1.

The mass spectrum an benzylhalide (haloalkyl bezene) is given:

CHAPTER 12&13- (MS, IR, NMR -Practice Exercises) CHEM 2425 Dr Pa!"a#a$ % Dr C!eri& % Dr Desse$s

a) Identify the parent peak

b) Identify the base peak

c) Determine the possible structure for the compound d) hat is the molecular structure for the most stable cation fragment (most intense peak) !. "ive several types of spectroscopic data IR, 1H NMR# and MS of particular compounds. hat are they$ a) C5H10O

b) C8H7N

c) C7H14O

% . &ach of the follo'ing compounds is characterized by a single 1( )*+ spectrum that consists of only a single peak having the chemical shift. Identify each compound. a) C8H18 , - ../ ppm b) C4H9Br , - 1.0 ppm 1. &ach of the follo'ing compounds is characterized by a single 1( )*+ spectrum that consists of t'o peaks# both singlets# having the chemical shifts indicated. Identify each compound. a) C6H8 , - !.2 ppm (1() and 3.4 ppm (1() b) C6H10O2, - !.! ppm (4() and !.2 ppm (1()

3. Deduce the structure of each of the follo'ing compounds in the basis of their spectral and molecular formula. a) C8H10 1.! ppm (triplet# %() !.4 ppm (5uarter# ! () 2.1 ppm (broad singlet# 3() b) C4H6Cl4 %./ ppm (doublet# 1() 1.4 ppm (triplet. !()

( )*+

4. (o' many different types of hydrogens (in different environments) are there in the follo'ing compounds$ a) 16 chloropropane chloropropane d) !6 chloropropene b) !#!6dimethylpropane e) cis61# %6dichloropropene c) phenol d) !6

f) (&)61#%6dibromopropene.

2. 7n unkno'n compound having molecular formula C4H8O e8hibits the follo'ing I+ and ( )*+ data. "ive the structure of this compound based on these spectra# indicating the salient features of each spectrum. I+:
1

121. cm61 (strong# single band)

( )*+ : - 1.. (broad# t # %()# - !.1 (broad# s# %() # - !.3 ( 5t.# !()

0. 9ropose a structure that is consistent 'ith the follo'ing spectral data. *:: *; at m<z = 2% I+:
1

%%3. cm61 ('eak# single band) - 1..3 (broad# s # 1 ()# - 1.13 ( t# 4 () # - !.43 ( 5t.# 1()

( )*+ :

/. The mass spectrum of a hydrocarbon sho's a molecular ion at m<z =10!# and the 1 ( )*+ spectrum has t'o signals. - !./ (singlet# 1 ()# - 2.! (singlet# 1. (). 9ropose a structure for this compound. 1.. >or each compound belo'# tell ho' many types of none5uivalent protons there are.
Br CH3 a) CH3 b) Br c)
( CH3)3 C

O C N

CH2CH3 CH2CH3

11. ?yclohe8ane and !6he8ene both have molecular formula C6H10. (o' 'ould you use infrared spectroscopy to distinguish bet'een the t'o compounds$ 9lease e8plain your ans'er.

1!.The molecular formula for an unkno'n compound is CxHyO( MW = 60). Data for the 1( )*+# infrared and mass spectra for this compound are sho'n belo'. @sing the spectral and analytical information provided# determine the structure for this compound.
A

1%. The molecular formula for an unkno'n compound is CxHyO. Data for the 1( )*+# infrared and mass spectra for this compound are sho'n belo'. @sing the spectral and analytical information provided# determine the structure for this compound.

11. The molecular formula for an unkno'n compound is CxHyO3. Data for the 1( )*+# infrared and mass spectra for this compound are sho'n belo'. @sing the spectral and analytical information provided# determine the structure for this compound.

13. The molecular formula for an unkno'n compound is CxHyO2. Data for the 1( )*+# infrared and mass spectra for this compound are sho'n belo'. @sing the spectral and analytical information provided# determine the structure for this compound.

ANS'ERS CHAPTER 12&13- (MS, IR, NMR -Practice Exercises) CHEM 2425 Dr Pa!"a#a$ % Dr C!eri& % Dr Desse$s 1. a) m/e = 172 b) m/e = 91 c) d)

2. a) C5H10O D.U. = 5 10/2 +1 = 1 (db) carbon ! "ro#$ ( C = O)

3%&en'anone or D(e') !$en'ane b) C*H7N D.U. = 7 7/2 + 1/2 + 1 = + ( 1 ben,ene r(n" - 1 'b)

Ben, !) dr(de c) C7H1.O D.U. = 7 1./2 +1 =

(carbon ! "ro#$ C = O)

2% He$'anone or $en' !me') ! /e'one 3. a) C*H1* D.U. = * 1*/2 + 1 = 0 (0(n"!e bond) (CH3)3 C C (CH3)3 b) C.H9Br D.U. = . 9/2 % 1 /2 + 1 = 0 (0(n"!e bond) (CH3)3 C Br a) 2-2-3-3 % 1e'rame') ! b#'ane b) ' B#' ! brom(de

.. a) C+H* D.U. = + */2 + 1 = 3 ('2o ' $e0 $ro'on0) b) C+H10Br2 D.U. = + 10/2 + 1 = 2 ( '2o do#b!e bond0) a) 1-.% C c!o)e3ad(ene b) 2-5 He$'ad(ene

5. a) C*H10 b) C.H+ C!.

D.U. = * 10/2 + 1 = . (Ben,ene r(n") D.U. = . +/2 % ./2 + 1 = 0 (0(n"!e bond)

CH2C! CHC! CH C! CH2C! +. a) CH3 CH2 % CH2 C! (3 ' $e0 H40) b) CH3 C (CH3)2 CH3 (1 ' $e0 H40) c) ( . ' $e0 H40 ) d) CH3 CHC!% CH3 (2 ' $e0 H40) e) CH3 CC! = CH2 (2 ' $e0 H40)

5) ( 3 ' $e0 H-0)

") ( 3 ' $e0 H-0)

7. C.H*O D.U. = . */2 + 1 = 1 ( db bond - carbon ! "ro#$- C=O- 1710 cm%1)

2 B#'anone or 6') !me') ! /e'one

*. 789

m/, = 77 77 %1. = 59 59/12 = + C - 10 H - 1 N C.H10N D.U. = . 10/2 +1 = 0 :; 9 3350 cm%1 am(ne C N CH3 CH2 NH CH2 CH3 D(e') !am(ne 9. m/e = 1*2 1*2/12 = 1. C - 1. H C1.H1. D.U. = 1. 1./2 + 1 = * ( 2 ben,ene r(n") D(e') !ben,ene 10. a) 2 b) 2 c) 11. U0e :; :; 9 c c!o)e3ane 3000 3100 cm%1 and :;9 2 He3ene 1+.0 1+*0 cm%1 12. C3H O (7< = +0) +0 1+ = .. ../12 = 3 C - *H - 1 O C3H*O D.U. = 3 */2 +1 = 0 (0(n"!e bond) :; 3100 cm%1 %OH "ro#$- CH3 CHOH CH3 2 $ro$ano! - (0o$ro$ ! a!co)o! - (0o$ro$ano! 13. C3H O (7< = *+) *+ 1+ = 70 70/12 = 5 C - 10H - 1 O C5H10O D.U. = 5 % 10/2 +1 = 1 ( db- carbon ! "ro#$ C=O- 1710 cm%1)
/

3%7e') !%2%b#'anone or (0o$ro$ !me') ! /e'one 1.. C3H O3 (7< = 130) 130 .* = *2 *2/12 = + C - 10H - 3 O C3H*O3 D.U. = + 10/2 +1 = 2 ( 2 db0 - 2 C=O )

15. C3H O2 (7< = 13*) 13* 32 = 10+ 10+/12 = * C - 10H - 2 O C*H10O2 D.U. = * 10/2 +1 = . ( Ben,ene r(n")

1.