4UVEZ(VJEFBOE4UVEFOUhT4PMVUJPOT
.BOVBMGPS0SHBOJD$IFNJTUSZ
4FWFOUI&EJUJPO
Prepare for your exams
Study with the several resources on Docsity
Earn points to download
Earn points by helping other students or get them with a premium plan
Guidelines and tips
Prepare for your exams
Study with the several resources on Docsity
Earn points to download
Earn points by helping other students or get them with a premium plan
Community
Ask the community
Ask the community for help and clear up your study doubts
University Rankings
Discover the best universities in your country according to Docsity users
Free resources
Our save-the-student-ebooks!
Download our free guides on studying techniques, anxiety management strategies, and thesis advice from Docsity tutors
Paula Y. Bruice - Study Guide and Student's Solutions Manual for Organic Chemistry, Exercises of Organic Chemistry
Organic Chemistry International Edition, Paula Bruice
Typology: Exercises
2020/2021
1 / 896
This page cannot be seen from the preview
Don't miss anything!
On special offer
Often downloaded together
Related documents
Partial preview of the text
Download Paula Y. Bruice - Study Guide and Student's Solutions Manual for Organic Chemistry and more Exercises Organic Chemistry in PDF only on Docsity!
4UVEZ(VJEFBOE4UVEFOUhT4PMVUJPOT
.BOVBMGPS0SHBOJD$IFNJTUSZ
4FWFOUI&EJUJPO
Table of Contents
4QFDUSPTDPQZ1SPCMFNT
Paula Y. Bruice 1
3FNFNCFSJOH(FOFSBM$IFNJTUSZ&MFDUSPOJD4USVDUVSFBOE#POEJOH
Paula Y. Bruice 55
"DJETBOE#BTFT$FOUSBMUP6OEFSTUBOEJOH0SHBOJD$IFNJTUSZ
Paula Y. Bruice 77
41&$"-501$*Q) Q,B BOE#VGGFST
Paula Y. Bruice 95
"O*OUSPEVDUJPOUP0SHBOJD$PNQPVOET/PNFODMBUVSF 1IZTJDBM1SPQFSUJFT BOE
3FQSFTFOUBUJPOPG4USVDUVSF
Paula Y. Bruice 115
*TPNFST5IF"SSBOHFNFOUPG"UPNTJO4QBDF
Paula Y. Bruice 143
"MLFOFT4USVDUVSF /PNFODMBUVSF BOEBO*OUSPEVDUJPOUP3FBDUJWJUZt5IFSNPEZOBNJDTBOE
,JOFUJDT
Paula Y. Bruice 171
5IF3FBDUJPOTPG"MLFOFT5IF4UFSFPDIFNJTUSZPG"EEJUJPO3FBDUJPOT
Paula Y. Bruice 193
5IF3FBDUJPOTPG"MLZOFTt"O*OUSPEVDUJPOUP.VMUJTUFQ4ZOUIFTJT
Paula Y. Bruice 233
%FMPDBMJ[FE&MFDUSPOTBOE5IFJS&GGFDUPO4UBCJMJUZ Q,B BOEUIF1SPEVDUTPGB3FBDUJPO
Paula Y. Bruice 251
41&$"-501$**.PMFDVMBS0SCJUBM5IFPSZ
Paula Y. Bruice 301
4VCTUJUVUJPO3FBDUJPOTPG"MLZM)BMJEFT
Paula Y. Bruice 309
4ZOUIFUJD1PMZNFST
Paula Y. Bruice 851
1FSJDZDMJD3FBDUJPOT
Paula Y. Bruice 873
*OEFY 889
1. Determine the structure of the straight-chain pentanol that produces the mass spectrum shown here.
m/z
Relative Intensity
2. The mass spectrum of an ether is shown here. Determine the molecular formula of the ether that would
produce this spectrum and then draw possible structures for it.
m/z
Relative Intensity
From Spectroscopy Problems of Study Guide and Solutions Manual for Organic Chemistry , Seventh Edition. Paula Yurkanis
Bruice.
4. Which of the following compounds gives the mass spectrum shown here?
m/z
Relative Intensity
N
O
O H 2 N
5. An unknown acid underwent a reaction with 1-butanol. The product of the reaction gave the mass spectrum
shown here. What is the product of the reaction, and what acid was used?
m/z
Relative Intensity
6. Identify the compound with molecular formula C 9 H 10 O 3 that gives the following IR and
H NMR spectra.
A
B
S
O
R
B
A
N
C
E
T
R
A N S M I T
T
A
N
C
E
WAVENUMBERS
7. Identify the compound with molecular formula C 5 H 11 Br that gives the following
H NMR spectrum.
10. Identify the compound with molecular formula C 6 H 14 O that gives the following IR and
H NMR spectra.
A B S O R B A N C E
% T R A N S M I T T A N C E
WAVENUMBERS
11. Identify the compound with molecular formula C 4 H 9 Br that gives the following
H NMR spectrum.
12. Identify the compound with molecular formula C 6 H 12 that gives the following IR and
H NMR spectra.
A B S O R B A N C E
% T R A N S M I T T A N C E
WAVENUMBERS
13. Identify the compound with molecular formula C
H
O that gives the following
H NMR spectrum.
16. Identify the compound with molecular formula C 4 H 6 O that gives the following IR and
H NMR spectra.
A B S O R B A N C E
% T R A N S M I T T A N C E
WAVENUMBERS
17. Identify the compound with molecular formula C 7 H 8 BrN that gives the following
H NMR spectrum.
18. The
H NMR spectra of 1-chloro-3-iodopropane and 1-bromo-3-chloropropane are shown here. Which
compound gives which compound spectrum?
a.
b.
19. Identify the compound with molecular formula C 4 H 8 O that gives the following
H NMR spectrum.
22. Identify the compound with molecular formula C 7 H 6 O that gives the following
H NMR spectrum.
23. The two
H NMR spectra shown here are given by constitutional isomers with molecular formula C 3 H 7 Br.
Identify each isomer.
a.
b.
24. An unknown alkene with molecular formula C 8 H 16 undergoes ozonolysis. Only one product is formed. The
IR and
H NMR spectra of the product are shown here. What is the product? What alkene produced this
product?
A B S O R B A N C E
% T R A N S M I T T A N C E
WAVENUMBERS
offset 2.
27. A compound with the following IR spectrum was formed by a reaction with 1-propyne. If the number of
carbons in the reactant and product is the same, what compound is formed and what reaction conditions
produced this compound?
A B S O R B A N C E
% T R A N S M I T T A N C E
WAVENUMBERS
28. Identify the compound with molecular formula C 4 H 8 O 2 that gives the following
H and
C NMR spectra.
CDCl
QE-
Offset: 0.4 ppm.^ ∼2.6 ppm.
29. Identify the compound with molecular formula C 4 H 8 O 2 that gives the following
H NMR spectrum.
30. Identify the compound with molecular formula C 9 H 11 NO that gives the following
H NMR spectrum.
31. Identify the compound with molecular formula C 9 H 10 O 2 that gives the following
H NMR spectrum.