Organic2b - Cycloalkanes Many organic compounds contain...

Info iconThis preview shows pages 1–11. Sign up to view the full content.

View Full Document Right Arrow Icon
Cycloalkanes Many organic compounds contain cyclic or ring structures: carbohydrates nucleotides in DNA and RNA antibiotics testosterone OH O penicillin G CH 2 C NH O N S CO 2 H O
Background image of page 1

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Cycloalkanes Cycloalkanes: alkanes that contain three or more carbons arranged in a ring C n H 2n
Background image of page 2
Cycloalkanes Cycloalkanes are named using: prefix “cyclo” alkane base name Examples: a cycloalkane with 5 carbons in the ring: cyclopentane a cycloalkane with 10 carbons in the ring: cyclodecane
Background image of page 3

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Naming Substituted Cycloalkanes To name substituted cycloalkanes: Use the cycloalkane for the base name Identify substituents using name and position no number is needed if only one substituent is present CHCH 3 CH 3 isopropylcyclohexane
Background image of page 4
Cycloalkanes For 2 or more substituents, number the ring carbons to give the lowest possible numbers for the substituted carbons If numbering could begin with either substituent, start with the one that is first alphabetically. CH 3 CH 2 CH 3 3 1 2 4 5 6 1-ethyl-3-methylcyclohexane
Background image of page 5

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Cycloalkanes When the acyclic portion of the molecule contains more carbons than the cycloalkane, the cyclic portion is named as a cycloalkyl substituent. 3-cyclopropyl-2,6-dimethylheptane
Background image of page 6
Cycloalkanes Example: Name the following cycloalkanes. CH 3 CH 2 CH 3 CH 3 Cl
Background image of page 7

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Cycloalkanes Example: Draw the following cycloalkanes. sec-butylcyclooctane 1,1,3,3-tetramethylcyclohexane
Background image of page 8
Cycloalkane Conformations Cycloalkanes containing 3 - 20 carbons have been synthesized. Rings with 5 or 6 carbons are the most common WHY? Recall that all alkanes contain C - C single bonds that are formed by the overlap of sp 3 hybrid orbitals tetrahedral geometry ideal bond angle = 109.5 o
Background image of page 9

Info iconThis preview has intentionally blurred sections. Sign up to view the full version.

View Full DocumentRight Arrow Icon
Cycloalkane Conformations In cycloalkanes the best overlap (strongest bond) between the sp 3 hybrid orbitals will occur when bond angle = 109.5 o In some cycloalkanes, bond angles other than 109.5 o lead to angle strain and less than optimum overlap of the sp 3 hybrid orbitals Angle strain: the strain associated with bond angles that are smaller or larger than the ideal value
Background image of page 10
Image of page 11
This is the end of the preview. Sign up to access the rest of the document.

This note was uploaded on 01/19/2012 for the course CH 101 taught by Professor Sutcliffe during the Spring '08 term at University of Texas at Austin.

Page1 / 40

Organic2b - Cycloalkanes Many organic compounds contain...

This preview shows document pages 1 - 11. Sign up to view the full document.

View Full Document Right Arrow Icon
Ask a homework question - tutors are online