 1700 and 1800 cm or between 3200 and 3600 cm. 6) Propose structures consistent with the following data: a) C4H100 'H NMR spectrum singlet, a 1.28 (9H) singlet, a 3.10(1H) IR Spectrum broad peak from 3200-3550 cm-1 b) C7H30 'H NMR spectrum singlet, 02.43(1H)* singlet, a 4.58(2H) multiplet 7.28(5H) IR Spectrum broad peak from 3200-3550 cm-1 * this is an O-H proton

Answer 1

Note: Degree of unsaturation for 84168: chHent2 for of saturated Hydrogen8 = 146 I ha6 12 ) GH14 - for a Polecularfortula Hydrogens = 104 Degree of unsaturation = 14-10 22 It andicates tolecure has two double bonds on one Ring, one double bond (on) Two cyclic Rings.

(5) (a) the probable structure is compound (e) " Brg (Reddish brown) i (colorless (& Hoo) 3500 chut due 1640 cal que to to oth c=6 stretching stretching.

(b) the probuble structure (k) is D o g Berg hot Decatustiser (6 Hoo) Carbony fonctional group absent. ano band at 3200-3600 fil Indicated functional group absent. aroe

(6) @). C424600 bused on IR, H NMR spectrum The probable structure is HiC- Ć -OH Ch go butyl alcohol HI NHR: It consists of two types of protons, which are labelled as a, bo Ctglas H₂ C-& -ond ay din cal (туре с proton Integration multiplicity (ntly I Chemicalshittes) (PPT) 9H singler 1028 PPT 14 broad singles 3.10 PPh. In broad peak! IA IR spectron due to hold broad peak at 3200-300 11/11 stretching.

( G Hgo: H NMP, IR based on Data the probable CH2-OH structure is oh benzyl alcohol IR Duter > broad peak at 3200-3550 coil due to stretching HINNR: It consists of 3 Types of which are labelled has a, b, c. clip-otib protons, type of integration multiplicity inti) | Chemicushitt(8) PPM proton qH Singlet 4.58 PPM raj Singlet 2.43 PPM 7.28 pp1 NE 56 Multiplet 12/12