ORGANIC CHEMISTRY
ORGANIC CHEMISTRY
5th Edition
ISBN: 9781259977596
Author: SMITH
Publisher: MCG
bartleby

Concept explainers

bartleby

Videos

Textbook Question
Book Icon
Chapter 13, Problem 13.62P

Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH 3 forms compound A . A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm 1 , in addition to C H stretching absorptions. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152, and a peak in its IR spectrum at 1680 cm 1 in addition to C H stretching absorptions.

Chapter 13, Problem 13.62P, 13.62 Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of

(a) Identify the structures of A and B

(b) Draw a mechanism for the conversion of citronellol to isopulegone.

(c) Draw a mechanism for the conversion of isopulegone to B .

Blurred answer
Students have asked these similar questions
Please use hand drawn structures when needed
B. Classify the following amino acid. Atoms other than carbon and hydrogen are labeled. a. acidic b. basic C. neutral C. Consider the following image. Which level of protein structure is shown here? a. primary b. secondary c. tertiary d. quaternary D. Consider the following image. H RH H HR H R HR HR RH Which level of protein structure is shown in the box? a. primary b. secondary R c. tertiary d. quaternary コー R
Briefly answer three from the followings: a. What are the four structures of the protein? b. Why is the side chain (R) attached to the alpha carbon in the amino acids is important for the function? c. What are the types of amino acids? And how is it depend on the (R) structure? d. Write a reaction to prepare an amino acid. prod

Chapter 13 Solutions

ORGANIC CHEMISTRY

Ch. 13 - Benzene, toluene, and p-xylene BTX are often added...Ch. 13 - Prob. 13.12PCh. 13 - Prob. 13.13PCh. 13 - Prob. 13.14PCh. 13 - Prob. 13.15PCh. 13 - How do the IR spectra of the isomers cyclopentane...Ch. 13 - Problem 13.17 How do the three isomers of...Ch. 13 - Problem 13.18 What functional groups are...Ch. 13 - Problem-13.19 What are the major IR absorptions in...Ch. 13 - Problem-13.20 What are the major IR absorptions in...Ch. 13 - Problem-13.21 Which of the following possible...Ch. 13 - Problem-13.22 Propose structures consistent with...Ch. 13 - 13.23 What major IR absorptions are present above ...Ch. 13 - Problem-13.24 The mass spectrum of the following...Ch. 13 - Prob. 13.25PCh. 13 - Which compound gives a molecular ion at m/z= 122,...Ch. 13 - Propose two molecular formulas for each molecular...Ch. 13 - Propose four possible structures for a hydrocarbon...Ch. 13 - Problem-13.29 What is the molecular formula for...Ch. 13 - Problem-13.30 Propose a molecular formula for rose...Ch. 13 - 13.31 Match each structure to its mass spectrum Ch. 13 - 13.32 Propose two possible structures for a...Ch. 13 - 13.33 What cations are formed in the mass...Ch. 13 - 13.34 and have the same molecular ion in the...Ch. 13 - 13.35 For each compound, assign likely...Ch. 13 - Prob. 13.36PCh. 13 - 13.37 Propose a structure consistent with each...Ch. 13 - 13.38 A low-resolution mass spectrum of the...Ch. 13 - 13.39 Primary alcohols often show a peak in their...Ch. 13 - 13.40 Like alcohols, ethers undergo α cleavage by...Ch. 13 - 13.41 Which of the highlighted bonds absorbs at...Ch. 13 - 13.42 What major IR absorptions are present above ...Ch. 13 - 13.43 How would each of the following pairs of...Ch. 13 - 13.44 Morphine, heroin, and oxycodone are three...Ch. 13 - 13.45 Reduction of cyclohex-2-enone can yield...Ch. 13 - Prob. 13.46PCh. 13 - 13.47 Match each compound to its IR spectrum Ch. 13 - 13.48 Propose possible structures consistent with...Ch. 13 - A chiral hydrocarbon X exhibits a molecular ion at...Ch. 13 - 13.50 A chiral compound has a strong absorption...Ch. 13 - 13.51 Treatment of benzoic acid with followed by...Ch. 13 - 13.52 Treatment of benzaldehyde with in aqueous ...Ch. 13 - Prob. 13.53PCh. 13 - 13.54 Reaction of 2-methylpropanoic acid with ...Ch. 13 - 13.55 Reaction of pentanoyl chloride with lithium...Ch. 13 - Prob. 13.56PCh. 13 - 13.57 Treatment of anisole with and forms P,...Ch. 13 - 13.58 Reaction of with forms compound ,...Ch. 13 - Problem-13.59 The carbonyl absorption of an amide...Ch. 13 - Prob. 13.60PCh. 13 - Problem-13.61 Explain why a ketone carbonyl...Ch. 13 - 13.62 Oxidation of citronellol, a constituent of...
Knowledge Booster
Background pattern image
Chemistry
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
SEE MORE QUESTIONS
Recommended textbooks for you
  • Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305080485
    Author:John E. McMurry
    Publisher:Cengage Learning
    Text book image
    Organic Chemistry
    Chemistry
    ISBN:9781305580350
    Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
    Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305080485
Author:John E. McMurry
Publisher:Cengage Learning
Text book image
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Mass Spectrometry; Author: Professor Dave Explains;https://www.youtube.com/watch?v=hSirWciIvSg;License: Standard YouTube License, CC-BY