ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
2nd Edition
ISBN: 9780393664034
Author: KARTY
Publisher: NORTON
expand_more
expand_more
format_list_bulleted
Question
Chapter 4, Problem 4.73P
Interpretation Introduction
Interpretation:
The reason for more stability of
Concept introduction:
In monosubstituted compounds, the equatorial substituted conformer is more stable than the axial conformer due to 1, 3 diaxial interactions. But this depends on the substituent present on it. If the substituent is a hydroxyl group (OH group) present in axial position and can form hydrogen bonding with adjacent or near atoms like oxygen, then it prefers to occupy the axial position only.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
(a) Draw a three-dimensional line structure of (5R,6Z)-6,7-dichloro-5-hydroxynon-6-enal. Place the aldehyde group on the right-hand side of your drawing.(b) Give the Cahn-Ingold-Prelog priority order of the four groups (-OH, -H, -(CH2)3CHO, -C4H5Cl2) at the C5 stereocentre (Highest 1 > 2 > 3 > 4 Lowest).
Are the compound names below representative of prochiral or not prochiral molecules? Label them accordingly.
3-pentanone
3-methylbutanal
2-butanone
cyclopentanecarbaldehyde
Rank the following groups in order of decreasing priority.
−C≡CH, −CH(CH3)2, −CH2CH3, −CH=CH2
Chapter 4 Solutions
ORGANIC CHEMISTRY E-BOOK W/SMARTWORK5
Ch. 4 - Prob. 4.1PCh. 4 - Prob. 4.2PCh. 4 - Prob. 4.3PCh. 4 - Prob. 4.4PCh. 4 - Prob. 4.5PCh. 4 - Prob. 4.6PCh. 4 - Prob. 4.7PCh. 4 - Prob. 4.8PCh. 4 - Prob. 4.9PCh. 4 - Prob. 4.10P
Ch. 4 - Prob. 4.11PCh. 4 - Prob. 4.12PCh. 4 - Prob. 4.13PCh. 4 - Prob. 4.14PCh. 4 - Prob. 4.15PCh. 4 - Prob. 4.16PCh. 4 - Prob. 4.17PCh. 4 - Prob. 4.18PCh. 4 - Prob. 4.19PCh. 4 - Prob. 4.20PCh. 4 - Prob. 4.21PCh. 4 - Prob. 4.22PCh. 4 - Prob. 4.23PCh. 4 - Prob. 4.24PCh. 4 - Prob. 4.25PCh. 4 - Prob. 4.26PCh. 4 - Prob. 4.27PCh. 4 - Prob. 4.28PCh. 4 - Prob. 4.29PCh. 4 - Prob. 4.30PCh. 4 - Prob. 4.31PCh. 4 - Prob. 4.32PCh. 4 - Prob. 4.33PCh. 4 - Prob. 4.34PCh. 4 - Prob. 4.35PCh. 4 - Prob. 4.36PCh. 4 - Prob. 4.37PCh. 4 - Prob. 4.38PCh. 4 - Prob. 4.39PCh. 4 - Prob. 4.40PCh. 4 - Prob. 4.41PCh. 4 - Prob. 4.42PCh. 4 - Prob. 4.43PCh. 4 - Prob. 4.44PCh. 4 - Prob. 4.45PCh. 4 - Prob. 4.46PCh. 4 - Prob. 4.47PCh. 4 - Prob. 4.48PCh. 4 - Prob. 4.49PCh. 4 - Prob. 4.50PCh. 4 - Prob. 4.51PCh. 4 - Prob. 4.52PCh. 4 - Prob. 4.53PCh. 4 - Prob. 4.54PCh. 4 - Prob. 4.55PCh. 4 - Prob. 4.56PCh. 4 - Prob. 4.57PCh. 4 - Prob. 4.58PCh. 4 - Prob. 4.59PCh. 4 - Prob. 4.60PCh. 4 - Prob. 4.61PCh. 4 - Prob. 4.62PCh. 4 - Prob. 4.63PCh. 4 - Prob. 4.64PCh. 4 - Prob. 4.65PCh. 4 - Prob. 4.66PCh. 4 - Prob. 4.67PCh. 4 - Prob. 4.68PCh. 4 - Prob. 4.69PCh. 4 - Prob. 4.70PCh. 4 - Prob. 4.71PCh. 4 - Prob. 4.72PCh. 4 - Prob. 4.73PCh. 4 - Prob. 4.1YTCh. 4 - Prob. 4.2YTCh. 4 - Prob. 4.3YTCh. 4 - Prob. 4.4YTCh. 4 - Prob. 4.5YTCh. 4 - Prob. 4.6YTCh. 4 - Prob. 4.7YTCh. 4 - Prob. 4.8YTCh. 4 - Prob. 4.9YTCh. 4 - Prob. 4.10YTCh. 4 - Prob. 4.11YTCh. 4 - Prob. 4.12YTCh. 4 - Prob. 4.13YTCh. 4 - Prob. 4.14YTCh. 4 - Prob. 4.15YTCh. 4 - Prob. 4.16YTCh. 4 - Prob. 4.17YTCh. 4 - Prob. 4.18YTCh. 4 - Prob. 4.19YTCh. 4 - Prob. 4.20YTCh. 4 - Prob. 4.21YTCh. 4 - Prob. 4.22YTCh. 4 - Prob. 4.23YTCh. 4 - Prob. 4.24YTCh. 4 - Prob. 4.25YT
Knowledge Booster
Similar questions
- Provide a perspective structure for (2R,3R)-2-bromo-3-hexanol.arrow_forwardArrange the following group in order of increasing priority. Q) -CH3 -H -Br -CH2CH3arrow_forwardA 1, 2-cis disubstituted cyclohexane, such as cis-1, 2-dichlorocyclohexane, must have one group axial and one group equatorial. Explain.arrow_forward
- 8. Consider 1-bromo-2-methylpropane. Draw a Newman projection of the following (when viewed directlyalong the C1-C2 bond) a. staggered conformation of lowest energyb. eclipsed conformation of highest energyarrow_forwardRank the following groups in order of decreasing priority. −COOH, −CH2OH, −H, −CHOarrow_forwardAssign a priority order (from least to highest priority) to each of the following sets of groups: I. -OCH II. -NH(CH3)2 III. CH2NH2 IV. -OH A. IV, I, III, II B. III, II, IV, I C. II, III, IV, I D. III, IV, I, IIarrow_forward
- The trans diaxial geometry for the E2 elimination in chlorocyclohexane. Define this ?arrow_forwardRank the following groups in order of decreasing priority. a.−F, −NH2, −CH3, −OH b.−CH3, −CH2CH3, −CH2CH2CH3, −(CH2)3CH3 c.−NH2, −CH2NH2, −CH3, −CH2NHCH3 d.−COOH, −CH2OH, −H, −CHO e.−Cl, −CH3, −SH, −OH f.−C≡CH, −CH(CH3)2, −CH2CH3, −CH=CH2arrow_forwardline angle structural form of 5-cyclobutyl-2-cyclopropyl-6,8-diethyl-3,7,7-trimethyldecanearrow_forward
- Is C-O ester of 3-chloro-4’-methoxychalcone conjugated (talking about the H3CO attatched to the benzene ring)? Can you explain your answer?arrow_forwardComplete the sentence. Hyperconjugation describes how a carbocation is stabilized when the electrons of ____ donate electron density into____. A. a pi bond / an eclipsed C:H bond B. radical / the adjacent pi bond C. a double bond / the positive carbon D. a sigma bond / an empty p orbitalarrow_forwardFor each alkene, indicate the direction of the dipole moment. For each pair, determine which compound has the largerdipole moment.(a) cis-1,2-difluoroethene or trans-1,2-difluoroethene(b) cis-1,2-dibromoethene or trans-2,3-dibromobut-2-enearrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning